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Florida Keys Rentals with Pools

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531 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. 3 hours 11 minutes

Match: Swimming pool

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Price per night from

$311

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 14 minutes

Match: Swimming pool

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Price per night from

$344

Match: Swimming pool

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Price per night from

$309

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

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$286

Duck Key 50% off October

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 1 hour 51 minutes

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Price per night from

$339

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 30 minutes

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Price per night from

$1,713

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

Key West townhouse

2 bedrooms / 3 bathrooms / sleeps 6

Match: Swimming pool

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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 23 minutes

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Price per night from

$516

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

$1,228

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

$717

Villa Sombrero, Marathon

Marathon house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 14 minutes

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Price per night from

$655

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 47 minutes

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Price per night from

$458

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

$209

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

Islamorada apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 16 minutes

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Price per night from

$201

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

$143

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. 10 minutes

Match: Swimming pool

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Price per night from

$332

Key Colony Beach Home

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 46 minutes

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Price per night from

$263

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

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

Marathon apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Beautiful location with lots to enjoy!!” This property is exactly as pictured! It was a wonderful vacation with an ideal location.It was right on the ocean so you could watch the sun rise through the screened lanai, along with other various ocean activities.The owners were wonderful to work with and even apologized about parking lot maintenance being completed during our visit, which was no big deal. Please be aware that the property has one of the rare sand beaches in the Keys but seaweed washes up also. Although it can be unsightly, it didn't bother me. The beachcomber does come every few days to clean it up. There was still plenty of sand to the left (North) for me to walk on the beach and search for baby shells. There are so many places to choose for dinners. I recommend Havanna Jack's for oceanfront dining, Florida Keys Steak and Lobster House for lobster, Burdine's for fries and sunset, and Key Colony Inn for early bird special.I truly enjoyed the Dolphin Research Center and also seeing a turtle release from the Turtle Hospital at Sombrero Beach. I enjoyed the heated pool every day because the weather was perfect! If you aren't familiar with the Keys, Marathon is the middle Key. We went to Key West for the day (1 1/2 hr drive) because my friend had never experienced it. The ladies at the Marathon Visitor Center were the best! Great souvenir shop was Marooned in Marathon. You will not believe how many unique gifts they have. I plan to return to this Coco Plum property if/when I am lucky enough to go back to the Keys! I feel we saw alot but there is still so much more to enjoy!

Match: Swimming pool

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Price per night from

$288

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. 3 hours 11 minutes

Match: Swimming pool

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Price per night from

$819

Oceanfront Condo: Ocean Views, Pool, WIFI - Discounted Rate August

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 58 minutes

Match: Swimming pool

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Price per night from

$195

Ocean View Penthouse

Tavernier condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 51 minutes

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Price per night from

$255

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. 21 minutes

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Price per night from

$253

TWICE THE CHARM

Key Largo house

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$250

8c, Efficiency located 50 yards from Ocean

Marathon studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 39 minutes

Match: Swimming pool

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Price per night from

$230

BEACON REEF 310

Islamorada apartment

2 bedrooms / 2 bathrooms / sleeps 4

Match: Swimming pool

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Price per night from

$123

Blue vacation home, water front, boat dock, heated private Pool.

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$555

Waterfront luxury Villa (54) with sunset views and boat slip

Marathon villa

3 bedrooms / 3 bathrooms / sleeps 8

“Beautiful condo in a beautiful setting” Sitting on the front porch watching the sunset was one of the highlights of the trip. And the pool was the best we've ever swam in.

Responds fast! avg. 1 hour 26 minutes

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Price per night from

$1,147

Reef Resort Getaway 205

Marathon studio

Studio / 1 bathroom / sleeps 3

Match: Swimming pool

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Price per night from

$197

LYONS LANDING

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Swimming pool

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Price per night from

$292

Paridise Found

Tavernier house

3 bedrooms / 3 bathrooms / sleeps 13

Match: Swimming pool

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Price per night from

$764

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$344

Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

“Comfortable home for family get-together” Positive experience overall: Our family of six adults had a tropical-feeling destination Christmas here. The house easily accommodated all of us, and we enjoyed the wrap-around porch and pool. We appreciated the commodious kitchen with a two-tier dishwasher and side-by-side refrigerator with ice/water dispenser. Having a washer and dryer on the premises was very helpful, since guests are requested to wash linens and towels before departing. Some drawbacks: the house did not come equipped with adequate staples, such as paper products, laundry detergent, and garbage bags, so be prepared to purchase these. There are no beaches or stores within walking distance. On a couple of nights, noisy neighbors talking on the street woke us up. (In general, though, the area is quiet.)

Responds fast! avg. 15 minutes

Match: Swimming pool

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Price per night from

$670

East Sister Rock Island

Marathon Shores house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$1,713

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