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Florida Keys Vacation Rentals & House Rentals with Swimming Pool - 127 Rentals Available.

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127 Vacation rentals

Filters applied: Swimming pool

(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

$325.00

Excellent (5 reviews)

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from $325.00 / night

(2)

1 / 17

Tavernier Condo

  • 2
  • 6
  • 1 night min
  • 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

$235.00

Excellent (2 reviews)

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from $235.00 / night

(7)

1 / 22

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

$322.00

Excellent (7 reviews)

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from $322.00 / night

1 / 19

Key West Yacht

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$200.00

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from $200.00 / night

1 / 19

Marathon Shores Townhouse

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

$325.00

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from $325.00 / night

(2)

1 / 29

Cudjoe Key House

  • 2
  • 6
  • Min stay varies
  • 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

$175.00

Very Good (2 reviews)

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from $175.00 / night

(12)

1 / 17

Marathon House

  • 3
  • 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“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

$436.00

Excellent (12 reviews)

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from $436.00 / night

(1)

1 / 43

Marathon House

  • 4
  • 10
  • 7 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
“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

$300.00

Excellent (1 reviews)

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from $300.00 / night

1 / 12

Key West House

  • 2
  • 4
  • Min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$465.00

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from $465.00 / night

1 / 25

Marathon House

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

$350.00

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from $350.00 / night

(139)

1 / 28

Key West Apartment

  • 2
  • 5
  • 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

$215.00

Excellent (139 reviews)

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from $215.00 / night

1 / 20

Marathon Shores Townhouse

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

$476.00

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from $476.00 / night

(62)

Certificate of Excellence

1 / 25

Key West Condo

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Certificate of Excellence

“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

$210.00

Excellent (62 reviews)

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from $210.00 / night

(9)

1 / 14

Islamorada House

  • 3
  • 8
  • 7 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

$450.00

Excellent (9 reviews)

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from $450.00 / night

1 / 17

Summerland Key House

  • 3
  • 6
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$142.00

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from $142.00 / night

1 / 23

Marathon Townhouse

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

$245.00

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from $245.00 / 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

$207.00

Very Good (5 reviews)

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from $207.00 / night

(18)

1 / 39

Key Largo Cottage

  • 1
  • 5
  • 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

$140.00

Excellent (18 reviews)

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from $140.00 / night

1 / 24

Duck Key Villa

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

$400.00

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from $400.00 / night

(20)

1 / 22

Key West B and B

  • 4
  • 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

$800.00

Excellent (20 reviews)

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from $800.00 / night

(19)

1 / 27

Islamorada House

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“This house is the best!!!!! We had two familys staying and was perfect. The separate living quarters made our trip very enjoyable and very roomy. The house upstairs is remarkable and very up to date as well as downstairs. The back yard is your own...”
- Review left on 08/09/2016

$458.00

Excellent (19 reviews)

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from $458.00 / night

(1)

1 / 16

Marathon House

  • 4
  • 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“My family and I went and stayed at this house for a week and had the most amazing time. The house was buitiful and very clean. The place had everything for the kids as well and for me to. I can't thank them enough for letting us stay in their...”
- Review left on 10/02/2016

$429.00

Excellent (1 reviews)

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from $429.00 / night

(1)

1 / 27

Key Largo House

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

$160.00

Excellent (1 reviews)

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from $160.00 / night

(17)

1 / 17

Key West Townhouse

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • 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

$258.00

Excellent (17 reviews)

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from $258.00 / 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

$400.00

Very Good (27 reviews)

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from $400.00 / night

(1)

1 / 11

Marathon Shores House

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

$400.00

Excellent (1 reviews)

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from $400.00 / night

(36)

1 / 19

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

$358.00

Very Good (36 reviews)

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from $358.00 / night

(4)

1 / 11

Key West Guest house

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We rented the Conch House for our honeymoon and it was perfect! We loved the secluded feeling and the private beach. Carol was wonderful to work with and had fresh eggs and champagne waiting for us in our fridge. She picked fresh veggies for us to...”
- Review left on 04/20/2016

$393.00

Excellent (4 reviews)

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from $393.00 / night

1 / 8

Key Largo House

  • 1
  • 2
  • 2 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

$125.00

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from $125.00 / night

(16)

1 / 15

Key Largo House

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

$250.00

Very Good (16 reviews)

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from $250.00 / night

1 / 8

Key West House

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$536.00

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from $536.00 / night

(2)

1 / 17

Key Largo Townhouse

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

$250.00

Excellent (2 reviews)

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from $250.00 / 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

$286.00

Excellent (8 reviews)

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from $286.00 / night

1 / 16

Key West House

  • 3
  • 6
  • 30 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$284.00

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from $284.00 / night

1 / 26

Key West House

  • 5
  • 10
  • 28 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$743.00

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from $743.00 / night

1 / 14

Key Largo House

  • 4
  • 8
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$200.00

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from $200.00 / night

1 / 9

Key West House

  • 2
  • 4
  • Min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$343.00

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from $343.00 / night

1 / 11

Key West House

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$394.00

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from $394.00 / night

1 / 25

Tavernier House

  • 2
  • 6
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

$199.00

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from $199.00 / night

(25)

1 / 24

Key West Apartment

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$160.00

Very Good (25 reviews)

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from $160.00 / night