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Key West Vacation Rentals & House Rentals with Swimming Pool - 77 Rentals Available.

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77 Vacation rentals

Filters applied: Swimming pool

(83)

Certificate of Excellence

1 / 25

Key West Condo

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

Responds fast! Avg. 2 hours 4 minutes

Travelers’ Choice award

“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 (83 reviews)

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from $240.00 / night

(165)

1 / 28

Key West Apartment

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

Responds fast! Avg. 40 minutes

“Accommodations are perfect- easy to access, not too far from the sites and beaches! Building is very quiet even with a rather large pool area...”
- Review left on 02/20/2019

$10.00

Excellent (165 reviews)

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from $10.00 / night

(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

$2,004.00

Excellent (3 reviews)

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from $2,004.00 / night

(21)

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 (21 reviews)

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from $900.00 / night

1 / 28

Key West House

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

$773.00

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from $773.00 / night

1 / 24

Key West Condo

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

$215.00

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from $215.00 / night

1 / 25

Key West Apartment

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

$195.00

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from $195.00 / night

(1)

1 / 26

Key West Apartment

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

$160.00

Average (1 reviews)

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from $160.00 / night

(27)

1 / 25

Key West House

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

$285.00

Very Good (27 reviews)

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from $285.00 / night

(1)

1 / 26

Key West House

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

$195.00

Excellent (1 reviews)

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from $195.00 / night

1 / 23

Key West Cottage

  • 2
  • 3
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$194.00

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from $194.00 / night

1 / 27

Key West House

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

$445.00

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from $445.00 / night

(32)

1 / 24

Key West House

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

$250.00

Very Good (32 reviews)

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from $250.00 / night

(5)

1 / 25

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

1 / 25

Key West Apartment

  • 1
  • 2
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$167.00

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from $167.00 / night

1 / 24

Key West House

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$289.00

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from $289.00 / night

(4)

1 / 23

Key West Apartment

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

$185.00

Excellent (4 reviews)

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from $185.00 / night

(33)

1 / 24

Key West Apartment

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

$180.00

Very Good (33 reviews)

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from $180.00 / night

(35)

1 / 24

Key West House

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

$200.00

Very Good (35 reviews)

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from $200.00 / night

1 / 24

Key West House

  • 1
  • 2
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$208.00

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from $208.00 / night

(57)

1 / 24

Key West House

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

$241.00

Very Good (57 reviews)

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from $241.00 / night

(1)

1 / 27

Key West Apartment

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

$180.00

Very Good (1 reviews)

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from $180.00 / night

1 / 16

Key West House

  • 1
  • 2
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$215.00

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from $215.00 / night

(23)

1 / 24

Key West House

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

$225.00

Very Good (23 reviews)

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from $225.00 / night

(22)

1 / 27

Key West House

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

$180.00

Very Good (22 reviews)

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from $180.00 / night

1 / 22

Key West Cottage

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

$238.00

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from $238.00 / night

(4)

1 / 24

Key West Apartment

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

$152.00

Very Good (4 reviews)

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from $152.00 / night

(11)

1 / 24

Key West House

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

$278.00

Very Good (11 reviews)

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from $278.00 / night

(31)

1 / 24

Key West Cottage

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

$175.00

Very Good (31 reviews)

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from $175.00 / night

(2)

1 / 24

Key West House

  • 1
  • 2
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$167.00

Very Good (2 reviews)

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from $167.00 / night

(10)

1 / 23

Key West Apartment

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

$264.00

Excellent (10 reviews)

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from $264.00 / night

(1)

1 / 25

Key West House

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$278.00

Excellent (1 reviews)

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from $278.00 / night

(57)

1 / 24

Key West House

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

$325.00

Very Good (57 reviews)

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from $325.00 / night

1 / 27

Key West House

  • 1
  • 2
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$241.00

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from $241.00 / night

1 / 24

Key West Townhouse

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

$247.00

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from $247.00 / night

(7)

1 / 22

Key West House

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

$219.00

Average (7 reviews)

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from $219.00 / night

(9)

1 / 18

Key West House

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

$241.00

Very Good (9 reviews)

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from $241.00 / night

1 / 24

Key West House

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

$297.00

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from $297.00 / night

(1)

1 / 24

Key West Apartment

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

$186.00

Excellent (1 reviews)

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from $186.00 / night

(26)

1 / 24

Key West Apartment

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

$150.00

Very Good (26 reviews)

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from $150.00 / night