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Florida Keys Rentals with Pools

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Florida Keys Rentals with Pools

777 vacation rentals

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 27 minutes

Price per night from

$229

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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!

Price per night from

$260

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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.

Price per night from

$330

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Canal-Front 3BR w/ Private Pool, Boat Slip, Tiki Hut & Kayaks - Near Beach

Marathon house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$211

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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

$266

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WOW – waterfront, boat lift, private heated pool, walk to beach and shops!

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$201

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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 56 minutes

Price per night from

$295

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Keys Spectacular Gulf of Mexico Views

Marathon house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$229

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Amazing Ocean View Condo on the Beach!

Marathon apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Our Spirits were renewed!” Things don't happen by chance! Little did we know six months ago when we booked our vacation how much we would really, really NEED a quiet and peaceful week! This little corner of Marathon is exactly that: quiet and peace

Responds fast! avg. 2 hours 41 minutes

Price per night from

$207

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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

Price per night from

$248

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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

$135

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ADVENTURE AWAITS I - MARINER'S CLUB 606 - KEY LARGO RESORT STYLE VACATION HOME

Key Largo townhouse

4 bedrooms / 4 bathrooms / sleeps 11

Price per night from

$401

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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

Price per night from

$277

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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

$213

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FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 6 w/ 60 Feet of Dockage

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 3 minutes

Price per night from

$199

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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 48 minutes

Price per night from

$260

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Keys Cove House 4

Marathon Shores house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 13 minutes

Price per night from

$429

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New 3 bedroom luxury condos just 10 mins from 10 beaches!!

Dry Tortugas National Park apartment

3 bedrooms / 3 bathrooms / sleeps 5

Price per night from

$105

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Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect place to experience Key West” This is a lovely condo with a tropical, quiet view. Many extras are included: beach towels, bikes, and kitchen supplies. The pool area was our favorite spot, and we had coffee every morning on the balcony with cha

Responds fast! avg. 2 hours 6 minutes

Price per night from

$351

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1BR Restored Conch House w/ Pool & Deck

Key West house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$89

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75731 Overseas Highway

Matecumbe Key house

4 bedrooms / 4 bathrooms / sleeps 10

“Relaxing!” The Florida Keys are so much fun and so very casual. The house was a great way to get our family together for a week and we all enjoyed ourselves, I could have stayed for a month. The guys all went fishing and the rest of us floated in the

Price per night from

$1,045

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Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,501

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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

$219

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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 19 minutes

Price per night from

$201

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Key Largo Kampground Vacation

Key Largo house

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 56 minutes

Price per night from

$125

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Come relax in Islamorada, the tropical jewel of the Florida Keys!!

Islamorada apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 29 minutes

Price per night from

$176

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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

$394

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Bay Harbour D114

Long Key house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$322

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Brand New 3 Story Key Largo Home

Key Largo house

5 bedrooms / 3 bathrooms / sleeps 16

Price per night from

$299

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OUTSTANDING Oceanfront House with Pool and Deep water dockage!!

Marathon house

4 bedrooms / 3 bathrooms / sleeps 10

“Marathon house” A great house with an awesome ocean view! The house was very clean and the kitchen was well stocked with all we needed. We especially looked the pool area and boat dock. It accommodated our 38 ft fishing boat we brought with no problem

Responds fast! avg. 2 hours 41 minutes

Price per night from

$571

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Shelleys Rooftop Hideaway

Key West apartment

2 bedrooms / 3 bathrooms / sleeps 4

“great place to stay” Close to every thing in Key West Walking distance to all of down town stores and bar my personal favorite

Price per night from

$290

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Bayside 3BR/3BA w/ Heated Pool, Dock Access, Rooftop Terrace & Stunning View

Marathon villa

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$240

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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

Responds fast! avg. 3 hours 56 minutes

Price per night from

$176

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OASIS

Key Largo house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$251

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Canal-Front 3BR w/ Private Pool, Dock & Kayaks - Near Oceanfront Park

Marathon house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$192

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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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Duck Key Paradise

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 13 minutes

Price per night from

$329

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BUCCANEER'S DEN - 20Ft. of Waterfront w/ Dock

Key Largo house

2 bedrooms / 1 bathroom / sleeps 2

“All we expected and then some” The whole experience for us was great. From the quick response when we first asked about Rumrunners to our last day there. Nestor is great to work with, quick with any question we had, and had very good informational e

Price per night from

$81

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