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$99

3 BR / 2 BA / Sleeps 8

7 Reviews

$99

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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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(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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$132

3 BR / 2 BA / Sleeps 6

BAYSIDE BREEZE - Florida Keys vacation rentals
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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$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

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(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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$150

3 BR / 3 BA / Sleeps 8

1 Reviews

$150

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Fisherman's Dream - Ocean Front House with Dock

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

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Reviews

(1)

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

(1)

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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$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). 40' dock and 12’ wide ramp, so bring your own boat and enjoy the sun!! Easy canal access to the ocean. There is covered fish clean area. Minutes away from Anne's Beach with it's white …
  • 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

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(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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$400

3 BR / 3 BA / Sleeps 6

Eliza's Jewel is a charming property close to White Street. - Florida Keys vacation rentals
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$400

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Eliza's Jewel is a charming property close to White Street.

3 BR / 3 BA / Sleeps 6 | Quick view

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30 DAY MINIMUM Two charming Conch houses are joined together at Eliza’s Jewel, an elegant three-bedroom home in Old Town Key West. Located in a quaint neighborhood just steps from the restaurants, shops and art galleries of White Street, Eliza’s Jewel combines beautifully preserved historical architecture with …
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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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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(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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$173

3 BR / 4 BA / Sleeps 8

3 Reviews

$173

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Casa Alegria - a Bahamian style conch house

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

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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

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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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$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 …
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  • Suitable for children - ask
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(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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$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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$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

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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

34 Reviews

$450

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Villa Paradiso: A unique mid-town paradise

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 34 Reviews

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Reviews

(34)

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

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Reviews

(34)

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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$179

3 BR / 3 BA / Sleeps 8

1 / 12

$179

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Quick Ocean access in Key Colony Beach

3 BR / 3 BA / Sleeps 8 | Quick view

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This 2100 sq ft bright and spacious property is located just 3 houses back from the canal entrance to Shelter Bay, which provides quick access to the Ocean or Gulf. It also includes membership to the Cabana Club, which is oceanfront with a beach, heated pool, activities restaurant and bar. Key Colony Beach has …
  • Internet Access
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  • Patio
  • Grill
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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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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$133

3 BR / 2 BA / Sleeps 6

1 / 25

$133

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"SEMINARY ST HIDEAWAY" 3 Bd 2 Bth Home w/ Private Pool

3 BR / 2 BA / Sleeps 6 | Quick view

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***Due to licensing restrictions, this home requires a minimum stay of 28 nights*** This newly renovated 3 bedroom "home away from home" sits right smack in the middle of the Key West island and is a short distance to everywhere you will want to go during your vacation! Located on Seminary St, in a quiet …
  • Internet Access
  • A/C or climate control
  • Grill
  • Linens Provided
  • Satellite or cable TV
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$187

3 BR / 2 BA / Sleeps 6

1 Reviews

$187

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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

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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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$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

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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

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(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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$133

3 BR / 2 BA / Sleeps 7

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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$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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$186

3 BR / 2 BA / Sleeps 8

1 / 36

$186

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BRAND NEW 3 bedroom, 2 bath with dockage and great introductory pricing!!!!!!

3 BR / 2 BA / Sleeps 8 | Quick view

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A paradise is immersed when entering Ramrod Key. It offers you a close relationship with the nature displaying an exuberant vegetation bordering the sea water canals. Ramrod Key is known as Breezeswept because of the breezes that sweep it through. This is a well located house, walking distance to a Looe Key Tiki Bar…
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Grill
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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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

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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 …
  • Internet Access
  • 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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$243

3 BR / 3 BA / Sleeps 6

11 Reviews

$243

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Bay Harbour A-304- 7 night minimum

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

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Reviews

(11)

Brilliant views of Sandy Cove Yacht Basin and the Atlantic Ocean, combined with 50ft of deep-water dockage (uses 50amp) complete this 3BD/2.5BA Bay Harbour Condos penthouse. This spacious unit features updated furnishings, a full kitchen with stainless steel appliances and granite countertops, a spacious screened …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - elevator access
  • Wheelchair accessible - ask

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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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$150

3 BR / 2 BA / Sleeps 6

1 / 1

$150

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194 Gulfview Drive - 28 Night Minimum

3 BR / 2 BA / Sleeps 6 | Quick view

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Fantastic Home in the Fantastic Location of Port Antigua in Lower Matecumbe (South Islamorada)! This canal-front home offers 3 bedrooms, 2 bathrooms with tasteful and comfortable decorations. The home has an open floor plan, tile floors throughout, and very nice balcony overlooking the water. Click here to view this …
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Grill
  • Dishwasher
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$350

3 BR / 3 BA / Sleeps 8

2 Reviews

$350

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Bay Harbour Waterfront Condo

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

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Reviews

(2)

Revel in the beauty of the morning sunrise as you relax on your own, private lanai while sipping your morning coffee, or enjoy a meal al fresco to the sound of the waves and gulls. This piece of paradise is sure to become your favorite home away from home. This beautifully furnished and spacious condo offers all the …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

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(2)

Great Vacation!

Left on Dec 22, 2014 for a stay in October 2014

We have stayed at Bay Harbor several times in this condo and love it. The condo feels like home and has everything you would ever need during your stay The complex is very well maintained and the pool area is great for relaxing, the slip for your boat is also a plus. Everything from the great fishing, snorkeling and great restaurants, there is something for everyone in the family. This will …

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$150

3 BR / 1 BA / Sleeps 1

4 Reviews

$150

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200 Plantation Shores Drive

3 BR / 1 BA / Sleeps 1 | 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

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(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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$117

3 BR / 2 BA / Sleeps 6

1 / 1

$117

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258 Mohawk St - 28 Night Minimum!!!!!!!

3 BR / 2 BA / Sleeps 6 | Quick view

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Looking for an extended stay in the Upper Keys that won't bust the bank? If so, you need not search any farther than this cozy, modern home on Islamorada's Plantation Key. Located in the popular Indian Waterways neighborhood, this three-bedroom/two-bath house is a great value at just $3,500 per month. The residence …
  • Waterfront
  • Internet Access
  • A/C or climate control
  • Porch
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$150

3 BR / 2 BA / Sleeps 8

1 / 8

$150

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30 night minimum stay requirement. Manatee Manor

3 BR / 2 BA / Sleeps 8 | Quick view

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Just 10 miles from Old Town you’ll find a seaside neighborhood that recalls Lower Keys life in the good old days, when you would go fishing in the morning, have lunch and a beer (or two) at Geiger Key Marina, fish some more in the afternoon then cook some of the catch out on your deck with a few cold ones. And while…
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Deck
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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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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Reviews

(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

Details

Reviews

(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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$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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$175

3 BR / 3 BA / Sleeps 8

1 Reviews

$175

Inquire

BLUE WATER RETREAT

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

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Reviews

(1)

Minimum Rental: 1 Month Location, location, location! This home has it all - ocean side Lower Matecumbe location, totally remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost every room in this home. It is located on a canal …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Patio
  • Parking
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Blue Water = Everything that you want

Left on Jul 15, 2013 for a stay in July 2013

This place delivers.

You never really know what you are going to get from looking at a website and photos. I just stayed there July/2013 and this place is great, everything is new and clean. Most of all the house is on a peninsula that looks at the ocean from all sides and is just a few miles south of most of that main attractions in Islamorada giving the home a calm but close feel. Also working…

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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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$150

3 BR / 3 BA / Sleeps 8

1 / 25

$150

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Higgs Beach Hacienda - 3 Bed 2.5 Bath Monthly Rental Near Beach. Huge Yard!

3 BR / 3 BA / Sleeps 8 | Quick view

Details

Tucked into a quiet residential neighborhood, this renovated home is the perfect getaway for a family or group of friends looking to experience the Key West island life! This 3 bedroom home is on Patricia St, just a block from the scenic biking bath that runs along the Atlantic side of the island; very close (less …
  • Internet Access
  • A/C or climate control
  • Linens Provided
  • Dishwasher
  • Microwave
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$286

3 BR / 3 BA / Sleeps 6

4 Reviews

$286

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130 Bayview Isle Dr

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

Details

Reviews

(4)

Great neighborhood located on Snake Creek. 2 bedroom/2 bath upstairs with a bunkroom and bath downstairs. An outdoor hot tub and sundeck complement the excellent deep water dockage and easy bay or ocean access. There is room for about a 36 foot boat or less. Mile Marker 86, Bayside. VACATION RENTAL LICENSE: VR-069 …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

I loved this place!

Left on Nov 02, 2010 for a stay in October 2010

Both the home and the location in Islamorada were perfect! I spent a week at 130 Bayview Isle and it was exactly what I hoped it to be. It was incredibly quiet and felt like home. If the home is for rent next year, I will absolutely rent it again. Awesome place!

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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

Details

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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$243

3 BR / 3 BA / Sleeps 6

1 Reviews

$243

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Bay Harbour C-312

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

Details

Reviews

(1)

Beautiful 3 bedroom 2.5 bath luxury condo at MM 74.5 Complex comes complete with two tennis courts, weight room, pool, dockage, fish cleaning station, and free Wi-Fi at community clubhouse. The condo boasts some amaizing views of the Clear Blue waters of the Atlantic Ocean looking over Sea Oats Beach. Relax on your …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Vacation of a lifetime!

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

Vacation started off when we arrived at Bay Harbour. Upon walking into our unit, we were thrilled! We will never stay any where else. Absolutely a wonderful condo and so worth the money!

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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

Details

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

Details

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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$329

3 BR / 3 BA / Sleeps 6

6 Reviews

$329

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138 Bayview Isle

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

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Reviews

(6)

Modern canal home with views of Snake Creek. The property is completely fenced in. Third level master suite with private master balcony. Well furnished with all the extras. Easy ocean or bay access and dockage up to 50 feet. Open floor plan with regulation pool table and screened in porch. This home's entertainment …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(6)

Perfect location

Left on May 27, 2011 for a stay in May 2011

Other then having to Clean-up the bug's it was great.

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$236

3 BR / 2 BA / Sleeps 6

2 Reviews

$236

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155 Azalea Street

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

Details

Reviews

(2)

Plantation Key canal home. Nice new home with screened porch and pool table! Delightfully furnished for a comfortable stay. Excellent outdoor entertaining space, great for soaking in the hot tub, gazing at fish in the canal, having cocktails under the Chickee, or for the kids to run around and play. Great dockage with…
  • Waterfront
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Porch
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Loved the place and location!!

Left on Aug 11, 2013 for a stay in July 2013

We completely enjoyed our stay. Plenty of room for 6 ppl to sleep. Nice sized kitchen and dining area. We stayed with two young children and they loved it. Great location for both gulf access and on land access to grocery, dining and all. We can't wait to go back.

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$107

3 BR / 2 BA / Sleeps 8

1 / 11

$107

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Boaters Paradise in Ramrod Key

3 BR / 2 BA / Sleeps 8 | Quick view

Details

10 minutes to the OCEAN - DEEP WATER CANAL READY FOR LOBSTER SEASON!!!!! 3 bedroom 2 bath Stilt house on a canal. Nice screened in porch (mosquito proofed) to relax in the evening. 10 minutes to the Ocean!! Just 25 minutes to Key West. Walking distance to Looe Key Reef Resort and Tikki Bar or to Boondocks. 2 …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children

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$183

3 BR / 2 BA / Sleeps 6

1 / 13

$183

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On Hemingway's Rounds ~ Monthly Rental

3 BR / 2 BA / Sleeps 6 | Quick view

Details

Key West has long been loved for its playful spirit, forever attracting all genres of fun-loving artists, musicians, and writers. In recognition for the island’s historical humor, we have fondly named this beautiful upscale home, On Hemingway’s Rounds. Paying tongue-in-cheek homage to Papa’s …
  • Housekeeping Optional
  • A/C or climate control
  • Stereo or CD player
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$175

3 BR / 3 BA / Sleeps 6

1 / 17

$175

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Mediterranean Caribbean Villa ~ Monthly Rental

3 BR / 3 BA / Sleeps 6 | Quick view

Details

Tucked behind a breathtaking tropical garden wall this spectacular Mediterranean Caribbean vacation rental home reflects a dynamic blend of contemporary Mediterranean with Caribbean architectural design. Located along one of Key West's most desirable residential streets this "Casa el Paradiso" most …
  • Housekeeping Optional
  • A/C or climate control
  • Stereo or CD player
  • Telephone
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$288

3 BR / 2 BA / Sleeps 6

1 / 10

$288

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Southernmost Retreat- 1 Block from Duval

3 BR / 2 BA / Sleeps 6 | Quick view

Details

Just 1 short block from Duval Street the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house located Simonton Street. The Southernmost Retreat is located in the Simonton Historic Cottages enclave and is surrounded by fine restaurants, art galleries, shopping and in the center of the Old…
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • A/C or climate control
  • Porch
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

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$250

3 BR / 2 BA / Sleeps 8

3 Reviews

$250

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Fisherman's Paradise with a 30 Ft Boat Slip

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

Details

Reviews

(3)

Fishermans Paradise at Oceanside Isle Condominiums with 1,800 Square Feet of Living Space, on Long Key, which is a Secluded Island with direct access to both Atlantic Ocean and the Bay of Florida through Channel #5. Expansive Master Suite and with Large Tub & walk-in shower. Relax on your one of your private decks, …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(3)

Our Honeymoon!

Left on Apr 24, 2013 for a stay in February 2013

Our Honey Moon was very special at Fisherman's Paradise. Everything was top shelf and facilities are the best. The care that Bob Hubert paid to our every need was very special to us and the memories will last forever!

Sincerely,
Paget and Bennie McGee

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$300

3 BR / 3 BA / Sleeps 6

14 Reviews

$300

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Island life! 410 Mariners Club Key Largo

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 14 Reviews

Details

Reviews

(14)

Trip Advisor/Flip Key Award-winning tri-level townhouse overlooking luxurious lagoon pool to ocean! Screened patios ground floor, poolside as well as from main living area and the master suite. 2 king beds and two singles...granite kitchen and bath countertops, custom oak cabinetry, stainless appliances...luxurious …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(14)

relaxing

Left on Jun 26, 2011 for a stay in June 2011

We had a wonderful time. The place nice and clean. We stayed in Mariners Club 410. The kitchen was stocked well.

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$195

3 BR / 2 BA / Sleeps 8

1 / 15

$195

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Walk to Sombrero Beach

3 BR / 2 BA / Sleeps 8 | Quick view

Details

Escape to gorgeous Marathon, Florida Keys for a romantic getaway or a fun family retreat. For families with young children this Keys Vacation home is located just two blocks away from beautiful Sombrero Beach with a children`s playground, baseball diamond, volleyball net, picnic areas and roped swim area for all to …
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Fitness Room
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$258

3 BR / 3 BA / Sleeps 6

1 / 44

$258

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Largo Vista ~ Waterfront, Boat Slip, Rooftop Deck

3 BR / 3 BA / Sleeps 6 | Quick view

Details

Fabulous, like-new, waterfront vacation home located in the Heart of Key Largo! You'll love the convenient location, the boat slip, and the peek-a-boo ocean view from the fabulous roof top deck! This stunning vacation home is ideal for vacationers planning to enjoy either land or sea activities or both! Travelers can…
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$275

3 BR / 3 BA / Sleeps 8

1 / 31

$275

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

3 BR / 3 BA / Sleeps 8 | Quick view

Details

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

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$167

3 BR / 3 BA / Sleeps 6

4 Reviews

$167

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"TOBAGO GRANDE" Monthly Rental Home w/ Private Pool Just 1 Block To Duval

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

Details

Reviews

(4)

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Tobago House is just steps from restaurants, night life, Hemingway's House, and the 'Southernmost Point' of the United States. This home offers an open, airy floor plan with old style pine walls and floors, cathedral ceilings …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Patio
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

Perfect in Every Way!

Left on Nov 14, 2013 for a stay in October 2013

I stayed at Tobago house for the month of October and loved it! This was my 2nd stay - my best friend rented the house for 6 weeks in the spring of 2012 - and it was even better than I remembered. The house is well appointed with all the things one needs to set up house for a few days or for several weeks.

The location is prime and provides easy access to Duval street and all the shops and …

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$227

3 BR / 3 BA / Sleeps 6

2 Reviews

$227

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"VILLA AZUL" Luxurious Monthly Home w/ Pvt Pool, Deck & Gorgeous Interior.

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

Details

Reviews

(2)

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** You will certainly enjoy this wonderful historic home with recent renovations, perfectly placed pool, and plenty of outdoor living space located at 1116 Curry Lane. This home is situated in the heart of Old Town, just 4 blocks …
  • Internet Access
  • A/C or climate control
  • Deck
  • Fitness Room
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Beautiful and comfortable home

Left on Jan 27, 2011 for a stay in December 2008

Villa azul is a wonderfully decorated and appointed home in the historic Old Town section of Key West. The home and grounds were beautiful, serene, private and cozy. It is hard to imagine that this property would not exceed anyone's expectations.

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$275

3 BR / 3 BA / Sleeps 8

15 Reviews

$275

Inquire

Oasis Vacation! 406 Mariners Club Key Largo

3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 15 Reviews

Details

Reviews

(15)

Welcome to this elegant island home in Mariners Club, Key Largo`s premier resort. The open living area, dining room and designer kitchen draw your eyes outside to breathtaking views of the oasis pool and beyond to Rock Harbor and the Atlantic Ocean. This is the vacation we all dream about, clear blue waters, sunny …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(15)

Perfect location and great view!!!

Left on Nov 13, 2012 for a stay in April 2012

The location is key and offers a ton of ammenities including several pools and gym which was important to us.

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