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Florida Keys Rentals with Pools

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559 house rentals in Florida Keys with pools

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 peaceful. The condo is very comfortably furnished, very clean, and the view is - well, I don't think there is a 'better' view anywhere! It's picture perfect - even to the gorgeous green iguana on the palm tree! (but you have to look quick - they move fast!). We had our son, daughter in law and two little grandkids with us...it was perfect! Sunrise with coffee by the pool, under the Chickee or on the patio...awesome! Lots to do for families or singles very close by...yup...you really can even have pizza delivered if you don't want delicious, fresh seafood!..and wow! are there some awesome spots for that!! Communication with the owners is impeccable...could NOT be better. These are the folks with whom you love to do business!! Thanks so much, Todd and Jamie!

Responds fast! avg. 2 hours 48 minutes

Match: Swimming pool

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Price per night from

$278

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. 2 hours 3 minutes

Match: Swimming pool

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Price per night from

$245

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$311

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

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$288

Duck Key Paradise

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 1 hour 51 minutes

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Price per night from

$601

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$1,719

Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach

Key West townhouse

2 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$572

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 chairs for all 6 of us. My husband enjoyed watching March Madness on the large T.V. Kathy did a fantastic job with all communications and provided great tourist tips. We would definitely stay here again!

Responds fast! avg. 2 hours 55 minutes

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Price per night from

$487

75731 Overseas Highway

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

“Vacation of a lifetime!” I can't say enough good things about this home. It was beautiful, clean, and peaceful. The only thing that might be considered a down side is that all of the bedrooms are located upstairs, but that was not a problem for us. Brandi at Freewheeler Realestate was wonderful. She was prompt with answers to questions, friendly and professional. The home-owner obviously wants to see to it that the people staying in their home are well taken care of. Everything was great all the way down to the fluffy beach towels. We will definitely look at staying at this home again.

Match: Swimming pool

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Price per night from

$1,227

Pools, Jacuzzis, Rec Room, Gym, 24/7 security! Stay at Mariner's Club 606!!

Key Largo townhouse

4 bedrooms / 4 bathrooms / sleeps 10

Match: Swimming pool

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Price per night from

$572

Villa Sombrero, Marathon

Marathon house

5 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$658

Bayside Home w/ Heated Pool, Rooftop Terrace & Stunning View

Marathon villa

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$283

Top floor, two bedroom,two bath condo with private balcony,close to the Ocean

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 14 minutes

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Price per night from

$430

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 57 minutes

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Price per night from

$164

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

Islamorada apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 25 minutes

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Price per night from

$200

Key Largo Kampground Vacation

Key Largo house

1 bedroom / 1 bathroom / sleeps 3

“Great location and pleasantly surprised!” Romberto's Camprground vacation was definitely more than i expected. There was ample room for my husband and I, the folks were nice and the area was quiet and clean. The marina was convenient (small boats only). There was a small leak in the bathroom in the overhead skylight but it was almost negligible unless it was pouring. we will definitely be back.

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Price per night from

$144

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.... No complaints.

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Price per night from

$270

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, beach chairs, beach toys, kitchen full of everything you need, 2 grills. Outside patio was amazing for our meals, sunrises and after dinner activities. The backyard was the beach filled with palm trees for natural shade. Hammock and volleyball court, beautiful pool with waterfall, tables and chairs everywhere for meals or for just relaxing. We traveled as two families and there was more than enough room for all of us. We felt right at home right away. Highly recommend this paradise!

Match: Swimming pool

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Price per night from

$824

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. 1 hour 27 minutes

Match: Swimming pool

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Price per night from

$276

Key Colony Beach Home

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$265

Southard Square Hideaway

Key West condo

1 bedroom / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$90

100 Palo De Oro Drive

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$430

Family Retreat-Ocean front home with private pool

Cudjoe Key house

6 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 3 hours 14 minutes

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Price per night from

$688

Bay Harbour D-114

Long Key house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$328

Spacious Top Floor Condo w/ Water View!!

Marathon apartment

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$373

ROCK HARBOR CLUB P-8

Key Largo house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$103

Welcome Aboard! Relax, unwind, enjoy the water! in key west

Key West yacht

4 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$323

Escape to Paradise --2 bedroom oceanfront condo on Coco Plum

Marathon apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Great condo with beautiful ocean views!!!!” We couldn't have picked a better condo and location!! Many great restaurants and bars only a few miles away. The pool was really nice overlooking the beach. The condo was nicely decorated and plenty of room for just the two us. Enjoyed sitting out on the screened in lanai having our morning coffee or in the evening having a cold drink listening to the waves and enjoying the light of the full moon reflect off the ocean. The Keys are truly a paradise and we will definitely be back and would highly recommend this condo and area to stay!!!

Responds fast! avg. 3 hours 28 minutes

Match: Swimming pool

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Price per night from

$246

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 problems. I would highly recommend this rental

Responds fast! avg. 2 hours 48 minutes

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Price per night from

$656

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

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 31 minutes

Match: Swimming pool

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Price per night from

$205

Canal-Side Home w/ Large Private Dock, Covered Patio & Waterfront Pool

Key Colony Beach house

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$330

Ocean View Penthouse

Tavernier condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 8 minutes

Travelers’ Choice award

Match: Swimming pool

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Price per night from

$252

Best Kept Secret,Port Largo Villas In Key Largo,FL

Key Largo villa

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$224

PALMS 309

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$86

Breathtaking Views on Water !!

Key Largo house

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 1 hour 13 minutes

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Price per night from

$251

TWICE THE CHARM

Key Largo house

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$183

8c, Efficiency located 50 yards from Ocean

Marathon studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 53 minutes

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Price per night from

$189

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$113

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