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Key West Vacation Rentals & House Rentals with Swimming Pool - 96 Rentals Available.

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96 Vacation rentals

Filters applied: Swimming pool

(70)

Certificate of Excellence

1 / 25

Key West Condo

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

Responds fast! Avg. 3 hours 16 minutes

Certificate of Excellence

“The Condo had such a beachy feel you knew you were on vacation. It was so clean and had anything you needed. Very nice pool also. The location was great only a 10-minute drive to any main attraction. Would highly recommend this unit as we will...”
- Review left on 12/10/2018

$240.00

Excellent (70 reviews)

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from $240.00 / night

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(148)

1 / 28

Key West Apartment

  • 2
  • 5
  • min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 11 minutes

“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

$211.00

Excellent (148 reviews)

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from $211.00 / night

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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

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(3)

1 / 28

Key West Villa

  • 6
  • 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • 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

$1,432.00

Excellent (3 reviews)

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from $1,432.00 / night

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1 / 12

Key West House

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

$466.00

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from $466.00 / night

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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

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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

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(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

$394.00

Excellent (4 reviews)

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from $394.00 / night

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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

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(20)

1 / 22

Key West B and B

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

$900.00

Excellent (20 reviews)

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from $900.00 / night

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1 / 28

Key West House

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$682.00

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from $682.00 / night

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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

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(17)

1 / 10

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

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1 / 24

Key West Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$169.00

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from $169.00 / night

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1 / 24

Key West Apartment

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Child friendly

$195.00

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from $195.00 / night

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(1)

1 / 24

Key West House

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

$195.00

Excellent (1 reviews)

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from $195.00 / night

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1 / 23

Key West Apartment

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Child friendly

$180.00

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from $180.00 / night

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(27)

1 / 24

Key West House

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

$285.00

Very Good (27 reviews)

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from $285.00 / night

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(5)

1 / 24

Key West House

  • 5
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$700.00

Excellent (5 reviews)

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from $700.00 / night

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(32)

1 / 24

Key West House

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

$250.00

Very Good (32 reviews)

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from $250.00 / night

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(1)

1 / 23

Key West House

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly

$276.00

Excellent (1 reviews)

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from $276.00 / night

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1 / 24

Key West Apartment

  • 1
  • 2
  • min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$148.00

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from $148.00 / night

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1 / 24

Key West House

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$270.00

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from $270.00 / night

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1 / 24

Key West House

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$157.00

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from $157.00 / night

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(56)

1 / 24

Key West House

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

$240.00

Very Good (56 reviews)

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from $240.00 / night

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(28)

1 / 23

Key West House

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly

$156.00

Very Good (28 reviews)

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from $156.00 / night

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(35)

1 / 24

Key West House

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

$200.00

Very Good (35 reviews)

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from $200.00 / night

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(2)

1 / 24

Key West House

  • 1
  • 2
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$154.00

Very Good (2 reviews)

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from $154.00 / night

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1 / 24

Key West House

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

$157.00

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from $157.00 / night

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1 / 24

Key West House

  • 1
  • 2
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$207.00

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from $207.00 / night

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(4)

1 / 23

Key West Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly

$156.00

Excellent (4 reviews)

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from $156.00 / night

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(4)

1 / 21

Key West House

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

$235.00

Very Good (4 reviews)

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from $235.00 / night

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(6)

1 / 24

Key West House

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

$210.00

Excellent (6 reviews)

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from $210.00 / night

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(33)

1 / 24

Key West Apartment

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

$180.00

Very Good (33 reviews)

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from $180.00 / night

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(11)

1 / 23

Key West House

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

$225.00

Excellent (11 reviews)

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from $225.00 / night

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(30)

1 / 24

Key West Cottage

  • 1
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$175.00

Very Good (30 reviews)

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from $175.00 / night

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(22)

1 / 24

Key West House

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Child friendly

$195.00

Very Good (22 reviews)

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from $195.00 / night

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(3)

1 / 24

Key West Apartment

  • 1
  • 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$152.00

Excellent (3 reviews)

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from $152.00 / night

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1 / 24

Key West House

  • 1
  • 2
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$193.00

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from $193.00 / night

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(1)

1 / 24

Key West Apartment

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

$180.00

Very Good (1 reviews)

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from $180.00 / night

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