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Florida Keys Rentals with Pools

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Florida Keys Rentals with Pools

772 vacation rentals

Islamorada Luxury Waterfront Condo with Boat Slip

Islamorada apartment

2 bedrooms / 3 bathrooms / sleeps 6

“Beautifully appointed, waterside condo!” This property is a beautiful, two bedroom condo, very well appointed, with everything we needed for a great stay! Islamorada is a great middle point to see the other parts of the Keys, and close to great restau

Price per night from

$215

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Steps to Duval, Old Town Charm -Grand Bahama Suite

Key West apartment

3 bedrooms / 2 bathrooms / sleeps 8

“Can't wait to return” We loved staying at the Grand Bahama suite. It was spacious, clean and centrally located just a street from all the action. We loved the courtyard and pool. I was a little concerned about parking but it worked out fine for us.

Responds fast! avg. 3 hours 11 minutes

Price per night from

$330

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1/2 Block to Duval, World of its own -Nassau Suite

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Our wedding family stayed here awesome” Fabulous. Clean roomy pool fantastic. Short walk to schooners Wharf Both inside and outside area were excellent

Responds fast! avg. 3 hours 11 minutes

Price per night from

$278

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Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 24 minutes

Price per night from

$201

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Spectacular Atlantic Ocean View Condo (MONTHLY)

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Amazing Views And A Great Condo” My wife and I stayed here on our honeymoon and were absolutely 100% pleased with the condo. I have to honestly say it was the nicest condo either of us have stayed in. The view was amazing and the patio was very tranqu

Price per night from

$330

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Relax Away - Sombrero - NEW 4BDRM W/ 40ft DOCK & PRIVATE POOL

Grassy Key house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 3 hours 41 minutes

Price per night from

$296

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All NEW Interior Oceanfront 5th Floor End Unit, Pool, WiFi, Great Ocean Views!

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 58 minutes

Price per night from

$144

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Best Location, 1/2 Block to Duval, Bimini Suite

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Perfect!” This was the perfect size suite for 4 adults, with a little pool oasis right off our doorstep, in the center of it all without the noise of Duval. Loved every second of my stay!

Responds fast! avg. 3 hours 11 minutes

Price per night from

$260

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Villa Sombrero, Marathon

Marathon house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 2 hours 55 minutes

Price per night from

$380

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Sunrise At Seaside Condo 2 bedroom 2 bath

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Exactly what we needed.” Owner responded in timely manner and was pleasant and answered all questions. The unit was easy to find and close to the airport. We worried about airport traffic noise interfering with sleep, but never heard them inside the

Responds fast! avg. 1 hour 38 minutes

Price per night from

$150

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Casa Del Sol, a Key West Vacation (Truman Annex)

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

“awesome” the condo was beautiful. very good location. 2 suggestions. the grill did not have gas . the bed that opens up to king. not so much, mattress is 2 different heights and slides if you try to sleep on it. very very uncomfortable.

Responds fast! avg. 1 hour 21 minutes

Price per night from

$229

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You Should Have Seen the One That Got Away!

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect keys hideaway” This is an amazing house, it comes with a dock, kayaks, bicycles, a fully stocked kitchen with spices and dry goods, access to the community pool and beach and great local restaurants. The owners are vey responsive and strive to

Responds fast! avg. 1 hour 26 minutes

Price per night from

$143

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Fisherman's Paradise with a 30 Ft Boat Slip

Long Key apartment

3 bedrooms / 2 bathrooms / sleeps 6

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

Responds fast! avg. 1 hour 41 minutes

Price per night from

$180

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3BR Oasis in the Keys w/ Kayaks & Bikes - Sweeping Ocean Views in Every Room!

Marathon house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$253

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Large Townhouse in Mariner's Club Resort - 3 BR/3.5 Bath

Tavernier townhouse

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 1 hour 55 minutes

Price per night from

$295

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TWICE THE CHARM

Key Largo house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$183

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PARKING,2bd/2bth,20yrd TO DUVAL,FREE OLD TOWN SHUTTLE,MAJOR ATTRACTIONS NEARBY

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 30 minutes

Price per night from

$101

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Tropical Escape

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Very comfortable and all around great place to stay.” It was very clean, comfortable and homey. The pool was great and it's very close to Key West and a beach. We really enjoyed our stay. Provided plenty of towels, pool accessories, kitchenware, etc.

Price per night from

$233

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Gorgeous Spa Villa, Marina in Florida Keys

Duck Key villa

2 bedrooms / 3 bathrooms / sleeps 6

“Loved it” Just got back from staying in this Villa. We were very happy with everything. The villa was clean & beautifully decorated & the location was perfect. I have stayed in Hawks Cays Villas twice before & this was the nicest. We will stay here

Price per night from

$176

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Family vacation rental, kayak, pool, 50” dock

Key Largo house

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 3 hours 50 minutes

Price per night from

$151

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Spacious Top Floor Condo w/ Water View!!

Marathon apartment

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$326

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FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 8 w/ 60 Feet of Dockage

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 3 minutes

Price per night from

$200

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Center of It All - Paradise Island Suite

Key West apartment

2 bedrooms / 1 bathroom / sleeps 6

“Great location in the heart of Old Town Key West, just a block off Duval..” We stayed in the Paradise Suite. Great front porch to hang out on, pool in back with pergola for lounging. Place was set up perfect, pool towels hanging by the door, bathroom

Responds fast! avg. 3 hours 11 minutes

Price per night from

$250

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Indigo Reef, 32' dock, Marathon FL

Marathon villa

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$401

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Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,503

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FLORIDA KEYS OASIS # The Corona commercial-welcome ****7 DAY MINIMUM RENTAL****

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

“Relax in Luxury” Great Location. Lots of nearby restaurants. Owners were extremely helpful in recommending attractions. A stunningly beautiful home with plenty of room for my large family to spread out. Pool was great. Swimming in warm shallo

Responds fast! avg. 1 hour 12 minutes

Price per night from

$1,002

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Houseboat Trawler MV Coconuts: Once in a Lifetime Vacation With Pool Access

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

“Nice alternatif for hotel” We were on the boat with only 2 people, so plenty of place ! We liked the marina and the boat very well. Something completely different than an hotelroom ... We had perfect weather so we used the different terraces on the b

Price per night from

$174

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Key Largo 2/2 Tropical Daze Oceanfront Condo

Key Largo apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Couldn't be better!!!” If you are looking to rest and relax, look no further.

Responds fast! avg. 54 minutes

Price per night from

$200

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PALMS 214

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$76

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Key West Condo close to the Ocean

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 24 minutes

Price per night from

$260

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Beachfront Condo with Panoramic Ocean View! Paradise in the Florida Keys!

Grassy Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 51 minutes

Price per night from

$226

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Living the Dream in the Florida Keys with Fabulous Amenities and Great Value

Key Largo apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Great place to stay” We stayed at Sally and andrew´s place for a week. When we looked for a place to stay, we wanted a place not to far of Key West and Miami, and this place was just great! There were lots of places to eat out, things to see, and Ke

Price per night from

$148

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Unit 10, Furnished Studio located 50 yards from ocean

Grassy Key apartment

/ 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 1 minutes

Price per night from

$150

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Private Beachfront Paradise

Matecumbe Key house

4 bedrooms / 3 bathrooms / sleeps 8

“Nicest rental property we have ever stayed in!!” Beautiful home on spotless white beach! Property has been updated with upscale furnishings throughout. Granite, leather furniture, redone bathrooms. Well stocked for all your vacation needs -- towels

Price per night from

$501

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Key West Florida Beachfront Condo

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

“Better than the photos” Condo is perfectly located at the beach. Well designed for easy living both inside and out. Great advise on where to visit and eat thanks

Price per night from

$301

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Kawama Yacht Club Unit 202 OCEAN AND MARINA VIEW

Key Largo condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$151

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KAWAMA TOWER- Beautiful Ocean view unit

Key Largo condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$150

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Private Heated Pool, New Boat Dock and Ready Enjoyment!

Key Colony Beach house

2 bedrooms / 1 bathroom / sleeps 4

“Keys” This house was awesome!! My family really enjoyed staying here! We plan on booking this house for next year already. It has everything you need! And it is fully renovated all throughout! We are happy we were able to find this!!

Responds fast! avg. 3 hours 24 minutes

Price per night from

$214

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