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$99

2 BR / 2 BA / Sleeps 8

2 Reviews

$99

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Newly Renovated Townhouse in Beautiful Executive Bay **Discounts Available**

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

Details

Reviews

(2)

Beautiful two bedroom townhouse on the Bay side with private beach access in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise! Come and relax at our beautiful, newly renovated townhome in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World…
  • 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

Details

Reviews

(2)

Great condo, perfect location!

Left on Jan 02, 2015 for a stay in December 2014

I have two small children and the condo was perfect and comfortable for the entire family. It was nicely remodeled. The pool and dock area were very nice. Security was visible and very friendly. The location was close to everything. The property management service was excellent. We had a wonderful family vacation and will definitely be returning next year!

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$149

1 BR / 1 BA / Sleeps 3

3 Reviews

$149

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SUNSHINE PLACE

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

Details

Reviews

(3)

Minimum Rental: 7 Nights You can have it all – privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people who treasure the tropical atmosphere …
  • Internet Access
  • Patio
  • Parking
  • Grill
  • Refrigerator
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(3)

Awesome place!

Left on Jul 08, 2013 for a stay in July 2013

My wife and I just returned from a weeklong stay at this property. I have to say this is far and away the nicest 1 bedroom rental and as far as I'm concerned a hidden jewel in Islamorada. It is the bottom floor of a 2 story home that has been converted to a rental unit. The upper unit is the occasional getaway of the owner and not available to rent at this time. The property entrance is gated and…

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$63

1 BR / 2 BA / Sleeps 4

1 Reviews

$63

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THE PALMS 417

1 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Minimum Rental: 1 Month Everything in this unit is exquisite - furnishings, linens, updated kitchen, appliances, and bathrooms. Great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and 2 highly acclaimed restaurants. Watch the sun …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Balcony or terrace
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Paradise on the ocean

Left on Apr 15, 2014 for a stay in March 2014

We rented Palm 417 for the month of March 2014. The condo has been very nicely updated and although not direct ocean front view; it does have partial view of the ocean side and a good view of the bay side with amazing sunsets. People in surrounding condos were very friendly; and one condo owner gave us some lovely smoked fish. Some road noise but we soon got used to it as the condo and location …

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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

Details

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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$200

2 BR / 1 BA / Sleeps 4

2 Reviews

$200

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83261 Old Highway

2 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

A quaint bungalow on a not-so-quaint piece of oceanfront land right in the Heart of Islamorada! This home has two bedrooms, two bathrooms, and a lot of Keysy charm. During your stay, you will enjoy such amenities as a fishing dock with Chickee hut (1ft draft), cable television, a kayak, and a white picket fence …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

House with privats beach and fishing pier

Left on Mar 27, 2014 for a stay in March 2014

Great house; really stocked well. Huge property with a grass yard in the front, side and about half grass and sandy beach in the back. Saw a shark, stingrays, spuffer fish and baracuda from the fishing pier. Also a great location; close to everything. May be better for a couple since there is only 1 bathroom; a little tight for a family of four. Really my only complaint is they should put down…

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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

Details

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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$258

2 BR / 3 BA / Sleeps 6

3 Reviews

$258

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Islamorada Luxury Waterfront Condo with Boat Slip

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

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Reviews

(3)

Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club house, fitness center, …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

Details

Reviews

(3)

Wonderful stay at Bay Harbour

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

This condo exceeded our expectations. It was truly a home away from home. It has all the amenities you will need to have a great vacation. The kitchen is fully furnished, the condo is spacious, and the little extras like bikes, tennis rackets, and baseball gloves are an added bonus.

Our family was happy to see a manatee and calf in the water right outside the condo!

Pool was very …

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$117

2 BR / 3 BA / Sleeps 4

2 Reviews

$117

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75190 Overseas Hwy - 28 NIGHT MINIMUM!!!!!!!

2 BR / 3 BA / Sleeps 4 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Great home with an even better view ... come and stay for a month and enjoy the Incredible endless views from the patio. Home is located in the perfect spot for snorkeling, fishing, and diving, and has a protected & private boat basin! Come once and you will see why so many people come back year after year to …
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Grill
  • Dishwasher
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Relaxing

Left on Aug 18, 2011 for a stay in July 2011

The location was great.Mad Dog's & Ziggy's was fabulous! Love shopping at Morada Bay Gallery. The kitchen was ill equipped, who ever heard of a house in the Keys w/o a blender??? Nasty grill. The beach at the house was great. The gate to the house was locked and we were not supplied the key and had to wait for 45 minutes for someone to bring us one.

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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 6

4 Reviews

$150

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200 Plantation Shores Drive

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

Details

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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$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

Details

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

Details

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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$179

2 BR / 2 BA / Sleeps 6

4 Reviews

$179

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BROCK HAUS ON THE GULF

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

Minimum Rental: 7 Nights (Saturday to Saturday) BROCKHAUS ON THE GULF is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the marina. The panoramic open water views from this unit …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Balcony or terrace
  • Parking
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(4)

Great week on Islamorada

Left on Aug 21, 2013 for a stay in August 2013

Just returned from a week at Brockhaus. This was our 4th time staying at this property (although the last time was in 2009) and everything felt very familiar and comfortable. The location is perfect,the views are spectacular, and the convenience of the boat slip right out the door is a huge plus! The 2 bedrooms are comfortable but the town home could use a bit of updating (it hasn't changed a bit…

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$125

1 BR / 1 BA / Sleeps 3

6 Reviews

$125

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Serenity Waterfront-Dock, View, Tiki Hut, spa/hot

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

Details

Reviews

(6)

Located in beautiful Plantation Key, the first Island of Islamorada. An area of all waterfront homes Wifi, boat dock, trailer parking, and all amenities are included also, Lovely Tiki Hut overlooking the water. Plus a huge covered entertainment area complete with dining areas, settee and gas BBQ. Dockage for …
  • Waterfront
  • Hot Tub/Jacuzzi
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(6)

Great owners-average accommodations

Left on Apr 25, 2014 for a stay in April 2014

You've got to like Key Islamarada because it's strictly for boaters and this place has a slip for yours. We booked it because it was one of the few rentals with handicapped access. You will spend most of your time in the covered recreation area, which is a large shaded area and always had a nice breeze while we were there. Some things in the unit could use owner's attention, such as the glued …

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$77

2 BR / 2 BA / Sleeps 5

1 Reviews

$77

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THE PALMS 314

2 BR / 2 BA / Sleeps 5 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Minimum Rental: 1 Month Sensational oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Watch the fishing charter boats as they come and go from Bud and Mary's Marina. You'll be able to see cruise ships as they pass by Alligator Reef and Light House or …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Patio
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Wow, what a beautiful view

Left on Feb 13, 2015 for a stay in January 2015

This condo was clean, nicely furnished and had a view to die for. We really appreciated the washer and dryer in the unit, which most did not have. Also, being on the end we had "the window" in the master bedroom and in the daytime the view would take your breath. However, at night the lights from the parking lot would shine into our bedroom. Alas, with the flip of a switch an outside shutter …

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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

Details

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

Details

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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$600

4 BR / 3 BA / Sleeps 8

1 Reviews

$600

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Latitude

4 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**** Latitude: Freedom of thought or action. No word could better described this Keys Vacation Home. Embrace the serenity of the azure Atlantic Ocean while you relax in the private heated pool. Latitude boasts 2 master suits and two guest rooms. …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

A wonderful week with extended family

Left on Jun 16, 2013 for a stay in June 2013

Our extended family of 8 had a wonderful week at Latitude. The house is modern and immaculate. There was plenty of space and privacy for everyone. We had a great time watching a huge variety of sealife from the dock. We saw nurse and bonnet-head sharks, crabs, puffer fish, a turtle, stingrays and much more. The house was convenient to several very good restaurants (Pierre's, Islamorada Fish …

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$83

2 BR / 2 BA / Sleeps 4

1 / 19

$83

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135 Gulfview Dr - 28 Night Minimum!!!!

2 BR / 2 BA / Sleeps 4 | Quick view

Details

This delightful 2 bedroom, 2 bathroom home is located in Port Antigua (south Islamorada) at the 74 mile marker. While not located directly on the bay, you'll still be able enjoy the homeowners park that has a beach and beautiful sunsets. The home comes equipped with Wi-Fi internet. Click here to view photos on a …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$315

2 BR / 3 BA / Sleeps 4

1 / 1

$315

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Angler's Reef | 130 Anglers Way

2 BR / 3 BA / Sleeps 4 | Quick view

Details

Add some Caribbean spice to your next visit to the Florida Keys. This two-bedroom/two-and-half bath villa sits within Angler's Reef, a charming community of detached town homes that take their inspiration from the architecture of the British West Indies. Located at mile marker 85, on Windley Key, it's the perfect …
  • Ocean or water views
  • Internet Access
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask

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$400

4 BR / 5 BA / Sleeps 8

2 Reviews

$400

Inquire

74920 Overseas Hwy

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

Details

Reviews

(2)

One of a kind bay front estate! This is an absolutely gorgeous estate home offering a gated entrance paved brick driveway, 3,500 sf, 3 bedrooms, 3.5 bathrooms upstars and a bonus 1 bedroom, 1 bathroom apartment downstairs. Enjoy ocean & lagoon views, deep water protected dockage, 2 Great rooms, private master suite, …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • A/C or climate control
  • Telephone
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

The Best

Left on May 29, 2012 for a stay in April 2012

Everything about this property was exactly as represented by Freewheeler. It was spotless and completely ready for our group despite last minute changes to the schedule. We will certainly consider this property and Freewheeler for our future visits to the Keys.

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$100

2 BR / 2 BA / Sleeps 4

1 Reviews

$100

Inquire

VILLA RIOLO

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

MINIMUM STAY: 28 DAYS Villa Riolo is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offering you an opportunity to share their vacation …
  • Internet Access
  • Balcony or terrace
  • Parking
  • Refrigerator
  • Satellite or cable TV
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Fishing Vacation

Left on Aug 13, 2014 for a stay in July 2014

Was a very clean house with all the amenities. I would stay again. Easy access to the Ocean for fishing and plenty of dock for your boat.

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$107

2 BR / 2 BA / Sleeps 4

1 / 23

$107

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BEACON REEF 501

2 BR / 2 BA / Sleeps 4 | Quick view

Details

MINIMUM STAY: ONE MONTH. Exceptional 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Ocean views from the open air balcony. You'll be so glad you have chosen to spend your holiday here. The kitchen was remodeled in 2013 - granite counters, stainless steel appliances, and tray ceiling with …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$215

3 BR / 2 BA / Sleeps 6

16 Reviews

$215

Inquire

Windy Cove Townhomes

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 16 Reviews

Details

Reviews

(16)

Please send us an inquiry or call us for availability. We have a couple of units. Located on Windley Key this gated 5 unit complex has the best of the Keys with a private pool, sandy beachy area, and fishing pier with flats boat dockage (drawing 24" or less) located directly on the ocean. Amazing views!. We …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(16)

Absolutely awesome

Left on Jun 21, 2010 for a stay in June 2010

Windy Cove was a wonderful place.
The view was amazing. The location was perfect. We will be staying here again!

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$175

3 BR / 3 BA / Sleeps 8

1 Reviews

$175

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BLUE WATER RETREAT

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

Details

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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$300

2 BR / 2 BA / Sleeps 6

3 Reviews

$300

Book

Islamorada Florida Keys Beautiful 2B 2B Townhouse

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

Details

Reviews

(3)

Vacation in Paradise!!... you will love this fun filled, relaxing townhouse in the beautiful Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach and a …
  • Waterfront
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children

Details

Reviews

(3)

Marvelous Property- First Class All the Way!

Left on Jan 16, 2015 for a stay in December 2014

The Daniels' property was an outstanding vacation rental. It is centrally located in the middle of Islamorada. This is a two story end unit condo that is in perfect, (yes, perfect) condition. There is a roomy master bedroom, 2nd bedroom and a loft (accessible through the master). The living room is expansive, the kitchen is modern, ultra well equipped and easy to use.

I would love …

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$358

4 BR / 3 BA / Sleeps 8

1 / 12

$358

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Blue Harbour

4 BR / 3 BA / Sleeps 8 | Quick view

Details

Village Permit #VR-09-82 You can not rent this property for less than one week. Ahhhh...Ocean Front....Protected Dockage... Blue Harbor is located at Mile Marker 85, in beautiful Islamorada. This Ocean Front four bedroom,three bath home will sleep 8 people very comfortably. (One of the bedrooms is on the ground level…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$100

2 BR / 0 BA / Sleeps 4

1 / 7

$100

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Executive Bay Club

2 BR / Sleeps 4 | Quick view

Details

Please send us an inquiry or call us for availability. Prices vary on the units. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach and a fishing/boat dock. Next …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$63

2 BR / 2 BA / Sleeps 4

1 / 15

$63

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THE PALMS 506

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Description….. MINIMUM STAY: Minimum Rental: 1 Month 5th Floor unit at one of Islamorada's favorite condo complexes. This unit was recently sold and the new owners are beginning to update some of the décor. You'll love the fantastic panoramic ocean views as you relax or dine on the balcony. There's …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask

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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

Details

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 - ask
  • Smoking allowed - ask
  • Suitable for children
  • 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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$358

4 BR / 3 BA / Sleeps 8

4 Reviews

$358

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76004 Overseas Highway

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

Details

Reviews

(4)

Enjoy spectacular sunsets while drinking margaritas on the observation deck of this stunning home nestled back behind swaying palm trees. Large sandy beach and great dock. Interior photos available! Mile Marker 76, Bayside. Home has 2 bedrooms & 2 bathrooms upstairs, and a separate 2 bedroom, 2 bathroom apartment …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

A Week in a Tropical Paradise.

Left on Aug 03, 2010 for a stay in July 2010

We had a fantastic time. Incredible home on the water with boat dock. Plenty of room and privacy. Accommodations were five star. We highly recommend it.

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$100

2 BR / 2 BA / Sleeps 4

2 Reviews

$100

Inquire

Summer Sea Condominium Complex

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Summer Seas is located directly on the Florida Bay is the perfect sunny getaway! The complex is centrally located at mm 88. There is also on-site community laundry, a pool, hot tub, and clubhouse. Islamorada, the "Village of Islands," is widely known as the sportfishing capital of the world. Its islands …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Parking
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Heaven in Islamorada, Florida

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

Rented a 2/2 condo for the month of July 2011.
Great location, nice amenities,clean,wonderful view, friendly staff and condo owners.
Excellent price.
I will definitely do this again soon.

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$143

2 BR / 0 BA / Sleeps 4

3 Reviews

$143

Inquire

Sea Gulls Condominium Complex

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

Details

Reviews

(3)

Please send us an inquiry or call us for availability. Prices vary on the units. Sea Gulls Condominiums, on the shores of the Atlantic Ocean provides vacationers the splendor of the Atlantic waters with luxury living at an affordable price. This perfect family vacation destination offers something to do in, under, …
  • Waterfront
  • Ocean or water views
  • Sauna
  • Internet Access
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Adequate

Left on May 24, 2012 for a stay in April 2012

The condo provided plenty of space for two couples. The complex is quiet. The pool is nice and the meditation beach(tiny) was relaxing. The condo itself was very dated. The beds were comfortable. The living room furniture was stained. The entire condo had an odor but tolerable. Possibly it had not been used for some time, not sure. Smelled musky. The balcony is large and was enjoyable for…

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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

Details

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
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,279

5 BR / 7 BA / Sleeps 10

1 / 13

$1,279

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Kara-Pan

5 BR / 7 BA / Sleeps 10 | Quick view

Details

You can not rent this property for less than one week. The ultimate island experience awaits you at Kara-Pan I. This exquisite, private, two story, Plantation Style home is located on a pristine natural white sand beach with oceanviews that inspire relaxation. The 5 bedroom 7 bath home with a wrap around porch, is …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Suitable for children
  • Suitable for the elderly

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$929

4 BR / 4 BA / Sleeps 10

13 Reviews

$929

Inquire

75731 Overseas Highway

4 BR / 4 BA / Sleeps 10 | Quick view
“ Excellent ” 13 Reviews

Details

Reviews

(13)

Islamorada is the Spiritual Center of the Keys, the Sportfishing Capital of the World, and home to the largest fleet of charter boats in the Keys. Fish deep water or the back bay. Snorkeling and SCUBA sites abound. Restaurants, art galleries, and other shopping are plentiful in Islamorada. Pass through a private …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(13)

Paradise!!!

Left on Jul 14, 2010 for a stay in May 2010

Michelle Sorell was a great help and everything was just perfect. I hated to leave. the property is well maintained and Randy was also nice with all our grandboys that came in to visit while we were there. Thanks again for making our vacation so wonderful.

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$236

3 BR / 2 BA / Sleeps 6

2 Reviews

$236

Inquire

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
  • 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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$208

2 BR / 2 BA / Sleeps 4

2 Reviews

$208

Inquire

75130 Overseas Highway

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Great house in Lower Matecumbe (south side of Islamorada) at the 75 mile marker on the bayside. This house has fabulous sunset views in a nice quiet part of town. There is a small beach area in the back with palm trees giving you a little more privacy. A screened in porch with tables and chairs makes for a great …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Television
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

The view and location was excellent.

Left on May 06, 2011 for a stay in April 2011

The house had most of the amenities I would expect at a beach location. You can't beat the sunsets over the bay!
We snorkeled at Key Largo and took a day trip into key West, so the location was perfect. The area had the best restaurants. We tried them all.
Only complaints were: no outdoor grill, no wine glasses, sheets kept pulling off the bed and rusted beach chairs.

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$350

3 BR / 3 BA / Sleeps 8

3 Reviews

$350

Inquire

Enjoy stunning views of the sunrise from this beautiful Keys condo

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

Details

Reviews

(3)

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

Reviews

(3)

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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$286

3 BR / 2 BA / Sleeps 6

6 Reviews

$286

Inquire

76300 Overseas Highway

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

Details

Reviews

(6)

Enjoy this Bayfront home with a spectacular sunset view, fenced yard and tile throughout the house. Also has great dockage and clean swimming area. Secured wi-fi, local telephone, & cable television (basic) included. VACATION RENTAL LICENSE: VR-039 CLICK HERE to view photos on a mobile device. Additional …
  • Waterfront
  • Internet Access
  • Porch
  • Grill
  • Dishwasher
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(6)

Great views and convenient to the entire Keys chain

Left on Feb 09, 2011 for a stay in December 2010

Great location, fantastic views, great access to the Bay and atlantic. Older home but clean and well maintained. Nicely situated in the Keys for access to Key West to Key Largo. Home had only basic cable and the dish washer did not work but overall would recommend the home. If your looking for luxury, this is not your place but if you want to just experience the keys and all they offer it's …

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$147

2 BR / 2 BA / Sleeps 4

1 / 17

$147

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BEACON REEF 222

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Minimum Rental: 1 Month Extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada. It offers 2 spacious bedrooms, 2 full baths…
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Patio
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$286

3 BR / 3 BA / Sleeps 6

4 Reviews

$286

Inquire

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
  • Suitable for children
  • 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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$279

2 BR / 3 BA / Sleeps 6

1 / 24

$279

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LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

2 BR / 3 BA / Sleeps 6 | Quick view

Details

This beautiful villa has all new furnishings and is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84. Angler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean with 52 colonial detached villas set along quaint streets …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly

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$175

4 BR / 4 BA / Sleeps 8

1 / 36

$175

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164 Plantation Shores Drive - 28 NIGHT MINIMUM

4 BR / 4 BA / Sleeps 8 | Quick view

Details

This is a very spacious and very well-maintained 4 bedroom, 3 bathroom home toward the mouth of the canal on a quiet street in Plantation Key (Tavernier). You and your group will enjoy stunning views from the main level, master suite, & rooftop sundeck. There is approximately 20ft concrete dockage. The home sits on a …
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Grill
  • Dishwasher
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$329

3 BR / 3 BA / Sleeps 6

7 Reviews

$329

Inquire

137 Leserra Lane

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

Details

Reviews

(7)

Beautiful designer appointed Oceanside canal home located at the Mile Marker 76.5 in Lower Matecumbe (South part of Islamorada). This home is the second one in on a point and has a great ocean view. Fully loaded kitchen with dishwasher, microwave, coffee maker, toaster, and blender. There are two flat panel TV's in …
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Grill
  • Dishwasher
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(7)

We had a very relaxing and fun-filled vacation

Left on Jul 15, 2010 for a stay in June 2010

The house is in a great location in Lower Matecumbe. Robbie's restaurant is only one mile away which we went to three times (twice by car, once by boat). We also went to anne's Beach twice with our dogs. The house is great for pets, the yard is fenced in and there is plenty of room for the dogs to run around.

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$77

2 BR / 2 BA / Sleeps 4

1 / 14

$77

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THE PALMS 402

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Minimum Rental: 1 Month Pure pleasure will be yours in this beautifully remodeled and immaculate condo. You'll love the uncluttered and modern décor along with the recent renovations. Enjoy the picturesque views of Alligator Reef and the Atlantic Ocean from this 4th floor balcony. Watch the fishing boats …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Balcony or terrace
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$200

1 BR / 1 BA / Sleeps 2

6 Reviews

$200

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Islamorada Waterfront Paradise 1

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

Details

Reviews

(6)

**We do not use the optional calendar feature on this listing. ** This is a very popular rental, so book your preferred week well in advance of peak season! I reply to EVERY inquiry. If you do not receive a reply, please contact me again! Email me for additional pictures of this wonderful hideaway. EVERY RENTER IS…
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Outdoor Dining Area
  • A/C or climate control

Details

Reviews

(6)

Great vacation location

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

We had a lovely time staying here. The highlights were the large back yard on the water with the chiki hut and the many other places to relax on the dock. And we even saw a manatee! Having the bicycles to explore the neighborhood and the double kayak to get out on the water was a bonus. The room itself was spotless and very well set up. And fishing off the dock was so much fun! Loved having the …

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$500

4 BR / 3 BA / Sleeps 8

4 Reviews

$500

Inquire

101 Palo de Oro

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

Details

Reviews

(4)

Great pool home in desirable Venetian Shores. This 4 bedroom/3 bath home is roomy and has great porches overlooking the wide, clean canal. Lovely master suite on the top floor with it's own balcony. Comfortably furnished pool home with 90 feet of excellent deep water dockage on a wide canal leading directly to Snake …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

Wonderful

Left on Jul 15, 2010 for a stay in June 2010

We have stayed at this house 2 years in a row. The house is comfortable and a great location. The area has wonderful restaurants and fishing is great. We plan on staying next year for 2 weeks.

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$300

3 BR / 2 BA / Sleeps 6

2 Reviews

$300

Inquire

107 San Remo

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

Details

Reviews

(2)

Affordable Venetian Shores canal home at the Mile Marker 86, Bay-side. Nice decor, recently updated with a private downstairs apartment. Two bedroom/one bath upstairs and a one bedroom/one bath apartment downstairs (with a complete kitchen and living room). Easy ocean or bay access via Snake Creek. CLICK HERE to view …
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Experience of a lifetime!

Left on Feb 09, 2014 for a stay in November 2013

Love the location, house was extremely well equipped, comfortable, Very accommodating to a wide range of taste and activities!

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$758

5 BR / 3 BA / Sleeps 10

17 Reviews

$758

Inquire

87445 Old Hwy

5 BR / 3 BA / Sleeps 10 | Quick view
“ Excellent ” 17 Reviews

Details

Reviews

(17)

This oceanfront home will surely get you in a Keys state of mind. Featuring five bedrooms, a pool, and an expansive private beach, its ideal for anything from a reunion of extended family or friends, to a small wedding, to a relaxing family vacation. The 4,300 square foot house will capture your attention at the …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Garage
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(17)

Great Location, house needs some nimor work

Left on Apr 07, 2011 for a stay in March 2011

Nice house, dirty carpets, screens on doors need repair, with minor cleaning and repairs this house could be great

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$300

2 BR / 3 BA / Sleeps 5

22 Reviews

$300

Book

Luxurious Anglers Reef with Boat Slip, Pool, Ocean

2 BR / 3 BA / Sleeps 5 | Quick view
“ Excellent ” 22 Reviews

Details

Reviews

(22)

House, 2 Bedrooms + Convertible Bed(s), 2.5 Baths (Sleeps 5) Islamorada home set in OceanFront gated community with swimming pool and private boat dock This charming home has 2 Bedrooms, 2.5 Bathrooms, A/C, Granite work tops, modern stainless steel appliances. Open porches and balconies, rich hard wood floors, …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(22)

Beautiful luxury and an absolute great stay in Keys! No hesitati

Left on Oct 18, 2012 for a stay in October 2012

This beautiful condo in Islamorada is pristine clean, has all the updates needed and is centrally and perfectly located if staying in the Keys! Jo (the owner) made us feel like family, gave us wonderful recommendations of who to take us snorkeling, diving, kayak rental, where to eat and even went out of her way to purchase a charcoal grill so we could cook out if we wanted to stay "home". I was …

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