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Key West Vacation Rentals & House Rentals with Swimming Pool - 15 Rentals Available.

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15 Vacation rentals

Filters applied: Swimming pool

(7)

1 / 12

Key West Condo

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

$296

Very Good (7 reviews)

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from $296 / night

(118)

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 (118 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

(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

$1196

Excellent (3 reviews)

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from $1196 / 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 / 15

Key West House

  • 3
  • 6
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“I have stayed at the Brass Palm Villa several times and I would never stay anywhere else on the island. It is decorated beautifully and exceptionally well maintained. There are many places to relax inside and outside the home. I especially enjoy the...”
- Review left on 10/10/2010

$200

Excellent (3 reviews)

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from $200 / night

(9)

1 / 4

Key West Townhouse

  • 2
  • 4
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Traveling Buddies (3) rented this beautiful, recently renovated single-family townhouse in February, 2012 for two weeks. The house is so perfect in everyway-fully equipped...close to Duval St yet behind the gate and setback from busy Truman, its...”
- Review left on 03/27/2012

$100

Excellent (9 reviews)

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from $100 / night

(3)

1 / 6

Key West Apartment

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

$296

Very Good (3 reviews)

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from $296 / 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

(2)

1 / 18

Key West Condo

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

$284

Excellent (2 reviews)

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from $284 / 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

(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

(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

(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

(1)

1 / 21

Key West House

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Howard was great to work with. The house was very nicely furnished. The pool area is small but this is key west. The location was great. Overall very good experience...”
- Review left on 02/09/2016

$583

Very Good (1 reviews)

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from $583 / night

Your search has been expanded 40.7 miles to include more rentals

1 / 8

Sugarloaf Key House - 26 miles away

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

from $500 / night

(48)

1 / 34

Cudjoe Key House - 31.9 miles away

  • 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 / 20

Summerland Key House - 40.7 miles away

  • 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