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Florida Keys Vacation Rentals & House Rentals with Swimming Pool - 95 Rentals Available.

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95 Vacation rentals

Filters applied: Swimming pool

(7)

1 / 12

Key West Condo

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$295

Very Good (7 reviews)

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from $295 / night

1 / 23

Marathon Townhouse

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$245

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from $245 / night

1 / 9

Long Key House

  • 5
  • 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $357 / night

(17)

1 / 42

Key Largo Cottage

  • 1
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool
“Our family of 4 stayed here over Thanksgiving week and had the best time. Penny is very organized and everything was perfect, love the ambiance. We love the old Florida feel and the tiki hut is the best. Our teenage boys had a fantastic time swimming...”
- Review left on 04/14/2016

$100

Excellent (17 reviews)

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from $100 / night

1 / 20

Matecumbe Key Townhouse

  • 2
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $100 / night

(1)

1 / 23

Marathon Shores House

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$425

Excellent (1 reviews)

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from $425 / night

(4)

1 / 15

Key West Condo

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly
“We stayed for a week and had a wonderful holiday. The booking and communication with the owner was good and the accommodation is exactly as described. It is a lovely clean well equipped apartment in a central location. Easy walk to all of the...”
- Review left on 07/13/2016

$228

Excellent (4 reviews)

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from $228 / night

(11)

1 / 16

Marathon House

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“The house and lush landscaping are beautiful! We enjoyed the pool so much. The private dock is a great touch even though we don't have a boat. We would recommend this property highly! Quaint restaurants in Marathon have some great food, too! We...”
- Review left on 11/03/2014

$393

Excellent (11 reviews)

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from $393 / night

(9)

1 / 14

Islamorada House

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Had a great time. Beautiful house. Very convenient to everything. We highly recommend this property...”
- Review left on 08/05/2016

$395

Excellent (9 reviews)

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from $395 / night

(3)

1 / 33

Islamorada House

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We enjoy coming back, weather just great. Just so relaxing. Chiki bar, pool, private dock all a plus. Est place to vacation...”
- Review left on 10/17/2016

$457

Excellent (3 reviews)

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from $457 / night

(119)

1 / 28

Key West Apartment

  • 2
  • 6
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
“we can"t say enough about the condo or Pam. She takes good care of her rental. Always clean and comfortable.The balcony overlooks the pool area which is well maintained. Pam is always available to answer any questions you might have. We stay the...”
- Review left on 12/03/2016

$200

Excellent (119 reviews)

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from $200 / night

1 / 25

Marathon House

  • 4
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $300 / night

(2)

1 / 18

Key Largo House

  • 3
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“The owners were wonderful to work with; their house was spacious, comfortable, and well-appointed and updated; and the location was a great spot from which to take excursions. Highly recommend...”
- Review left on 01/03/2017

$142

Excellent (2 reviews)

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from $142 / night

(1)

1 / 20

Key Colony Beach Condo

  • 2
  • 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Great location on the water. Pleasant heated large pool. Small number of units and lots of room on the grounds. Pier and beach. Clean, quiet, and well kept inside and out by owners there. Got an invite to meet for a birthday party and got to...”
- Review left on 02/06/2016

$103

Excellent (1 reviews)

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from $103 / night

(48)

1 / 34

Cudjoe Key House

  • 6
  • 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$415

Very Good (48 reviews)

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from $415 / night

(3)

1 / 15

Tavernier House

  • 5
  • 10
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We have just returned from a month long celebration of retirement in the Keys. The lovely home we stayed in was perfectly located smack dab in the middle of everything there is to do in the Keys! The owner of this property was quick to respond to...”
- Review left on 02/05/2016

$168

Excellent (3 reviews)

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from $168 / night

(50)

1 / 36

Key West Condo

  • 2
  • 6
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We enjoyed our stay at the Sunrise Suite. The place was bright with sunshine. It was clean, comfortable, nice sitting balcony and close to Duval Street. It had everything you would need for your stay. You could walk thru the complex and cross the...”
- Review left on 03/06/2017

$209

Excellent (50 reviews)

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from $209 / night

(12)

1 / 24

Islamorada House

  • 5
  • 15
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This is the second time we've rented this house and it was better than the first time. Beautiful views and easy access to the bay was exactly what we were looking for. The new ice maker and huge refrigerator were perfect for our large group. Amazing...”
- Review left on 07/11/2016

$643

Very Good (12 reviews)

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from $643 / night

(3)

1 / 6

Key West Apartment

  • 2
  • 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$295

Very Good (3 reviews)

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from $295 / night

(12)

1 / 14

Key Largo House

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“My wife,daughters and me , stay in these place for a week ,, and really ,, its not enough . Quiet,reserved,peaceful and a lot restaurant for the best breakfast and dinner in the keys .If you enjoy and like scuba diving or snorkeling ..... perfect ....”
- Review left on 07/17/2016

$130

Very Good (12 reviews)

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from $130 / night

(10)

1 / 28

Marathon House

  • 5
  • 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“# families, 8 kids ranging from 2-14yrs stayed here for a week. Absolutely could not be happier! Pool was fantastic and warm, hot tub was well maintained, and clean. Grounds were breathtakingly beautiful. Kyaks were readily available, and easy to get...”
- Review left on 01/19/2017

$415

Very Good (10 reviews)

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from $415 / night

(5)

1 / 14

Key West Condo

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly
“We (2 retired couples) enjoyed our stay at Rooster Retreat. What you see in the pictures is true to what you get, but I will add that the "twins to king conversion" is probably the best I have ever experienced. It just did not "feel" like twins --...”
- Review left on 03/12/2017

$186

Very Good (5 reviews)

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from $186 / night

(7)

1 / 8

Key Colony Beach Condo

  • 2
  • 4
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We truly enjoyed every minute of this beautiful condo in Key Colony Beach for the month of March, 2015. From the decor to the amazing views from the balcony, we were so happy with all the amenities. The kitchen was well equipped with everything we...”
- Review left on 04/05/2015

$160

Excellent (7 reviews)

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from $160 / night

(14)

1 / 18

Marathon Villa

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This was our second time staying here. It's a great location, very comfortable and well-equipped house and so peaceful. The owner is great to work with. Can't wait to stay here again...”
- Review left on 01/09/2017

$286

Excellent (14 reviews)

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from $286 / night

(2)

1 / 73

Marathon House

  • 5
  • 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“They went the extra mile with this home. Everything was great, everything you need is there for cooking. Caught fish from the dock during high tide . Top notch will stay again...”
- Review left on 11/11/2016

$929

Excellent (2 reviews)

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from $929 / night

(11)

1 / 60

Key Largo Condo

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We loved your place. It is so nicely decorated, furnished with everything we could have needed and so very clean! I loved being able to walk to the water and fish from the pier. It was hard to decide whether to go in the pool, ocean or ping pong...”
- Review left on 02/08/2017

$128

Excellent (11 reviews)

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from $128 / night

1 / 24

Duck Key Villa

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $340 / night

(8)

1 / 10

Islamorada House

  • 3
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“What a lovely place. Immaculately clean and beautifully appointed. Everything as advertised and the pool and hot tub are beautiful. Nicely situated in Lower Metacumbe. The private beach was a gorgeous addition. We had a wonderful time and Capt....”
- Review left on 03/24/2016

$400

Excellent (8 reviews)

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from $400 / night

(16)

1 / 15

Key Largo House

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Great place for family who like boating, fishing, diving, snorkeling and have fun in the beautiful reef at John Penny Camp State under water park. I recommended to everyone I know. This place is awesome!! I am a HAPPY Camper...”
- Review left on 08/23/2016

$350

Very Good (16 reviews)

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from $350 / night

(10)

1 / 17

Marathon House

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Following our wedding in the Caribbean we booked this house as part of our honeymoon sharing the house with our teenage sons and another couple. The house and location was perfect for us, our only regret that we didn't have longer. The house itself...”
- Review left on 08/01/2016

$314

Very Good (10 reviews)

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from $314 / night

1 / 16

Marathon House

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$1000

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from $1000 / night

(18)

1 / 26

Marathon House

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool

$372

Excellent (18 reviews)

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from $372 / night

(2)

1 / 34

Key Colony Beach House

  • 7
  • 16
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Wonderful house and plenty of space for our party of 14. Pool was wonderful and everyone was very comfortable...”
- Review left on 07/26/2016

$629

Very Good (2 reviews)

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from $629 / night

(3)

1 / 31

Marathon House

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Stayed with my family of 5. Plenty of room, great spot. Would recommend. Check pics, they are true to the rental...”
- Review left on 03/18/2017

$427

Very Good (3 reviews)

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from $427 / night

(3)

1 / 20

Summerland Key House

  • 4
  • 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This house was great. Had everything you could ask for. The owner even called to make sure we made it ok and if we needed anything. Best view, plenty of space absolutely gorgeous couldn't of asked for better...”
- Review left on 08/19/2014

$233

Excellent (3 reviews)

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from $233 / night

(8)

1 / 8

Marathon House

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“It could not have been better. The owners were excellent, and the home had everything imaginable. We will be back...”
- Review left on 12/25/2016

$243

Excellent (8 reviews)

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from $243 / night

1 / 8

Sugarloaf Key House

  • 5
  • 10
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $500 / night

(1)

1 / 43

Marathon House

  • 4
  • 10
  • 7 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Ask about children
“This place is absolutely AMAZING! We stayed here with 3 families and we had plenty of room. Everything from the beautifully maintained grounds to the spacious house made this stay amazing! The views of the sunsets from the balcony were outstanding....”
- Review left on 10/01/2016

$300

Excellent (1 reviews)

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from $300 / night

(1)

1 / 24

Marathon House

  • 4
  • 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$257

Excellent (1 reviews)

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from $257 / night

(25)

1 / 16

Key Largo Villa

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This place was awesome-everything included we had paddle boards, Kayaks, golf cart and bicycles. The host Norman couldn't have been more friendly and helpful. I recommend this getaway to anyone and it is pet friendly...”
- Review left on 01/19/2017

$300

Very Good (25 reviews)

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from $300 / night