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Florida Keys Vacation Rentals & House Rentals with Swimming Pool - 71 Rentals Available.

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71 Vacation rentals

Filters applied: Swimming pool

1 / 23

Marathon Townhouse

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$245

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from $245 / night

(4)

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 (4 reviews)

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from $233 / 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

$134

Excellent (3 reviews)

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from $134 / 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

(125)

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

$210

Excellent (125 reviews)

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from $210 / 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

1 / 24

Duck Key Villa

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

from $340 / night

(48)

1 / 34

Cudjoe Key House

  • 6
  • 14
  • Min stay varies
  • Nearest beach 10 mi
  • Swimming pool
  • Child friendly

$457

Very Good (48 reviews)

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from $457 / night

(7)

1 / 9

Islamorada House

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
“We had four couples on our summer fishing vacation that we do every year in Islamorada.Couldnt have been better,we had couple days at first to go feed tarpon at Robbies and relax till seas calmed down and we got out in flat waters to fish,we caught...”
- Review left on 05/29/2015

$429

Excellent (7 reviews)

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from $429 / 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

(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

(53)

1 / 36

Key West Condo

  • 2
  • 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • 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 (53 reviews)

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from $209 / night

1 / 24

Key Largo Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool

$155

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from $155 / night

(1)

1 / 23

Marathon Shores House

  • 4
  • 10
  • Min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly

$358

Excellent (1 reviews)

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from $358 / 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

(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

1 / 25

Marathon House

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

from $350 / night

(2)

1 / 23

Cudjoe Key House

  • 2
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 30 mi
  • Swimming pool
“The view was outstanding, the property had great amenities, and the home had all items as advertised. We were happy campers...”
- Review left on 03/13/2017

$173

Very Good (2 reviews)

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from $173 / night

(9)

1 / 14

Islamorada House

  • 3
  • 8
  • Min stay varies
  • 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

$420

Excellent (9 reviews)

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from $420 / 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

(15)

1 / 16

Islamorada Condo

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“The house was so nice, everything you could possible need. The view from the lanai is superb, Bobbie was a great owner, would answer your call for anything. The complex is quiet, and the people are friendly. What an amazing vacation...”
- Review left on 11/11/2016

$200

Excellent (15 reviews)

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from $200 / 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

(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

(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 / 24

Duck Key Villa

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

from $535 / night

(20)

1 / 22

Key West B and B

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

$730

Excellent (20 reviews)

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from $730 / night

(2)

1 / 18

Key West Condo

  • 3
  • 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$209

Excellent (2 reviews)

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from $209 / 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

(27)

1 / 16

Key Largo Villa

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“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 (27 reviews)

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from $300 / 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

(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

(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

(18)

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 (18 reviews)

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from $100 / night

(2)

1 / 17

Key Largo Townhouse

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Norm was thorough in the walk through of the property we stayed. Townhouse condo was clean and well stocked. Next to salt water lagoon and pool. All the water toys were made available like snorkels, fins, fishing rods, kayaks and paddleboards. Golf...”
- Review left on 03/25/2017

$250

Excellent (2 reviews)

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from $250 / 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 / 16

Marathon Shores Townhouse

  • 4
  • 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$450

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from $450 / night

1 / 5

Marathon Shores Townhouse

  • 3
  • 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$285

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from $285 / night

(29)

1 / 17

Marathon Villa

  • 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

$358

Excellent (29 reviews)

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from $358 / 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

(2)

1 / 31

Marathon House

  • 12
  • 30
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool

$798

Excellent (2 reviews)

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from $798 / night