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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

Details

Reviews

(7)

Wonderful

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

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

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$99

2 BR / 2 BA / Sleeps 8

1 Reviews

$99

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Newly Renovated Executive Bay Townhouse**Discounts Available**

2 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

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

(1)

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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$500

4 BR / 3 BA / Sleeps 8

9 Reviews

$500

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Private Beachfront Paradise

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 9 Reviews

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Reviews

(9)

Beautiful two story home ......four bedroom three baths.....on your private white sandy Beachfront property with large pool facing the ocean. First floor is independent with a very large one bedroom, bar with wine cooler full bath, living, dinning and new kitchen. The covered patio is huge at 60X15. The second floor…
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(9)

Great House and Great Property Owner

Left on Dec 06, 2013 for a stay in November 2013

My family and I had the pleasure of staying at this home during Thanksgiving week. Not only did the house beat our expectations, but the communication with the owner was also fantastic. She was so helpful with every inquiry we had and went well above what we expected to make sure our time in Islamorada was as well as it could be.

The house itself was extremely clean, beautiful and very …

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$77

2 BR / 2 BA / Sleeps 4

Executive Bay Club A-1 - Islamorada vacation rentals
1 / 21

$77

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Executive Bay Club A-1

2 BR / 2 BA / Sleeps 4 | Quick view

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N/A
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Dishwasher
  • Microwave
  • Toaster
  • Suitable for children - ask
  • Suitable for the elderly - ask

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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

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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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$149

2 BR / 2 BA / Sleeps 4

Moon Bay Condo A-206 - Islamorada vacation rentals
1 / 1

$149

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Moon Bay Condo A-206

2 BR / 2 BA / Sleeps 4 | Quick view

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A beautifully decorated condo located at mm 104. This unit has 2 bedrooms and 1.5 baths and its own deeded boat slip. This condo in conveniently located close to the main land. This is a perfect condo for fishermen, divers, or just a Key's getaway. Amenities include heated pool, jacuzzi, tennis courts, sauna, and game…
  • Shared outdoor pool (unheated)
  • Sauna
  • Internet Access
  • A/C or climate control
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$190

2 BR / 3 BA / Sleeps 4

1 Reviews

$190

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Futura Townhome 731

2 BR / 3 BA / Sleeps 4 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

Enjoy the spectacular view of the Florida Bay from this beautiful townhome. There are tons of things to keep you and your family busy without having to leave the Futura Condo complex. There are tennis courts and a swimming pool located on the property. Make your self at home in our home away from home. Boat dockage …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Most awesome vacation in Islamorda Florida!!

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

Futura - The price is right. The location is perfect. The townhouse is very comfortable, beautifuly decorated, with a most awesome view of Florida Bay. The marina, dock, and boat ramp are all at the same location and are well maintained. The pool, tennis courts, basketball, and volley ball court are an added bonus.
In addition, Freewheeler Realty has been providing our vacation services for over …

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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

Reviews

(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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$643

4 BR / 3 BA / Sleeps 8

1 Reviews

$643

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Aguazul

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

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Reviews

(1)

Village Permit #VR-09-82 You can not rent this property for less than one week. Ahhhh...Ocean Front...Pool...Dockage...It's all hear at Aguazul. Aguazul is located at Mile Marker 89, in beautiful Islamorada. This gorgeous four bedroom,three bath home will sleep 8 people very comfortably. Aguazul has everything you …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

The perfect getaway

Left on Sep 26, 2011 for a stay in August 2011

My family had a fantastic vacation. This home is located really close to some great restaurants. It was so nice to sit back and relax all day while the kids played in the ocean and pool.

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$100

2 BR / 2 BA / Sleeps 6

2 Reviews

$100

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Summer Sea #418 - 28 Night Minimum

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

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Reviews

(2)

This 2 bedroom, 2 bathroom condo located directly on the Florida Bay is the perfect sunny getaway! Situation with perfect views of the community pool, community marina, and open bay, you'll enjoy coffee in the morning while watching the boaters head out for their perfect catch and enjoy a sunset cocktail in the …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Smoking allowed - ask
  • Suitable for children - ask
  • 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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$214

2 BR / 3 BA / Sleeps 6

1 / 24

$214

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LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

2 BR / 3 BA / Sleeps 6 | Quick view

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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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$643

4 BR / 3 BA / Sleeps 8

1 / 1

$643

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50 Schooner Bay Rd - Aguazul

4 BR / 3 BA / Sleeps 8 | Quick view

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How about sipping coffee and watching the sun come up as you fish off the end of your very own 300 foot pier? Sounds good, right? Well, that's just one reason to stage your upcoming vacation at this lovely, hacienda-style home on a quaint and private oceanfront street in Islamorada. CLICK HERE to view photos on a …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$150

3 BR / 2 BA / Sleeps 6

1 / 1

$150

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127 Tequesta - 28 Night Minimum

3 BR / 2 BA / Sleeps 6 | Quick view

Details

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

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$140

1 BR / 1 BA / Sleeps 4

1 / 11

$140

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Seagulls Condominiums, Enjoy the Florida Keys!

1 BR / 1 BA / Sleeps 4 | Quick view

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Come enjoy our home away from home. Perfect for a couples retreat. Enjoy your own fully equipped condo. Sip coffee on the balcony and watch the beautiful sunrise. Read one of our Jimmy Buffett books and dream of running away for a life on sea. Once this salt air gets in you you will never want to go home. Please…
  • Waterfront
  • Sauna
  • A/C or climate control
  • Central heating
  • Balcony or terrace

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$500

4 BR / 3 BA / Sleeps 8

4 Reviews

$500

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101 Palo de Oro

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

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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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$243

3 BR / 2 BA / Sleeps 6

2 Reviews

$243

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Islamorada PARADISE FOUND 3 bedroom/2 bath

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

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Reviews

(2)

BEAUTIFUL NEWLY REMODELED 3 BEDROOM, 2 FULL BATHROOM VACATION RENTAL IS LOCATED IN THE EXECUTIVE BAY CLUB. BREATHTAKING BAY VIEW FROM YOUR OWN BACK YARD! UNIT HAS BRAND NEW CUTOME KITCHEN CABINETS WITH GRANITE COUNTER TOPS. ALL STAINLESS STEEL APPLIANCES, DOUBLE DOOR REFRIGERATOR, DISHWASHER, GLASS STOVE COUNTER …
  • Ocean or water views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children

Details

Reviews

(2)

Beautiful, relaxing and comfortable!

Left on Feb 23, 2015 for a stay in December 2014

When we first contacted the owner regarding the rental, she responded immediately and was very nice and helpful. The unit was impeccable when we arrived and the location in the complex was excellent! We were right in front of the pool, and the beach area was very close. One of my favorite things to do during our stay was to sit out in the terrace of the unit and relax while looking at the ocean. …

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$190

2 BR / 3 BA / Sleeps 4

2 Reviews

$190

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Futura Townhome 708

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

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Reviews

(2)

This unit's kitchen, bathrooms, windows, and doors received a facelift in January 2014! Enjoy the spectacular view of the Florida Bay from either one of the TWO balconies in this 2 story townhome, located off the master bedroom or the living room. Amenities include Wi-Fi, flat panel TV's in the living room and master …
  • Waterfront
  • Shared outdoor pool (unheated)
  • Grill
  • Dishwasher
  • Microwave
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

i need of update and repiar

Left on Mar 11, 2011 for a stay in February 2011

In need of repair pant and up date . They ants all over contertops paint was peeling from walls and trim.

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$215

3 BR / 2 BA / Sleeps 6

15 Reviews

$215

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Windy Cove Townhome #1

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 15 Reviews

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Reviews

(15)

Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak up the sun on the …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Television
  • Telephone
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(15)

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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$243

2 BR / 3 BA / Sleeps 6

1 / 25

$243

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Anglers Reef Islamorada Florida Sleeps 6

2 BR / 3 BA / Sleeps 6 | Quick view

Details

2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This magnificent oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on the 500' of …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

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$715

4 BR / 3 BA / Sleeps 10

1 / 8

$715

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82754 Overseas Highway

4 BR / 3 BA / Sleeps 10 | Quick view

Details

OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering 5 bedrooms and 3 full baths on 2 living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comfortably. Spacious fully equiped kitchen with the …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$397

2 BR / 3 BA / Sleeps 5

1 / 14

$397

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Islamorada getaway home with private boat dock.

2 BR / 3 BA / Sleeps 5 | Quick view

Details

This property is a single family home with a boat dock included in the price. Not a condo. Note: we only offer 7 day minimum stays with 4PM Saturday check ins and 10 AM checkouts. Maximum number of guests is 5. No pets, No smoking and maximum guests is strictly enforced. Rates start at $2,775 per week plus tax and …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Suitable for children

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$300

2 BR / 2 BA / Sleeps 6

1 Reviews

$300

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Islamorada Florida Keys Beautiful 2B 2B Townhouse

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

Details

Reviews

(1)

We also have monthly and 3 day weekend rates! 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 …
  • Waterfront
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children

Details

Reviews

(1)

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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$179

1 BR / 1 BA / Sleeps 2

1 / 4

$179

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CASA THORN

1 BR / 1 BA / Sleeps 2 | Quick view

Details

Enter through a private garden with a tropical atmosphere to a quiet and secluded room with a queen size bed and a private bath. The room is completely private and features a coffee maker, microwave, refrigerator, TV and free WiFi. Full breakfast. LOCATED IN A QUIET,SECLUDED , TROPICAL SETTING YET MINUTES TO FISHING…
  • Shared outdoor pool (unheated)
  • Wireless Internet
  • A/C or climate control
  • Balcony or terrace
  • Parking
  • Pet friendly
  • Suitable for children

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$97

2 BR / 2 BA / Sleeps 6

1 / 26

$97

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THE PALMS 405 - 93

2 BR / 2 BA / Sleeps 6 | Quick view

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Minimum Rental: 1 Month A Diamond! Be among the first to rent this gorgeous two bedroom condo. It has been completely renovated from floor to ceiling. The floors have been replaced with tile and the old popcorn ceilings are gone. You'll adore the comfortable living room furnishings and the flat screen TV, not …
  • 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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$140

3 BR / 2 BA / Sleeps 6

1 / 26

$140

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OCEAN BREEZE

3 BR / 2 BA / Sleeps 6 | Quick view

Details

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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$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

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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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$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

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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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$110

2 BR / 2 BA / Sleeps 4

1 / 20

$110

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BEACON REEF 314

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Minimum Rental: 1 Month Beacon Reef is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yourself relaxing on your own private balcony …
  • 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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$123

3 BR / 2 BA / Sleeps 6

1 / 21

$123

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THE PALMS 316

3 BR / 2 BA / Sleeps 6 | Quick view

Details

MINIMUM STAY: 29 DAYS Enjoy unobstructed and panoramic views of the Atlantic Ocean from your own private balcony! This 3 bedroom/2 bath condo unit features direct ocean views from the living room, balcony and two of the three bedrooms. Tropical furnishings create a warm and inviting atmosphere. You'll really…
  • 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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$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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$133

2 BR / 2 BA / Sleeps 4

1 / 17

$133

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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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$167

2 BR / 2 BA / Sleeps 4

1 / 24

$167

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OCEAN HARBOUR K4

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Minimum Rental: 1 Month New on the rental market. This is your opportunity to secure your winter getaway at a luxurious oceanfront condo in one of Islamorada's most prestigious condominium communities. Ocean front dockage is available for boats up to 28' in length (separate rental); heated free-form swimming pool, …
  • 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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$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
  • Patio
  • 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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$70

2 BR / 2 BA / Sleeps 4

1 / 18

$70

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THE PALMS 214

2 BR / 2 BA / Sleeps 4 | Quick view

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Minimum Rental: 1 Month Gorgeous 2 bedroom, 2 bath condo. This is a gated complex located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master suite and the balcony. Wake up every morning, open the curtains and view a panorama of the Atlantic Ocean directly in front of you…
  • 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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$70

2 BR / 2 BA / Sleeps 6

1 / 16

$70

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THE PALMS 301

2 BR / 2 BA / Sleeps 6 | Quick view

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Minimum Rental: 1 Month This exceptional condo has been impeccably maintained and is located in one of the finest condo complexes in Islamorada. It features an updated kitchen, remodeled baths and is comfortably furnished. This unit is ready for your arrival. Be sure to look at the Visual Tour to see just how …
  • 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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$133

2 BR / 2 BA / Sleeps 4

1 / 18

$133

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BEACON REEF 211

2 BR / 2 BA / Sleeps 4 | Quick view

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Minimum Rental: 1 Month This is a very special unit in a premier condominium complex located directly on the Atlantic Ocean and in the heart of Islamorada. This unit provides spectacular ocean views. It is one of the few units that offer spiral stairs to the ground level directly from your private balcony. The …
  • 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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$77

2 BR / 2 BA / Sleeps 5

1 / 21

$77

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THE PALMS 314

2 BR / 2 BA / Sleeps 5 | Quick view

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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

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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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$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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$67

2 BR / 2 BA / Sleeps 4

1 / 14

$67

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THE PALMS 408

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Minimum Rental: 1 Month Comfortably furnished and ready for you. Conveniently located just steps from a full service marina and 2 highly acclaimed restaurants. Watch the sun rise over the ocean as fishing boats leave on their daily charters, or watch the spectacular sunsets over the bay. Exercise in the men's or…
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Patio
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$80

2 BR / 2 BA / Sleeps 4

1 / 20

$80

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THE PALMS 403

2 BR / 2 BA / Sleeps 4 | Quick view

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Minimum Rental: 1 Month This exceptional 2 bedroom and 2 bath condo is located in one of the most popular Islamorada condo complexes - The Palms. The balcony is large enough to dine or recline and offers fabulous open water ocean views. Watching the sunrise over the Atlantic Ocean as you sip your morning …
  • 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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$172

2 BR / 2 BA / Sleeps 4

3 Reviews

$172

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Sea Gulls Condo - Unit 406

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

Details

Reviews

(3)

This newly remodeled & renovated (in 2012), two bedroom, Sea Gulls Condo unit, located on the oceanside of Plantation Key at Mile Marker 90, has an awesome view! Unit is comfortably and stylishly furnished, has TVs in the living room, two queen beds and a sleeper sofa. The Sea Gulls community features a fish cleaning …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Sauna
  • Internet Access
  • Suitable for children - ask
  • 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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$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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$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

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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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$215

3 BR / 2 BA / Sleeps 6

3 Reviews

$215

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Windy Cove Townhome #3

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

Details

Reviews

(3)

Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak up the sun on the …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Central heating
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Fun in the Pool, comfort in the Condo

Left on Apr 10, 2014 for a stay in March 2014

Six of us were in Islamorada for a friend's wedding at a nearby rental property. The location was perfect for us, and convenient for getting on and off the busy highway. The condo was comfortable and as advertised. We had everything we needed to cook in the kitchen and plenty of bath towels. The view from the deck was spectacular. We spent time in the pool every day. It was a short walk to …

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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 - ask
  • Suitable for the elderly - ask

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$472

3 BR / 3 BA / Sleeps 6

1 Reviews

$472

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Maison Matecumbe 304

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

Details

Reviews

(1)

This three bedroom, three bathroom condominium sits on a lushly landscaped property, offering the Florida Keys you've always imagined. Enjoy beautiful oceanfront vistas from one of two balconies. Take a dip in the spacious pool that sits right at the foot of the condo staircase. Or journey a few yards further to the …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Porch
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Relaxing in Islamorada

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

Everything was beautiful. Very nice property. Private but very close to fishing charters.

Toaster did not work and upstairs a/C quit working the night before we left. Other than that the condo was great.

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$275

3 BR / 2 BA / Sleeps 6

3 Reviews

$275

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Islamorada “The Getaway” Relax in Florida Keys!

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

Details

Reviews

(3)

Thank you for considering Our home in the Florida Keys!... Our slice of Paradise! Stay at a Luxury Townhome at Executive Bay Club (Islamorada , Florida ) The Executive Bay Club is located in Islamorada which is best known for it's crystal blue water where you can enjoy sport fishing, snorkeling, diving and boating…
  • Waterfront
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(3)

The Keys at its Best

Left on Mar 26, 2014 for a stay in March 2014

We stayed at "The Getaway" for spring break...a break from it all. This is place was wonderful! First, Luis and Paula were wonderful from initial inquiries, to providing suggestions for things to do and places to go, through the end of our stay and follow up. They were available by phone and email if we had a question. The home was wonderfully decorated and clean! two sets of bunk beds and a…

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$1,715

10 BR / 10 BA / Sleeps 28

12 Reviews

$1,715

Inquire

Alligator Reef Luxury Estate

10 BR / 10 BA / Sleeps 28 | Quick view
“ Excellent ” 12 Reviews

Details

Reviews

(12)

Got a large group that wants to "get away from it all"? Or do you need lots of space for a family reunion or wedding? This is the perfect solution! Terrific location, beautiful view, two private pools for you to enjoy... And since it's 4 separate homes, you aren't right on top of each other. Wide decks let you enjoy …
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(12)

Island Perfection

Left on Jul 01, 2010 for a stay in May 2010

Perfect house for a island getaway. Hammocks, wildlife, marinelife, pool, kayaks, near "the infamous islamorada sandbar", ping pong table, boat rentals nearby, the place couldn't be better for kicking back soaking up everything that makes the Florida Keys special.

Real friendly and easy to deal with reservation systems and staff. A++ all the way. We will use Freewheeler again and again.

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$215

3 BR / 2 BA / Sleeps 6

1 Reviews

$215

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Islamorada bay front condo with deep water 36ft boat slip

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

Details

Reviews

(1)

Beautiful bayside condo, 3bedrooms 2baths, sleeps 6 comfortably, new sealy beds in all rooms with cable and wifi. Newly furnished and clean. Comes with 36 foot boat slip in the marina. There is a boat ramp on the property along with a brand new pool. Deep water dockage and deep channel to bay, minutes to snake …
  • Waterfront
  • Shared outdoor pool (unheated)
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(1)

Good rental for a boater's vacation

Left on Jun 15, 2014 for a stay in June 2014

We spent a full week at this Futura Yacht Club rental, which we enjoyed very much. Here are the pro's and con's:

Pro:

Boat slip accommodated our 29 foot boat well

Fresh water wash downs at each slip

Well lit dock

BBQ facilities by dock

Tiki hut/beach chairs on community beach area with nice gulf view/sunsets!!!

Easy access to ocean via snake creek

Large clean pool with lots of seating …

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