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Key West Vacation Rentals & House Rentals with Swimming Pool - 65 Rentals Available.

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65 Vacation rentals

Filters applied: Swimming pool

(7)

1 / 12

Key West Condo

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

$275

Very Good (7 reviews)

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from $275 / 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

(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

(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

(3)

1 / 28

Key West Villa

  • 6
  • 16
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“This house is great for large groups. We had such a fun time having a reunion here. Close to everything, and staff was attentive and friendly...”
- Review left on 09/08/2016

$1195

Excellent (3 reviews)

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from $1195 / 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

(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

(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

(1)

1 / 23

Key West House

  • 3
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This house is immaculately kept and one of the few houses on a canal in KW. Beautiful interior and plenty of room in the bedrooms. The pool overlooks the canal and has an absolutely beautiful view! If you want a house that makes you feel like you're...”
- Review left on 03/10/2015

$133

Excellent (1 reviews)

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from $133 / 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

$356

Very Good (3 reviews)

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from $356 / 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

(16)

1 / 21

Key West House

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We rented Casa Rosa with three other couples for a week in February, 2017. Location was terrific! We could walk to many restaurants,bars, beaches and one grocery store (Fausto's). Suitable size for 8 people. Liked that each couple had their own...”
- Review left on 03/05/2017

$541

Very Good (16 reviews)

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from $541 / night

(2)

1 / 18

Key West Condo

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

$195

Excellent (2 reviews)

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from $195 / night

(28)

1 / 24

Key West Apartment

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$250

Very Good (28 reviews)

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from $250 / night

(25)

1 / 24

Key West House

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$325

Very Good (25 reviews)

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from $325 / night

(9)

1 / 23

Key West Apartment

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$330

Excellent (9 reviews)

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from $330 / night

(4)

1 / 24

Key West House

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$245

Excellent (4 reviews)

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from $245 / night

(36)

1 / 23

Key West House

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$275

Very Good (36 reviews)

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from $275 / night

(30)

1 / 24

Key West Apartment

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$230

Very Good (30 reviews)

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from $230 / night

(26)

1 / 24

Key West House

  • 3
  • 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$595

Very Good (26 reviews)

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from $595 / night

(52)

1 / 28

Key West Apartment

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$215

Excellent (52 reviews)

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from $215 / night

(56)

1 / 24

Key West House

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$240

Very Good (56 reviews)

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from $240 / night

(22)

1 / 24

Key West House

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$230

Very Good (22 reviews)

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from $230 / night

(6)

1 / 24

Key West Apartment

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$375

Very Good (6 reviews)

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from $375 / night

1 / 24

Key West House

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from $275 / night

(49)

1 / 22

Key West House

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$240

Very Good (49 reviews)

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from $240 / night

(25)

1 / 24

Key West Apartment

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$205

Very Good (25 reviews)

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from $205 / night

(27)

1 / 23

Key West House

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$195

Very Good (27 reviews)

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from $195 / night

(11)

1 / 24

Key West Apartment

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$315

Very Good (11 reviews)

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from $315 / night

(24)

1 / 24

Key West House

  • 3
  • 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$595

Very Good (24 reviews)

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from $595 / night

(56)

1 / 23

Key West House

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$345

Very Good (56 reviews)

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from $345 / night

(32)

1 / 24

Key West Apartment

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$205

Very Good (32 reviews)

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from $205 / night

(16)

1 / 24

Key West House

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$290

Very Good (16 reviews)

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from $290 / night

(3)

1 / 26

Key West House

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$929

Excellent (3 reviews)

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from $929 / night

(54)

1 / 24

Key West House

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$345

Very Good (54 reviews)

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from $345 / night

(28)

1 / 24

Key West Apartment

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$165

Very Good (28 reviews)

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from $165 / night

(11)

1 / 24

Key West House

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$245

Very Good (11 reviews)

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from $245 / night

(4)

1 / 24

Key West House

  • 5
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$805

Excellent (4 reviews)

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from $805 / night

(27)

1 / 24

Key West House

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$315

Very Good (27 reviews)

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from $315 / night

(3)

1 / 24

Key West House

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$665

Very Good (3 reviews)

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from $665 / night