Search 105,200+ Vacation Rentals
✕

Key West Vacation Rentals & House Rentals with Swimming Pool - 61 Rentals Available.

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

61 Vacation rentals

Filters applied: Swimming pool

(121)

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 (121 reviews)

Book

from $200 / night

Book

(3)

1 / 6

Key West Apartment

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

$295

Very Good (3 reviews)

Book

from $295 / night

Book

(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)

Inquire

from $228 / night

Inquire

(7)

1 / 12

Key West Condo

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

$250

Very Good (7 reviews)

Book

from $250 / night

Book

(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)

Inquire

from $187 / night

Inquire

(20)

1 / 22

Key West B and B

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

$731

Excellent (20 reviews)

Book

from $731 / night

Book
1 / 18

Key West Condo

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

$209

Book

from $209 / night

Book

(51)

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 (51 reviews)

Inquire

from $209 / night

Inquire

(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)

Inquire

from $200 / night

Inquire

(1)

1 / 25

Key West House

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$583

Excellent (1 reviews)

Inquire

from $583 / night

Inquire

(6)

1 / 24

Key West Apartment

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

$375

Very Good (6 reviews)

Inquire

from $375 / night

Inquire

(52)

1 / 28

Key West Apartment

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

$215

Excellent (52 reviews)

Inquire

from $215 / night

Inquire

(29)

1 / 24

Key West Cottage

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$215

Very Good (29 reviews)

Inquire

from $215 / night

Inquire

(1)

1 / 24

Key West House

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

$245

Average (1 reviews)

Inquire

from $245 / night

Inquire

(11)

1 / 24

Key West Apartment

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

$315

Very Good (11 reviews)

Inquire

from $315 / night

Inquire

(1)

1 / 24

Key West House

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

$275

Excellent (1 reviews)

Inquire

from $275 / night

Inquire

(10)

1 / 23

Key West House

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

$275

Excellent (10 reviews)

Inquire

from $275 / night

Inquire

(56)

1 / 24

Key West House

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

$346

Very Good (56 reviews)

Inquire

from $346 / night

Inquire

(54)

1 / 24

Key West House

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

$346

Very Good (54 reviews)

Inquire

from $346 / night

Inquire

(3)

1 / 26

Key West House

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

$929

Excellent (3 reviews)

Inquire

from $929 / night

Inquire
1 / 24

Key West Apartment

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

$230

Inquire

from $230 / night

Inquire

(35)

1 / 24

Key West House

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$275

Very Good (35 reviews)

Inquire

from $275 / night

Inquire

(32)

1 / 24

Key West Apartment

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

$205

Very Good (32 reviews)

Inquire

from $205 / night

Inquire

(4)

1 / 24

Key West House

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

$245

Excellent (4 reviews)

Inquire

from $245 / night

Inquire

(30)

1 / 24

Key West Apartment

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

$230

Very Good (30 reviews)

Inquire

from $230 / night

Inquire

(28)

1 / 24

Key West Apartment

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

$165

Very Good (28 reviews)

Inquire

from $165 / night

Inquire

(25)

1 / 24

Key West House

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

$325

Very Good (25 reviews)

Inquire

from $325 / night

Inquire

(36)

1 / 23

Key West House

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

$275

Very Good (36 reviews)

Inquire

from $275 / night

Inquire
1 / 24

Key West Apartment

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

$215

Inquire

from $215 / night

Inquire

(3)

1 / 25

Key West Apartment

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

$205

Very Good (3 reviews)

Inquire

from $205 / night

Inquire

(11)

1 / 24

Key West Apartment

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

$235

Very Good (11 reviews)

Inquire

from $235 / night

Inquire

(27)

1 / 23

Key West House

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

$195

Very Good (27 reviews)

Inquire

from $195 / night

Inquire

(28)

1 / 23

Key West Apartment

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

$250

Very Good (28 reviews)

Inquire

from $250 / night

Inquire

(9)

1 / 23

Key West Apartment

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

$330

Excellent (9 reviews)

Inquire

from $330 / night

Inquire

(23)

1 / 24

Key West House

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$275

Very Good (23 reviews)

Inquire

from $275 / night

Inquire

(2)

1 / 24

Key West Apartment

  • 1
  • 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$190

Excellent (2 reviews)

Inquire

from $190 / night

Inquire

(4)

1 / 24

Key West House

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

$805

Excellent (4 reviews)

Inquire

from $805 / night

Inquire

(16)

1 / 24

Key West House

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

$290

Very Good (16 reviews)

Inquire

from $290 / night

Inquire

(26)

1 / 24

Key West House

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

$595

Very Good (26 reviews)

Inquire

from $595 / night

Inquire

(49)

1 / 24

Key West House

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

$240

Very Good (49 reviews)

Inquire

from $240 / night

Inquire