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$100

2 BR / 2 BA / Sleeps 4

2 Reviews

$100

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Summer Sea Condominium Complex

Islamorada condo
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent2 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 offer …
  • 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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$215

3 BR / 2 BA / Sleeps 6

16 Reviews

$215

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Windy Cove Townhomes

Islamorada condo
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent16 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 have …
  • 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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$110

2 BR / 1 BA / Sleeps 4

75651 Overseas Hwy Islamorada Fla Keys Oceanfront - Islamorada vacation rentals
1 / 17

$110

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75651 Overseas Hwy Islamorada Fla Keys Oceanfront

Matecumbe Key condo
2 BR / 1 BA / Sleeps 4 | Quick view

Details

Directly on your private oceanfront beach. Ocean views from every room of your two bedroom one bath Keys style duplex villa. You will experience the true 'old Keys' charm of bird watching on the wraparound deck to fishing on the beach...or perhaps just relaxing on the sand. With over a half acre of tropical landscape…
  • Private Beach
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$107

2 BR / 2 BA / Sleeps 6

11 Reviews

$107

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Islamorada Tropical Escape! Clean, Affordable & Li

Islamorada condo
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent11 Reviews

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Reviews

(11)

Escape from the world in this beautiful island paradise.Plenty of room to spread out in a two bedroom condo. Relax by the heated pool overlooking the turqoise bay; fish from the dock, snorkel in the protected cove. Kids can play in the game room or playground. Enjoy the clear, turquoise waters, breathtaking views, …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(11)

Great vacation!

Left on Jan 17, 2012 for a stay in January 2012

The condo was very convienient, well equipped, comfortable and clean. With a four year old and a five month old, we had plenty of room, pack and play available, and some Disney/Sprout for the rainy afternoon was great! Had lots to do in the area and had a great time!

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$70

2 BR / 2 BA / Sleeps 6

THE PALMS 301 - Islamorada vacation rentals
1 / 16

$70

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THE PALMS 301

Islamorada condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

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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$358

4 BR / 3 BA / Sleeps 8

Blue Harbour - Islamorada vacation rentals
1 / 12

$358

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Blue Harbour

Islamorada house
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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$429

5 BR / 4 BA / Sleeps 10

8 Reviews

$429

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140 Atlantic Lane

Islamorada house
5 BR / 4 BA / Sleeps 10 | Quick view
Excellent8 Reviews

Details

Reviews

(8)

Amazing ocean views can be enjoyed from this beautiful stilt home with seperate mother-in-law cottage. You'll fall in love with this little piece of Heaven. Enjoy fishing, diving, and catching lobster with all the comforts of home. Best ocean views in town! Interior photos are available! Mile Marker 76.5, Oceanside. …
  • Waterfront
  • Ocean or water views
  • A/C or climate control
  • Grill
  • Dishwasher
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(8)

Summer vacation 2010

Left on Sep 13, 2010 for a stay in August 2010

Overall nice place, kitchen items were not very organized, and place could use a deep cleaning

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$500

3 BR / 3 BA / Sleeps 8

23 Reviews

Details

Reviews

(23)

Private heated pool vacation home located on deep canal with immediate access to ocean and bay. Mile Marker 86 in prestigious Venetian Shores. Pet friendly Vacation Rental License. No VR-001 106 San Remo Drive, Islamorada, Florida, 33036 Please email VenetianTropics@aol.com for the application. Weekly vacation rental…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(23)

Favorite trip ever

Left on Mar 01, 2011 for a stay in April 2007

This was the best vacation we ever had, and it had much to do with this rental ! We drove from Maryland and pulled our boat. It was great being able to put it in the water and have it right behind where we stayed. The home was beautiful, clean and well equipped for vacationing !!! The kids loved the pool !!! We will Definetly be back !!!

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$300

3 BR / 2 BA / Sleeps 6

2 Reviews

$300

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107 San Remo

Islamorada house
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent2 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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$858

5 BR / 6 BA / Sleeps 10

1 / 22

$858

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Southern Comfort

Islamorada house
5 BR / 6 BA / Sleeps 10 | Quick view

Details

Village Permit # VR-204 You can not rent this property for less than one week. Sit back, relax, a light breeze, gaze the blue waters of the Atlantic Ocean….and be lost. Southern Comfort is the perfect vacation home in the Florida Keys, located at MM 77. This very private Estate sits on 3+ acres offering 5 bedrooms…
  • 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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$643

4 BR / 3 BA / Sleeps 8

1 / 34

$643

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50 Schooner Bay Rd - Aguazul

Islamorada house
4 BR / 3 BA / Sleeps 8 | Quick view

Details

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
  • 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

Islamorada house
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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$117

2 BR / 3 BA / Sleeps 4

2 Reviews

$117

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

Matecumbe Key house
2 BR / 3 BA / Sleeps 4 | Quick view
Excellent2 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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$140

3 BR / 2 BA / Sleeps 6

1 / 26

$140

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OCEAN BREEZE

Islamorada house
3 BR / 2 BA / Sleeps 6 | Quick view

Details

MINIMUM STAY 29 DAYS. BEAUTIFUL CANAL FRONT STILT HOME WITH HEATED POOL - For the guest who expects perfection this is it. This home was completely remodeled in 2013. There is 936 square feet of living area on the main level with 2 bedrooms, a full bath and an open living area. On the ground level there is a …
  • 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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$2,000

0 BR / 1 BA / Sleeps 4

6 Reviews

$2,000

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Studio condo in Islamorada

Islamorada condo
0 BR / 1 BA / Sleeps 4 | Quick view
Very Good6 Reviews

Details

Reviews

(6)

This is a tastefully decorated, fully air-conditioned studio unit with a full bathroom, completely tiled. It offers a queen-sized Murphy bed that can be easily stowed away during the day. On the fully screened and enclosed balcony you will find a glass-top table with two chairs, ceiling fan, TV, single-sized sleeper …
  • Sauna
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(6)

magic

Left on Mar 17, 2011 for a stay in January 2011

spent 3 weeks in condo islamorada , we rented from victoria furdui , from start to finish everything was terriffic we had a ball , loved every second of our holiday . only problem was we could not bring sunshine back to ireland.
the condo was very clean , neat , no problems at all . the location is very good easy to get to sea side and shopping in miami . highly recommend this place . jim julie …

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$200

2 BR / 1 BA / Sleeps 4

2 Reviews

$200

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83261 Old Highway

Islamorada house
2 BR / 1 BA / Sleeps 4 | Quick view
Excellent2 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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$286

3 BR / 3 BA / Sleeps 6

4 Reviews

$286

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130 Bayview Isle Dr

Islamorada house
3 BR / 3 BA / Sleeps 6 | Quick view
Excellent4 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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$640

5 BR / 4 BA / Sleeps 9

4 Reviews

$640

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Islamorada Oceanfront Executive Rental

Islamorada house
5 BR / 4 BA / Sleeps 9 | Quick view
Excellent4 Reviews

Details

Reviews

(4)

Millionaire's Row! Beautiful home with private heated swimming pool directly on the ocean in Islamorada. This home offers excellent views of the ocean from many rooms. 5 bedroom, 4 bath owners home is beautifully furnished with ocean views from patio, living room (upper and lower), and dining room and ready to move …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(4)

location

Left on Feb 08, 2012 for a stay in May 2011

This is a very comfortable home in the best location in the keys. Great pool and fantastic pier with good fishing.Plenty of good restaraunts and bars nearby. Very good service from rental agency, any problems (minor) we have had have been taken care of promplty. We have rented this home for 6 years in a row and going back in May.

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$159

1 BR / 1 BA / Sleeps 4

18 Reviews

$159

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Sues Promise - New on the Market

Matecumbe Key villa
1 BR / 1 BA / Sleeps 4 | Quick view
Excellent18 Reviews

Details

Reviews

(18)

Two villas conveniently located at MM 75.5 with bay or garden views you are just minutes from boat ramps, great restaurants, beaches, shopping, fishing, snorkeling etc. Key West is only 75 miles away- an easy day trip! Private beach and boat basin. Bring your boat. Fish, swim, kayak or snorkel from the dock. Queen …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(18)

Wonderful paradise get away

Left on Apr 07, 2012 for a stay in July 2011

Are family of four stayed last summer. We enjoyed the comfort of the rental, the beauty of the dock and gardin, the kindness of Charles the owner and the ideal location in the Keys. It's just a perfect vacation spot for anyone who loves nature.

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$300

2 BR / 3 BA / Sleeps 5

22 Reviews

$300

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Luxurious Anglers Reef with Boat Slip, Pool, Ocean

Islamorada house
2 BR / 3 BA / Sleeps 5 | Quick view
Excellent22 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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$143

2 BR / 0 BA / Sleeps 4

3 Reviews

$143

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Sea Gulls Condominium Complex

Islamorada condo
2 BR / Sleeps 4 | Quick view
Excellent3 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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$329

3 BR / 3 BA / Sleeps 6

6 Reviews

$329

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138 Bayview Isle

Islamorada house
3 BR / 3 BA / Sleeps 6 | Quick view
Very Good6 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
  • 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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$354

2 BR / 3 BA / Sleeps 5

1 / 19

$354

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131 Anglers Way. Islamorada Vacation Home w/Dock

Islamorada house
2 BR / 3 BA / Sleeps 5 | Quick view

Details

This property is a single family home, 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 by onsite securty. Rates start at $2,475 per week plus 12.5% tax and cleaning fee …
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Suitable for children

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$236

3 BR / 2 BA / Sleeps 6

2 Reviews

$236

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155 Azalea Street

Islamorada house
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent2 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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$100

2 BR / 2 BA / Sleeps 4

1 Reviews

$100

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VILLA RIOLO

Islamorada house
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent1 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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$329

3 BR / 3 BA / Sleeps 6

7 Reviews

$329

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137 Leserra Lane

Islamorada house
3 BR / 3 BA / Sleeps 6 | Quick view
Excellent7 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 …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Grill
  • 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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$258

2 BR / 2 BA / Sleeps 6

3 Reviews

$258

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Florida Keys Beautiful 2B 2B Townhouse

Islamorada villa
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent3 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
  • Internet Access
  • 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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$400

4 BR / 5 BA / Sleeps 8

2 Reviews

$400

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74920 Overseas Hwy

Islamorada house
4 BR / 5 BA / Sleeps 8 | Quick view
Excellent2 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
  • 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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$500

4 BR / 2 BA / Sleeps 10

1 Reviews

$500

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Main House

Islamorada house
4 BR / 2 BA / Sleeps 10 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

This large 4 bedroom house sits jst 10 feet from a 116 foot dock. You are right around the corner from 4 bridges in a row where yo can get to the Ocean or Bay within a few minutes.
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(1)

Great Spot for a big group!

Left on Aug 26, 2014 for a stay in August 2014

We had a great stay! Ended up renting both houses for a weekend stay. Had 15 people and 4 boats. We had a great weekend, Helen and her son Rob were very accommodating and quickly fixed a minor issue with the air conditioning that we had on arrival. Will be back to Su Casa for sure!

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$758

5 BR / 3 BA / Sleeps 10

17 Reviews

$758

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87445 Old Hwy

Islamorada house
5 BR / 3 BA / Sleeps 10 | Quick view
Excellent17 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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$147

2 BR / 2 BA / Sleeps 4

1 / 17

$147

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BEACON REEF 222

Islamorada condo
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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$150

3 BR / 3 BA / Sleeps 6

4 Reviews

$150

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200 Plantation Shores Drive

Islamorada house
3 BR / 3 BA / Sleeps 6 | Quick view
Excellent4 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
  • 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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$200

3 BR / 2 BA / Sleeps 8

1 Reviews

$200

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Beautiful Captain's Cove

Islamorada villa
3 BR / 2 BA / Sleeps 8 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

Relax and enjoy a peaceful getaway in beautiful Islamorada, Florida. This unique home is nestled on a bay overlooking the ocean. We are located on Lower Matecumbe Key just a few miles south of the hustle and bustle of downtown Islamorada. This is a spacious three bedroom with vaulted ceilings, a loft in the master …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

Great property!

Left on Nov 18, 2014 for a stay in November 2014

We stayed at Captains Cove again for our annual fishing weekend. Cindy, the new owner, has made several updates to the house, deck and dock which enhanced the property since our 2013 visit. It is clean, comfortable and well furnished. We thoroughly enjoyed ourselves and the location couldn't be better! Thank you Cindy for being so responsive! We will be back again soon!

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$123

3 BR / 2 BA / Sleeps 6

1 / 21

$123

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THE PALMS 316

Islamorada condo
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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$250

2 BR / 2 BA / Sleeps 4

1 / 20

$250

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Oceanfrontparadise: 209

Islamorada condo
2 BR / 2 BA / Sleeps 4 | Quick view

Details

Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the "Sport Fishing Capital of the World". Our ocean contains the world's most sought-after gamefish including tuna, dolphin, Marlin, permit, tarpon and bonefish. In addition to fishing, Islamorada is a favorite of divers too. Our …
  • Balcony or terrace
  • Linens Provided
  • Towels Provided
  • Freezer
  • Microwave
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$145

1 BR / 1 BA / Sleeps 4

1 / 23

$145

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Heron House - Keys style Cottage

Islamorada cottage
1 BR / 1 BA / Sleeps 4 | Quick view

Details

Come watch the sunrise over the ocean while sipping coffee on the patio. If you love to fish, play in the water, or just relax this is the destination for you. Situated on the old highway ocean side in a small quiet RV Park. The park has a small marina, and a small sand beach with swimming. The roads in the park are …
  • Waterfront
  • Ocean or water views
  • Outdoor Dining Area
  • A/C or climate control
  • Porch
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$500

4 BR / 3 BA / Sleeps 8

4 Reviews

$500

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101 Palo de Oro

Islamorada house
4 BR / 3 BA / Sleeps 8 | Quick view
Excellent4 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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$97

2 BR / 2 BA / Sleeps 6

1 / 26

$97

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THE PALMS 405 - 93

Islamorada condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

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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$133

2 BR / 2 BA / Sleeps 4

1 / 18

$133

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BEACON REEF 211

Islamorada condo
2 BR / 2 BA / Sleeps 4 | Quick view

Details

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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$358

2 BR / 2 BA / Sleeps 6

1 Reviews

$358

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LITTLE BAY - Cottage

Islamorada villa
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

Minimum Rental: 7 Nights Cottage - This is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, dining area, sitting area and a full bath. To the right is …
  • Ocean or water views
  • Internet Access
  • Parking
  • Grill
  • Refrigerator
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

A place where memories are made.....

Left on May 28, 2013 for a stay in May 2013

The pictures really don't do this place justice, there are so many comforts that it feels more like a home. It is in a great location and since it is gated, it was safe enough for my 9 year old twins to go exploring on their own. It truly has something for everyone. We cooked, laid out, watched the sunset, even took a dip in the bay. It was really lovely. We will definitely be returning.

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$110

2 BR / 2 BA / Sleeps 4

1 / 20

$110

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BEACON REEF 314

Islamorada condo
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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$77

2 BR / 2 BA / Sleeps 4

1 / 14

$77

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THE PALMS 402

Islamorada condo
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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$107

2 BR / 2 BA / Sleeps 4

1 / 23

$107

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BEACON REEF 501

Islamorada condo
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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$217

3 BR / 2 BA / Sleeps 6

1 Reviews

$217

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MY PARADISE

Islamorada house
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

Minimum Rental: 1 Month Oceanfront - Beach - Protected Dock and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The Florida Keys. From the moment you arrive, you'll know …
  • Ocean or water views
  • Internet Access
  • Balcony or terrace
  • Parking
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

My Paradise from architect's perspective

Left on Jan 23, 2013 for a stay in April 2012

My wife and I spend a month at My Paradise and, as an architect, there are certain aspects that bear mention. First, if the weather is mild, you can open the wall of folding glass doors and unite the main interior room (dining, den and kitchen) with the oversize teak deck. The deck itself is a marvel. A covered sitting area gets you out of the sun, with six teak sun loungers for warming up and …

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$358

2 BR / 2 BA / Sleeps 6

3 Reviews

$358

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LITTLE BAY - Upper Duplex

Islamorada villa
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent3 Reviews

Details

Reviews

(3)

Minimum Rental: 7 Nights Upper Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each unit sleeps up to 6 people - …
  • Ocean or water views
  • Internet Access
  • Patio
  • Parking
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(3)

Iguanas, sunshine and the sea in your backyard.......

Left on Nov 05, 2012 for a stay in October 2012

We found Little Bay after our previously planned accomodation had been damaged in a fire so Andi & Katy at Keys Holiday Rentals literally saved us from camping on the beach! The apartment couldn't have been nicer, 2 bed, 2 bath with the second bedroom having twin beds so was perfect for the children (6 & 12). The apartment was well laid out with a HUGE deck overlooking the garden (iguanas!) and …

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$77

2 BR / 2 BA / Sleeps 5

1 Reviews

$77

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THE PALMS 314

Islamorada condo
2 BR / 2 BA / Sleeps 5 | Quick view
Excellent1 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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$63

2 BR / 2 BA / Sleeps 4

1 / 15

$63

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THE PALMS 506

Islamorada condo
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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$1,715

10 BR / 10 BA / Sleeps 20

13 Reviews

$1,715

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Alligator Reef Luxury Estate

Islamorada house
10 BR / 10 BA / Sleeps 20 | Quick view
Excellent13 Reviews

Details

Reviews

(13)

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
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(13)

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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$911

5 BR / 6 BA / Sleeps 10

1 / 1

$911

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Little Bay Compound

Islamorada house
5 BR / 6 BA / Sleeps 10 | Quick view

Details

Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units, accommodating a total of 18 people. The Upper Duplex & realty.com/display-rental-…
  • 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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$3,000

2 BR / 2 BA / Sleeps 4

3 Reviews

$3,000

Inquire

2-bed,1.5-bath Condos On The Bay, Islamorada

Islamorada condo
2 BR / 2 BA / Sleeps 4 | Quick view
Average3 Reviews

Details

Reviews

(3)

Complex Amenities - MM 88.5 - Building has five floors - Large swimming pool & children's pool - Exercise room with sauna - Laundry room on each floor - Billiard and Ping-Pong room - Adult party lounge - Cookout facilities - Direct access to Florida Bay and then ocean - Minutes from Islamorada, “sport fishing …
  • Waterfront
  • Ocean or water views
  • Sauna
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(3)

Beautiful Vacation Spot- Great for families!

Left on Apr 18, 2013 for a stay in April 2013

The condo in Islamorada was clean, updated, and nicely furnished, perfect for our family of 4. The kitchen is updated with granite counters & stainless steel appliances. The view from the living area in the condo is simply gorgeous-crystal clear water. There is a cozy little deck for drinking coffee in the morning and watching sunsets in the evening. The master bedroom has a king size bed, …

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