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$92

3 BR / 2 BA / Sleeps 8

7 Reviews

$92

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Family Friendly Executive Bay**Discounts Available**

3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 7 Reviews

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Reviews

(7)

Beautiful three bedroom bay side townhouse with private beach access in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise! Come and relax at our beautiful townhome in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(7)

Wonderful

Left on Jul 20, 2013 for a stay in June 2013

This rental by far was one of the best rentals we have stayed at. The location and the house were perfect! The house is very large and everything you can imagine has been supplied. The pool, community center, tennis courts and complex in general were beautiful and well maintained. Really good experience!

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$133

3 BR / 2 BA / Sleeps 7

TURTLE TIME - Florida Keys vacation rentals
1 / 16

$133

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TURTLE TIME

3 BR / 2 BA / Sleeps 7 | Quick view

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Minimum Rental: 1 Month Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunroom overlooking the canal. You'll find this …
  • Internet Access
  • Balcony or terrace
  • Parking
  • Grill
  • Refrigerator
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$150

3 BR / 3 BA / Sleeps 8

2 Reviews

$150

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Fisherman's Dream - Ocean Front House with Dock

3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 2 Reviews

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Reviews

(2)

Welcome to our slice of paradise! Come and relax at our beautiful 3-bedroom home in the Florida Keys. Our home is located in Tavernier, the Sport Fishing Capital of the World. It is a private, gated home directly on the water with a small pier & fishing/boat dock. Our two-story home has master bedroom with a king bed …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(2)

Right on the water

Left on Nov 23, 2014 for a stay in July 2014

This property is very comfortable. Clean and well kept. I loved sitting outside overlooking the waterway. You can even bring your boat!

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$333

3 BR / 3 BA / Sleeps 6

5 Reviews

$333

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Open water in Florida Keys with beautiful sunsets

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 5 Reviews

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Reviews

(5)

Private residence on Duck Key. 2 bedrooms and 2 baths upstairs with a seperate one bedroom one bath apartment downstairs. Apartment has own kitchen and family room. Private dock with heated pool. Ocean kayak and fishing rods included. Catch tarpon right off the dock. House extensively landscaped for total …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly

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Reviews

(5)

The best vacation ever

Left on Oct 31, 2010 for a stay in August 2010

This home is the perfect place to vacation. It has all the amenities you could ask for. Beautiful kitchens, comfortable living areas and wonderful sleeping accomodations. My children and I could not have asked for more. We spent our days swimming in the ocean and relaxing by the pool. The fishing was outstanding. We caught several large tarpon, sharks and baracudda. There are lights under the …

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$193

3 BR / 4 BA / Sleeps 6

2 Reviews

$193

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Packer Retreat: A beautifully renovated "Conch" house

3 BR / 4 BA / Sleeps 6 | Quick view
“ Very Good ” 2 Reviews

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Reviews

(2)

30 DAY MINIMUM RENTAL Packer Retreat is a beautifully renovated "Conch" house with many architectural touches in the charming historic district. Designed to bring the outdoors in, this home features a bright living room with cathedral ceilings & tall French doors opening to the pool & garden area. Nicely decorated …
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(2)

Great house needs updating

Left on Jun 18, 2009 for a stay in February 2009

Packer retreat is a great house. So great I am renting it in 2010. The layout and outdoor space is unusually large for Key West. And the home is very private and quiet. the location is within walking distance to Duval and White streets.

The home is beautifully decorated but needs to be "freshened" up. The sofas and carpets are dirty. the kitchen has very little equipment (1 pan, no serving…

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$157

3 BR / 2 BA / Sleeps 6

Bay Front Condo, Marina & Dockage in Islamorada,FL - Florida Keys vacation rentals
1 / 31

$157

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Bay Front Condo, Marina & Dockage in Islamorada,FL

3 BR / 2 BA / Sleeps 6 | Quick view

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Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This rental property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, heated pool, private beach, basketball and sand volleyball …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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$173

3 BR / 2 BA / Sleeps 6

3 Reviews

$173

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Elizabeth Retreat: A three bedroom historic home in Old Town

3 BR / 2 BA / Sleeps 6 | Quick view
“ Very Good ” 3 Reviews

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Reviews

(3)

30 DAY MINIMUM RENTAL Walk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just two blocks from Duval Street, it is a quick walk or bike ride to all of Key West's attractions, including it's close proximity to the Historic Seaport area. This is an lovingly restored eyebrow 3 …
  • Internet Access
  • A/C or climate control
  • Patio
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(3)

A month in Key West

Left on Jun 18, 2009 for a stay in January 2009

We had an absolutely delightful time! We have been renting homes in the Keys for years and found this to be our best experience yet. The folks at Rent Key West were so helpful - really stayed on top of everything and went out of their way to accomodate our schedule on check in and check out. The house was absolutely lovely and clearly well cared for. We liked it so much, we are coming back …

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$133

3 BR / 2 BA / Sleeps 6

1 Reviews

$133

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108 West Plaza Del Sol - 28 Night Minimum

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

Cozy, canalfront home at MM 74 in Islamorada's desirable Port Antigua (Lower Matecumbe Key) with quick Florida Bay access and a short ride to the Atlantic Ocean. The bed rooms are located in a separated, quiet part of the house, while the living, dining, and kitchen are open for enjoying each other's company. …
  • Waterfront
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Perfect!!!

Left on Aug 06, 2013 for a stay in July 2013

We spent a month at this house with the family. The location was perfect - especially if you have a boat. (If you do not, there are several companies nearby that will deliver one to you). Regardless, it's worth every dime just to sit on the balcony and watch the tarpon and manatees frolic in the waterway out back.

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$215

3 BR / 2 BA / Sleeps 7

2 Reviews

$215

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Gorgeous Keys Water Front Home with Private Dock and Ramp

3 BR / 2 BA / Sleeps 7 | Quick view
“ Excellent ” 2 Reviews

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Reviews

(2)

Water Front home, located Oceanside in Lower Matecumbe key, Islamorada mile marker 73, (The Sport Fishing Capital of the World). 15' wood dock and 12’ wide ramp, so bring your own boat and enjoy the sun!! Easy canal access to the ocean. Maximum boat size is 27'. Only 1 boat allowed. There is a covered fish cleaning …
  • Ocean or water views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Great Getaway!

Left on Dec 09, 2014 for a stay in June 2014

This property was great! It was nicely stocked, very comfortable beds. I loved being on the water! Excellent place to stay! I will return again next summer.

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$167

3 BR / 2 BA / Sleeps 8

1 / 16

$167

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30 night minimum stay requirement. The Palms - 3 Bedroom House with a Swimmi

3 BR / 2 BA / Sleeps 8 | Quick view

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Located on a quiet street in the Meadows of Key West; a tranquil residential neighborhood located just behind the Key West Historical district. This home offers you a two bedroom one bathroom main house with a separate one bedroom cottage with a full bathroom. The private pool and outdoor deck area is in between the …
  • Internet Access
  • A/C or climate control
  • Linens Provided
  • Microwave
  • Satellite or cable TV
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$167

3 BR / 3 BA / Sleeps 8

1 / 19

$167

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30 night minimum stay requirement. Waterfront Escape - 3 Bedroom House on Ca

3 BR / 3 BA / Sleeps 8 | Quick view

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Located in Big Coppitt is this secluded, waterfront paradise. This 3 bedroom, 3 bathroom house features a private pool. Relax in the grand outdoor patio area overlooking the pool and canal. Each of the three bedrooms has its own private bathroom. Located on the ground floor is the living room, dining area, kitchen and…
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Linens Provided
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$112

3 BR / 2 BA / Sleeps 6

2 Reviews

$112

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KEY LARGO YACHT CLUB 8

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 2 Reviews

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Reviews

(2)

Minimum Rental: 1 Month Exceptional 3 story townhouse located in a quiet oceanfront complex with heated pool and marina. Inspiring ocean views from two balconies and a ground level patio to BBQ. Protected marina and deeded boat slip easily accommodates a boat up to 30' (33' from bow to engine.) Boat lift will …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Patio
  • Parking
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(2)

Private gated condos with boat parking, pool and tennis court

Left on Jul 27, 2013 for a stay in July 2013

This condo was spacious, well maintained and included a host of community amenities. There was a pool, tennis and basketball court. It was centrally located to Key Largo, but far enough off the path to create a quiet and comfortable environment. The neighbors were friendly. There was laundry, fishing and a pool table within the condo. Best of all, there was a boat lift associated with the …

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$400

3 BR / 3 BA / Sleeps 8

1 Reviews

$400

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Oasis (28 Day Minimum Only)

3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

****This house cannot rent for less than 28 days, per County Ordinance**** Ahhhh...Ocean Front...Pool...Dockage...It's all hear at Oasis. Oasis is located at Mile Marker 75.6, in beautiful Islamorada. This Beautiful three bedroom, three bath home will sleep 8 people very Comfortably. Besides the bedrooms there are …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Perfect Honeymoon

Left on May 02, 2012 for a stay in September 2011

Me & my Husband stayed here for our Honeymoon in Sept. 2011. We love the "get away from it all" feel, and this place delivered. When we arrived the very first day, we found a pretty decent size conch shell washed up on shore. Guess the tenant decided to move out, so we kept it. Every morning we woke to the ocean through the glass walls of the master bedroom. We walked the shore every morning…

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$380

3 BR / 3 BA / Sleeps 6

3 Reviews

$380

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75333 Overseas Hwy

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 3 Reviews

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Reviews

(3)

Exceptional oceanfront home equipped with a sandy beach and forever views! Exquisite design and rich appointments compliment this oceanfront home in Lower Matecumbe, (mile marker 75, South Islamorada). You will enjoy private terraces from each bedroom overlooking picturesque sunrises and panoramic views of the open …
  • Internet Access
  • Microwave
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Heaven on Earth

Left on Jan 30, 2013 for a stay in December 2012

My husband and I rented this home for the week of Christmas. We also invited our respective parents. This is the most peaceful home in Islamorada. Centrally located to the upper and lower keys.

There home is well appointed with everything you need except for the groceries and tolietries that you will need. All appliances work well and the home is in excellent condition.

Freewheeler realty…

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$173

3 BR / 4 BA / Sleeps 8

3 Reviews

$173

Inquire

Casa Alegria - a Bahamian style conch house

3 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

30 DAY MINIMUM RENTAL Welcome to Casa Alegria! An extended vacation at this Bahamian style conch house is sure to bring you happiness and joy! As you approach the front of the house you'll notice ample off-street parking on either side (a rarity in Old Town!) as well as an easy place to park bicycles. You can park…
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

paradise

Left on Apr 24, 2014 for a stay in January 2014

We were fortunate enough to stay in this immaculate and welcoming retreat. We loved swimming in the pool and riding the bikes around town. We could not have asked for a more perfect place to make our vacation more fabulous!!!! Love...love...love!

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$275

3 BR / 3 BA / Sleeps 7

1 / 22

$275

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Exciting marina-front living! 113 Mariners Club

3 BR / 3 BA / Sleeps 7 | Quick view

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Pristine villa overlooking world-class marina... The excitement of marina-front living can be found right here at Mariners Club Key Largo. Overlooking the marina waterfront in this upscale gated community lies Villa 113. This unique, ground floor location was designed to accentuate the experience of dockside life …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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$200

3 BR / 2 BA / Sleeps 7

1 / 25

$200

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SEA GRAPE

3 BR / 2 BA / Sleeps 7 | Quick view

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MINIMUM STAY: 28 DAYS FABULOUS BEACH HOUSE with sea grape trees on three sides and the ocean on the other! This home is located directly on the Atlantic Ocean with a sandy beach big enough to take lovely morning walks. Wait for the tide to go out and take your chair and umbrella out to the exposed sand bar…
  • Ocean or water views
  • Internet Access
  • Patio
  • Parking
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$150

3 BR / 2 BA / Sleeps 6

1 / 1

$150

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127 Tequesta - 28 Night Minimum

3 BR / 2 BA / Sleeps 6 | Quick view

Details

N/A
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$243

3 BR / 0 BA / Sleeps 6

11 Reviews

$243

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Bay Harbour Complex

3 BR / Sleeps 6 | Quick view
“ Excellent ” 11 Reviews

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Reviews

(11)

Please send us an inquiry or call us for availability. Prices vary on the units. Bay Harbour Condominiums, built in 2003, is a beautiful area with great condos located in Islamorada, mile marker 74, bay-side. Exterior amenities include deep-water boat slips in a protected harbor, lush tropical landscaping, …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible - ask

Details

Reviews

(11)

Excellent. Very nice unit

Left on Aug 23, 2011 for a stay in July 2011

We thorough enjoyed our stat in this unit. It was spotless, had a nice view, and very convenient. We would definitely ask for the same unit next time.

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$193

3 BR / 3 BA / Sleeps 6

1 / 10

$193

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Roland's Repose, comfortable accommodations, # 24B

3 BR / 3 BA / Sleeps 6 | Quick view

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Tastefully decorated 3 bedroom, 3 bath half-duplex. Upgraded with granite counter tops in the kitchen and all 3 baths. The main level of the house is tiled through out and the upstairs master suite is carpeted. The upstairs master suite and the downstairs master bedroom both have king beds. The guest room has a queen …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Suitable for children
  • Suitable for the elderly - ask

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$150

3 BR / 3 BA / Sleeps 6

4 Reviews

$150

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200 Plantation Shores Drive

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 4 Reviews

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Reviews

(4)

A very charming and immaculate 3 bedroom home in Plantation Key. This home has excellent protected deep water dockage. Ocean views from balcony. Easy bay access via Tavernier Creek. Close to resturants and store. CLICK HERE to view photos on a mobile device. Additional amenities include: dock/boat-slip, coffee maker…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Grill
  • Dishwasher
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

Islamorada Getaway

Left on Sep 06, 2012 for a stay in July 2012

The service from Freewheeler Vacations, Inc was above & beyond! Our family rented the Islamorada home for the month of July 2012. The ocean breezes were fantastic! There were only two things I wish would have been better. One, the quality of the cookware and second, the aC cooling of the downstairs bedroom. If these items were to be updated/corrected then this truly would be a perfect vacation …

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$580

3 BR / 3 BA / Sleeps 6

1 / 12

$580

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Tucked away near the Southernmost Point, Louisa's Hideaway is it!

3 BR / 3 BA / Sleeps 6 | Quick view

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Tucked away near the upper end of Duval Street you'll find this stylish, newly renovated three bedroom, three bath home. Thoughtful details are luxuriously appointed to suit the vacation guest looking for privacy and high design. Walk up the brick drive and enter the gate to the palm tree lined path that leads to …
  • Internet Access
  • A/C or climate control
  • Patio
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$250

3 BR / 3 BA / Sleeps 8

1 / 20

$250

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VILLA BELLA 13

3 BR / 3 BA / Sleeps 8 | Quick view

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Minimum Rental: 3-7 Night Minimum Villa Bella is a fabulous 3 BR/3 BA two-story townhouse. This end unit townhome "lives" on the 2nd floor. The kitchen, dining and living areas are all open to each other in a great room with a gorgeous vaulted ceiling. There are 2 bedrooms and 2 baths on this upper level including …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Balcony or terrace
  • Parking
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$470

3 BR / 2 BA / Sleeps 6

38 Reviews

$470

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Coconut Cabana: A restored Old Town home with charm & tropical ambience

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 38 Reviews

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Reviews

(38)

An Old town Key West home, located in the Historic District and just one half a block off Duval Street. Guests are within walking distance of restaurants, the Atlantic Ocean, Southernmost Point of Key West and our sunset piers. All lovingly restored and cared for, this charming 1 & 1/2 story historic home is …
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(38)

Coconut Cabana - Go Nuts!

Left on Jun 18, 2009 for a stay in November 2007

We loved Coconut Cabana! This house was perfect for a "sibling celebration" of my brother's 50th birthday. The house was darling, well equiped and the entire rental process was smooth sailing. There is no place like Key West and this house just off Duval was just where we needed to be. We would highly recommend!

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$450

3 BR / 3 BA / Sleeps 6

35 Reviews

$450

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Villa Paradiso: A unique mid-town paradise

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 35 Reviews

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Reviews

(35)

This mid-town Key West home is newly renovated and beautifully decorated in jewel tones of the Mediterranean. It features three bedrooms and three baths. The open living/kitchen area is decorated with rich tones with tropical accents and soft fabrics. The dining room is outside in the attached pavillion with an ornate…
  • Internet Access
  • A/C or climate control
  • Patio
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(35)

The 3 couples loved this home.

Left on Jun 18, 2009 for a stay in February 2009

We chose the Villa because it advertised 3 bedrooms and 3 baths. I would advertise it as 2.5 bedrooms. However, the space worked out very well for the 6 of us. The home is graciously appointed and easy to live in. The small pool area was a perfect gathering spot. There were other decks and seating areas when each of us choses a bit more privacy. The Villa was within walking distance of the …

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$275

3 BR / 3 BA / Sleeps 8

1 Reviews

$275

Inquire

Got stress?...409 Mariners Club has the power to restore you

3 BR / 3 BA / Sleeps 8 | Quick view
“ Average ” 1 Reviews

Details

Reviews

(1)

Instantly feel the warmth of the island spirit as you enter this inviting 3-bedroom, 3-bath, tri-level townhouse at Mariners Club Resort. Enjoy the relaxing atmosphere the Florida Keys are known for...a perfect setting for family fun or a private romantic get-a-way. Experience the joyful gratitude of the day's …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

Townhouse great, Mariner Club itself disappointing.

Left on Mar 13, 2015 for a stay in March 2015

Townhouse as pictures depicted which is always a relief. Outfitted fine and pretty comfortable furniture. Was very clean on arrival. Kitchen equipped with dozens of wine glasses but not 1 decent frying pan. Appreciated the shampoo/soaps in the bathrooms and the dish soap/sponge provided in the kitchen. Blinds in the living room and master bedroom the cheap plastic strips-did very little to …

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$249

3 BR / 2 BA / Sleeps 8

10 Reviews

$249

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Steps to Duval, Old Town Charm -Grand Bahama Suite

3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 10 Reviews

Details

Reviews

(10)

Just steps away from shops, restaurants, and the excitement of Duval Street, yet set on a quiet side street in a world of its own. With 3 bedrooms and 2 Baths, The Grand Bahama Suite has plenty of room for a large gathering or group of friends. Experience endless sunshine and the incomparable charm found only in …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(10)

Amazing location!!!

Left on Nov 05, 2013 for a stay in August 2013

Location was wonderful one block block of Duval street, 3 of us shared the rental each had their own bedroom and there were 2 baths, and we 3 grown men having the 2nd bath was very valuable. The backyard area while not being the most beautiful thing in the world was still a great place to sit out and have a few drinks with friends old and new, our upstairs neighbors were great people and we …

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$370

3 BR / 2 BA / Sleeps 6

42 Reviews

$370

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Whitehead House: A unique two story home beside the Audubon House

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 42 Reviews

Details

Reviews

(42)

Whitehead House is a unique two-story single family attached home nestled beside the Audubon House in Old Town Key West. Hidden behind the most photographed "prohibition fence" in Key West, this three bedroom, two bathroom home includes a large sunny pool and patio as well as off street parking (1 space). An outdoor …
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(42)

Hidden Jewel

Left on Jun 18, 2009 for a stay in July 2008

This house is fantastic! The location is awesome - right in the middle of everything!!! Everything you would want was there. House was clean, pool was excellent and off street parking is great! The 2 bedrooms and bathroom downstairs are small, but for the amount of time you really need them, they are fine. I would certainly recommend this house and plan to rent it again.

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$314

3 BR / 2 BA / Sleeps 6

6 Reviews

$314

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La Casa Habana: Beautiful 3 BR on Gulf w Pool

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 6 Reviews

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Reviews

(6)

La Casa Habana is a 3 bedroom , 2 bath house overlooking the Gulf of Mexico on exclusive and private Morton St. on Grassy Key. This house has been extremely popular for over 10 years. It has everything you need for a great vacation-bikes, kayaks, snorkel gear, fishing gear, Cable TV and wifi internet for those rare …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(6)

Great Vacation Home

Left on Mar 12, 2012 for a stay in March 2012

This is a beautifully decorated and comfortable house. It is clean, neat and well organized. The kitchen is well stocked for cooking anything. Everything is well maintained and we got everything we needed. The pool is really nice, and its heated. The hot tub is terrific. The views of the Gulf, especially at sunset ,or the early morning, are magical. This is a great spot for a getaway or a …

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$175

3 BR / 2 BA / Sleeps 8

7 Reviews

$175

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Spacious Top Floor Condo w/ Water View!!

3 BR / 2 BA / Sleeps 8 | Quick view
“ Very Good ” 7 Reviews

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(7)

Top floor suite! Beautifully furnished condo overlooking the aqua-blue waters of the Gulf of Mexico! This 1,700 sq. ft. , custom decorated condominium offers a unique water vista from the living areas. The split floor plan provides privacy as the bedrooms are on each side of the living/dining area. There is a fully …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children - over five
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

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(7)

Great place to stay!

Left on Jul 18, 2013 for a stay in July 2013

We stayed in this condo for a week in July 2013. The condo was clean, spacious and inviting. It was the perfect size for our family. The location was great. We explored up and down the keys, it was great being centrally located. The kitchen was stocked with all of the utensils, plates, cups etc that we needed. Linens were provided, plentiful and clean. My most favorite part about the condo…

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$250

3 BR / 1 BA / Sleeps 6

1 Reviews

$250

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The Cottage (28 DAY MINIMUM)

3 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

****DUE TO A COUNTY ORDINANCE THIS PROPERTY CANNOT RENT FOR LESS THAN 28 DAYS**** You fall in love with The Cottage at first sight. Built in 1935, this once Red Cross building serves as a true historical reflection of the Florida Keys. Both bedrooms overlook the ocean, which is a mere 30 feet from the wrap around …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(1)

COTTAGE @ SCHOONER BAY - ABSOLUTE SOLITUDE AND SUPERB LOCATION

Left on Dec 02, 2013 for a stay in November 2013

We were so lucky to have visited this home during November. We had the whole private gated compound to ourselves and even though we only leased the Cottage, the owners were so gracious to allow us total use of the pool at the Palm house next door. I cannot say enough good things about our entire experience here. It was quiet, our main bedroom was literally 30 feet from the water, it was …

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$132

3 BR / 2 BA / Sleeps 6

1 / 24

$132

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BAYSIDE BREEZE

3 BR / 2 BA / Sleeps 6 | Quick view

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MINIMUM STAY: 30 DAYS NEW HOME (2013) Spend the fall or winter in the Florida Keys! You will love this wonderful 2013 built stilt home. Features include an open living area with gourmet kitchen, stainless steel appliances, including a wine refrigerator and granite counters. The oversized center island in …
  • Internet Access
  • Balcony or terrace
  • Parking
  • Grill
  • Refrigerator
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$340

3 BR / 2 BA / Sleeps 8

8 Reviews

$340

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Hemmingway's Retreat

3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 8 Reviews

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(8)

Welcome To Paradise!!! Located in the heart of Key West this charming 3 bedroom, 2 bathroom house has been completly renovated and includes 50", 42", and 27" flat screen TVs, DVR, and wireless high speed internet. The interior has just been furnished with custom designer furniture by Domestic Home Furnishings. The …
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly

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    Reviews

    (8)

    1211 Catherine St.

    Left on May 10, 2010 for a stay in April 2010

    My wife and I spent time in April at 1211 Catherine St., Key West, FL and had a marvelous time. The house is wonderful expecially the private pool. All that Key West has to offer is within easy walking or cycling distance of the house. The house is beautifully furnished and appointed so much so we spent many days just staying home and relaxing around the pool. One of the bicycles provided had to…

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    $120

    3 BR / 2 BA / Sleeps 6

    1 Reviews

    $120

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    Holidays are fast approaching! Book Now!

    3 BR / 2 BA / Sleeps 6 | Quick view
    “ Poor ” 1 Reviews

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    Reviews

    (1)

    Moon Bay - a gated, private condo community located in the heart of Key Largo at mile marker 104.3. This bayfront complex has a resort feel to it, with landscaped grounds and rental dockage available in the private marina on Florida Bay. This 2 bedroom, 1.5 bath condo is the perfect choice for your Florida Keys …
    • Waterfront
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Suitable for children
    • Suitable for the elderly - elevator access
    • Wheelchair accessible - ask

    Details

    Reviews

    (1)

    WARNING re Construction

    Left on Mar 03, 2015 for a stay in February 2015

    The unit is spacious and comfortable. However, Building A is located directly adjacent to busy US 1. There is no water view from this unit. At the rear of the unit there is a large screened-in lanai that overlooks the parking lot and another building in the complex. It is a very short walk to the pool and waterfront. The internet frequently drops out for short periods.

    At the time we …

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    $275

    3 BR / 2 BA / Sleeps 8

    3 Reviews

    $275

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    Key Largo - Calypso

    3 BR / 2 BA / Sleeps 8 | Quick view
    “ Excellent ” 3 Reviews

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    Reviews

    (3)

    Why rent a hotel in Key Largo when you can stay on board our FABULOUS houseboat rental Calypso. Docked in the heart of Key Largo, your stay on board our boat will be so surreal you won't believe it's a reality! This luxury home on the water, is a boat lovers dream. With 3 bedrooms and a sleeper sofa, this BRAND NEW …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Pet friendly - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    Reviews

    (3)

    Fabulous, fabulous, fabulous!

    Left on Jan 14, 2014 for a stay in December 2013

    The weather was absolutely fabulous. We loved the house boat and found it simply perfect for our needs. Loved the sun deck, the beds were comfortable, and all the amenities were lovely. Since we were down there for a wedding, we really appreciated having the iron and ironing board available - that was a pleasant surprise. The hair blower arrived while were there, so I placed in bathroom cabinet…

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    $400

    3 BR / 3 BA / Sleeps 5

    6 Reviews

    $400

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    You will never want to leave

    3 BR / 3 BA / Sleeps 5 | Quick view
    “ Excellent ” 6 Reviews

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    Reviews

    (6)

    3 bedroom, 2.5 bath home at the end of a quiet private road in Islamorada. Queen bed in the master with a fantastic view of the ocean from your pillow. Two queen beds in the second bedroom with en suite bath The third bedroom is used as an office. From the moment you open the front door you have a view of the ocean …
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Internet Access
    • Washing Machine
    • Pet friendly - ask
    • Suitable for the elderly - ask

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    Reviews

    (6)

    Really Super great place. Have stayed here twice and this place

    Left on Dec 09, 2013 for a stay in December 2013

    We have stayed here twice. Could not ask for a more peaceful and scenic view. Super great place and all of the things that you need. Very clean and very nice. Beautiful inside and out and the owners as nice as the place. Fantastic restaurants within a few miles north or south. One of the nicest little Bass Pro Shops around just a few miles up the road. The sunsets are amazing the mornings are …

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    $245

    3 BR / 2 BA / Sleeps 9

    3 Reviews

    $245

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    Tropical House at relaxing paradise !!!

    3 BR / 2 BA / Sleeps 9 | Quick view
    “ Excellent ” 3 Reviews

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    Reviews

    (3)

    Beautiful 2 story 3 bedroom 2 baths home. Located in Key Largo at MM 103 on the bayside and close to John Pennekamp Park, local shopping, fine restaurants, diving, charter fishing or just swimming with the dolphins! This home has an open water view overlooking the beautiful Florida Keys bay, Relax in this tropical …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly

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    Reviews

    (3)

    A very clean, cozy and tastefully decorated house with a balcony overlooking a canal

    Left on Feb 05, 2014 for a stay in January 2014

    We stayed at the property for 4 nights. It accommodated us (5 adults and 4 kids) nicely - there were three bedrooms, all rooms being decorated very tastefully. Kind size beds in two bedrooms, a large bunk bed in one bedroom and a sofa in the living room. The kitchen was also nice and there was almost everything we needed. Only one thing - there were not enough cups for all of us so we had to buy …

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    $210

    3 BR / 2 BA / Sleeps 8

    5 Reviews

    $210

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    Ocean Front Condo - Lovely View

    3 BR / 2 BA / Sleeps 8 | Quick view
    “ Excellent ” 5 Reviews

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    Reviews

    (5)

    When you arrive, you know you've come somewhere very special. This condo has the most spectacular views of the the Atlantic Ocean and a pristine heated pool. Located on Coco Plum Beach in Marathon, Florida Keys, you're in a secluded yet central base for all Keys sightseeing and activities, if you should want them. …
    • Ocean or water views
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Parking
    • Suitable for children
    • Suitable for the elderly

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    Reviews

    (5)

    The perfect place for our family getaway!

    Left on Oct 06, 2013 for a stay in June 2013

    This condo has an amazing view of the ocean! When we weren't walking on the beach or swimming in the pool it was nice to sit on the patio and just enjoy our surroundings. The place was quite spacious, very clean and pleasantly decorated. Also, it's location was convenient for us to explore local restaurants and shops. We're already planning a return trip next year.

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    $200

    3 BR / 3 BA / Sleeps 6

    8 Reviews

    $200

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    Reel Paradise - Big Pine Key

    3 BR / 3 BA / Sleeps 6 | Quick view
    “ Excellent ” 8 Reviews

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    Reviews

    (8)

    REEL PARADISE, located in Big Pine Key, Florida Keys offers a large open format Keys retreat with vaulted ceilings. 3 bedrooms – King bed master suite – Queen bed master suite and two full beds in a spacious third bedroom, 3 baths, large kitchen, dining room, family room, sitting area, large screen plasma TV in …
    • Waterfront
    • Internet Access
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible

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    Reviews

    (8)

    Comfort & Privacy at Reel Paradise

    Left on Jul 29, 2013 for a stay in September 2012

    Reel Paradise was the perfect place for our Keys trip last year. We completely loved the layout of this house and the comfort and luxury it provided. The entire interior of the house is covered in cedar planks including the interior of the roof. The furniture is all Tommy Bahama and the kitchen has a nice big island to prep and serve all the food we made each night.

    The canal system is …

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    $540

    3 BR / 2 BA / Sleeps 6

    1 / 18

    $540

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    Casa de Cuba:Beautiful home loaded with style and elegance

    3 BR / 2 BA / Sleeps 6 | Quick view

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    Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can't be beat. The home's history is rich; neighboring the historic Gato Cigar factory which is now restored and used as …
    • Internet Access
    • A/C or climate control
    • Patio
    • Parking
    • Grill
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $299

    3 BR / 3 BA / Sleeps 8

    5 Reviews

    $299

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    If paradise has an address...it is Villa 333

    3 BR / 3 BA / Sleeps 8 | Quick view
    “ Excellent ” 5 Reviews

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    Reviews

    (5)

    Mariners Club Resort and Marina is the one of the finest condominium properties in all of The Florida Keys. Mariners Club Resort and Marina is a gated, oceanfront community with deep-water marina and direct ocean access for world-class diving and fishing adventure experiences! Features of this professionally …
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Internet Access
    • Housekeeping Optional
    • Suitable for children - ask
    • Suitable for the elderly - elevator access
    • Wheelchair accessible - ask

    Details

    Reviews

    (5)

    Amazing!

    Left on Mar 03, 2014 for a stay in February 2014

    Gorgeous views all around. We rented this gorgeous and spacious apartment for 3 nights and absolutely loved it. The apartment has all the comforts one would need and more. I'd definitely recommend this to anyone interested in staying in a luxurious, safe, quiet and scenic venue in Key Largo.

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    $250

    3 BR / 3 BA / Sleeps 8

    2 Reviews

    $250

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    Private Keys Paradise

    3 BR / 3 BA / Sleeps 8 | Quick view
    “ Excellent ” 2 Reviews

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    Reviews

    (2)

    Enjoy your own private paradise and have fun in the Keys! This beautiful, clean, spacious and airy vacation rental home is locate in Key Largo "Diving Capital of the World." Key Largo is the first island of the Florida Keys, south of the Florida mainland. The house has three wonderfully decorated and clean bedrooms …
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Internet Access
    • Housekeeping Optional
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (2)

    Couldn't have been more perfect!

    Left on Aug 08, 2014 for a stay in August 2014

    My family and I had an amazing time here! The house was everything that we expected. I will definitely stay here again. The morning sunrise and evening sunsets were spectacular! Our view was superb! I could go on and on but you will not know just how spectacular Key Largo is or how awesome this house is until you book it! Great job!

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    $140

    3 BR / 2 BA / Sleeps 6

    1 / 26

    $140

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    OCEAN BREEZE

    3 BR / 2 BA / Sleeps 6 | Quick view

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    MINIMUM RENTAL: 1 MONTH BEAUTIFUL CANAL FRONT STILT HOME WITH HEATED POOL - For the guest who expects perfection this is it. This is a completely remodeled 3 bedroom/2 bath (2/1 up and 1/1 down) single family home - perfect for one couple or a smaller family. It is conveniently located in Tavernier on a deep and…
    • Shared outdoor pool (unheated)
    • Balcony or terrace
    • Parking
    • Grill
    • Refrigerator
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $258

    3 BR / 2 BA / Sleeps 6

    1 / 19

    $258

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    Charming 3bedroom/2bath home in the Florida Keys

    3 BR / 2 BA / Sleeps 6 | Quick view

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    Relax in our traditional keys style stilt home. The home is located on a channel with immediate access to the Atlantic Ocean. The concrete dock allows for easy access and quick drive to the open water. With the ocean at your whim, finding your favorite spots for fishing, lobstering, diving, and snorkeling has never …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children
    • Suitable for the elderly - ask

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    $300

    3 BR / 3 BA / Sleeps 6

    6 Reviews

    $300

    Inquire

    Indigo Reef Villa 59

    3 BR / 3 BA / Sleeps 6 | Quick view
    “ Excellent ” 6 Reviews

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    Reviews

    (6)

    This spacious three bedroom, two and a half bath Villa will make you feel right at home. Each bedroom has it’s own television, with a 60” flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony. The kitchen…
    • Central heating
    • Balcony or terrace
    • Fitness Room
    • Parking
    • Books
    • Pet friendly - ask
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (6)

    A perfect paradise in Marathon, Fl

    Left on Feb 18, 2014 for a stay in February 2014

    My husband and I just had to escape the bitter cold and unending snow in Ct. We just couldn't stand it one more day.. How very fortunate we were to be able to book a flight and beautiful condo in Marathon, Fl on short notice. I received a call back almost immediately upon emailing an inquiry. Although we had been to Marathon before we had never seen this property at Indigo Reef. How very lucky we…

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    $429

    3 BR / 3 BA / Sleeps 8

    8 Reviews

    $429

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    Villa Pamela - Tropical Paradise

    3 BR / 3 BA / Sleeps 8 | Quick view
    “ Excellent ” 8 Reviews

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    (8)

    3 bedroom 'suites" villa on the Gulf of Mexico on exclusive and private Morton Street on beautiful Grassy Key, next to Marathon, the "heart of the Keys". Each private suite has its own bathroom-completely renovated in the fall of 2010, its own seating area and flatscreen TV. Beautifully landscaped grounds with private…
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Internet Access
    • Washing Machine
    • Smoking allowed - ask
    • Suitable for children
    • Suitable for the elderly

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    (8)

    Can not wait to go back!

    Left on Feb 08, 2011 for a stay in November 2010

    I stayed at Villa Pamela over 4 months ago and I still think about this vacation. The home was perfect, it had every ammenity you could ask for. The kitchen was stocked with everything you could possibly need, the outdoor areas provided plenty of entertainment and seating. The heated pool was great. Fishing of the dock was a blast. I would definitely rent this unit again.

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    $133

    3 BR / 2 BA / Sleeps 6

    1 Reviews

    $133

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    MATECUMBE JEWEL

    3 BR / 2 BA / Sleeps 6 | Quick view
    “ Excellent ” 1 Reviews

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    Reviews

    (1)

    Minimum Rental: 1 Month You will love jewel of a home! Located in Lower Matecumbe, this charming canal front home offers a swimming pool, dockage, direct access to the ocean, covered fish cleaning station, a screened lanai, inviting décor and comfortable accommodations. It is located on a dead-end street in a …
    • Internet Access
    • Patio
    • Parking
    • Grill
    • Refrigerator
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Our Lobster Trip to the Keys

    Left on Aug 24, 2013 for a stay in August 2013

    My family and I stayed at the Matecumbe Jewel in the month of august for Lobster season. The home shows even better than the photos, was clean, well furnished and kept. We could not have asked for better accomodations while on our first Lobstering vacation! The service by Keys Holiday Rental was a+++! We will certainly be back! Thanks again to everyone at Keys Rental and the owners of the …

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    $267

    3 BR / 3 BA / Sleeps 7

    6 Reviews

    $267

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    Luxurious 3bd/3bth Villa - Your Keys Escape

    3 BR / 3 BA / Sleeps 7 | Quick view
    “ Excellent ” 6 Reviews

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    Reviews

    (6)

    Come to the Florida Keys and enjoy living in luxury at 'Blue Heaven'. There are blue skies, crystal clear blue water, calm tropical breezes at 'Blue Heaven' every day. This beautiful new three bedroom, three bath villa has 2,000 square feet on 2 levels with under cover parking. It is located in the new gated community…
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Internet Access
    • Housekeeping Optional
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - ask

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    Reviews

    (6)

    Great place to spend your vacation

    Left on Sep 29, 2013 for a stay in September 2013

    My husband and I had an amazing time in Marathon with our friends. The home was such a beautiful place and perfectly clean. The beds were so comfortable and the kitchen was well stocked with all the amenities we needed for our stay. The home was equipped with linens, towels, a cooler, and much more! We enjoyed relaxing upstairs in the lounge area with the views of the Gulf during the beautiful…

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    $250

    3 BR / 2 BA / Sleeps 10

    2 Reviews

    $250

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    Key Largo Paradise!!!

    3 BR / 2 BA / Sleeps 10 | Quick view
    “ Excellent ” 2 Reviews

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    Reviews

    (2)

    Beautiful 3 story 3 bedroom 2 baths home. Locate in key largo at MM 101 is on a canal which opens up to beautiful Tarpon Basin Bay with access to the Atlantic Ocean. Minutes from beautiful Penny Camp National Underwater Park. Close to local shopping, fine restaurants or just swimming with the dolphins! Come to the …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (2)

    nice place

    Left on Aug 20, 2014 for a stay in July 2014

    We enjoy staying at this place.

    Very big place, very clean.

    I got my deposit back.

    I will visit again

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    $325

    3 BR / 3 BA / Sleeps 8

    1 / 17

    $325

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    Life in Paradise in Coral Lagoon, 3 BDRM, Sleeps 8

    3 BR / 3 BA / Sleeps 8 | Quick view

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    Thank you for your interest in our stunning town home in Coral Lagoon, Trip Advisors #1 rated resort in beautiful Marathon, FL. Built in 2007, this two story 3 BR /2.5 BA is the perfect residence for your next vacation. For the Boating and Fishing Enthusiasts, this residence there is also a 35' boat slip available …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask
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