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Florida Keys Vacation Rentals & House Rentals with Swimming Pool - 74 Rentals Available.

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74 Vacation rentals

Filters applied: Swimming pool

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

(121)

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 (121 reviews)

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from $200 / night

(7)

1 / 12

Key West Condo

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$250

Very Good (7 reviews)

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from $250 / night

(5)

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 (5 reviews)

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from $228 / night

(1)

1 / 23

Marathon Shores House

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

$358

Excellent (1 reviews)

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from $358 / 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

(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

$187

Very Good (5 reviews)

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from $187 / night

1 / 24

Duck Key Villa

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

from $340 / 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

1 / 25

Marathon House

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

from $320 / night

(20)

1 / 22

Key West B and B

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

$731

Excellent (20 reviews)

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from $731 / night

(10)

1 / 17

Marathon House

  • 3
  • 8
  • Min stay varies
  • 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

(9)

1 / 14

Islamorada House

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

$450

Excellent (9 reviews)

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from $450 / 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)

1 / 15

Key Largo Condo

  • 2
  • 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We really enjoyed our stay at your beautiful property. The condo had everything we needed, from comfortable beds to a well-equipped kitchen. We especially enjoyed the view, fishing off the dock, barbequing and being able to walk to many great...”
- Review left on 12/11/2016

$145

Excellent (1 reviews)

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from $145 / night

(2)

1 / 16

Tavernier Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“My family and I had a fabulous time. Enjoyed all the perks available. Close to a local shopping center which has everything you may need. We will be back...”
- Review left on 12/02/2016

$175

Excellent (2 reviews)

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from $175 / 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

(3)

1 / 55

Key West Villa

  • 5
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“I rented this house for my sister-in-law's bachelorette weekend. The house was spacious, clean, and overall one of the best houses we've stayed in...”
- Review left on 09/27/2016

$829

Excellent (3 reviews)

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from $829 / night

(3)

1 / 37

Key West House

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“This home was more than expected. It was close enough to all the night life of Duval Street, yet are enough to enjoy peace and quiet when needed. I would recommend this home to anyone looking for a great vacation getaway...”
- Review left on 05/20/2015

$355

Very Good (3 reviews)

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from $355 / night

(13)

1 / 15

Tavernier House

  • 4
  • 12
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Comfortable home in a super-quiet neighborhood. Easily accommodated 8 adults. Plenty of room at the dining table for dining, cards, and games. Generous kitchen allowed milling about and food prep participation. Good beds and pillows; good bathrooms....”
- Review left on 02/07/2017

$300

Excellent (13 reviews)

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from $300 / 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

(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

$500

Excellent (8 reviews)

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from $500 / 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

$104

Excellent (1 reviews)

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from $104 / night

1 / 24

Duck Key Villa

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

from $535 / night

(51)

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 (51 reviews)

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from $209 / 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

(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

$714

Very Good (12 reviews)

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from $714 / 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

(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

$167

Excellent (3 reviews)

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from $167 / 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

$1071

Excellent (2 reviews)

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from $1071 / night

(15)

1 / 19

Marathon House

  • 3
  • 8
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Close to everything! We did it all from this beach house...Not to mention it was clean and very well stocked. Lucy was amazing from beginning the process all the way to the last day...”
- Review left on 07/30/2015

$250

Very Good (15 reviews)

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from $250 / night

(15)

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 (15 reviews)

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from $286 / night

(13)

1 / 17

Marathon House

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Peninsular House ? Marathon, Florida We had a great time celebrating our 25th Wedding Anniversary at the Peninsular House ? gives you the feel of what ?old Florida? would be like - away from everyone, but actually just a hop, skip and jump from...”
- Review left on 05/25/2017

$315

Very Good (13 reviews)

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from $315 / night

(1)

1 / 34

Key Largo House

  • 4
  • 14
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Thank you for letting us use your home for our family vacation. We enjoyed every part of it. Used the kayaks several times, used the pool 24/7 and really enjoyed the out doors. We brought our boat and we managed to get in and out of the narrow canal...”
- Review left on 07/20/2015

$200

Excellent (1 reviews)

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from $200 / night

(17)

1 / 17

Key West Townhouse

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Car not necessary
“This unit was great! The location is fantastic! The condo is spacious, clean and everything we were hoping for. I like that the bedrooms are upstairs which offers more privacy...”
- Review left on 01/12/2017

$200

Excellent (17 reviews)

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from $200 / 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

(26)

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 (26 reviews)

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from $300 / night

1 / 17

Key Largo Condo

  • 2
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

from $94 / 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

(1)

1 / 27

Key Largo House

  • 3
  • 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$160

Excellent (1 reviews)

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from $160 / night