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Key West Vacation Rentals

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

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Air conditioning (25)
Balcony or terrace (35)
DVD player (41)
Dishwasher (64)
Garden (3)
Grill (39)
Heated pool (20)
High Speed Internet (70)
Hot tub/Jacuzzi (8)
Private pool (23)
Sauna (2)
Swimming pool (70)
Washing machine (23)
Wi-Fi available (69)

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Apartment (24)
B&B (1)
Condo (2)
Cottage (4)
House (35)
Studio (1)
Townhouse (2)
Villa (1)

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77 Vacation rentals

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Filters applied: Swimming pool

Distance calculated in a straight line, road distances may differ. Confirm exact location with the property owner/manager.

1 / 25

Sunrise Suite Key West 2 Bed Rooms 2 Full Baths

Key West Condo

2 bedrooms 2
2 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 1 hour 46 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 (83 reviews)

from $240.00 / night

Book

1 / 28

2 bedroom Condo Presented Key West Style

Key West Apartment

2 bedrooms 2
2 bathrooms
sleeps 5 5
min stay varies

Nearest beach 2 mi
Swimming pool
Child friendly

Responds fast! Avg. 55 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 (164 reviews)

from $10.00 / night

Book

1 / 28

6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location

Key West Villa

6 bedrooms 6
7 bathrooms
sleeps 16 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)

from $2,004.00 / night

Book

1 / 22

Harbor Walk Hideaways

Key West B and B

4 bedrooms 4
3 bathrooms
sleeps 8 8
min stay varies

Beach/lakeside relaxation
Nearest beach 0.2 mi
Swimming pool

$901.00

Excellent (21 reviews)

from $901.00 / night

Inquire

1 / 16

Best Old Town Location in Key West. Two blocks from Duval Street.

Key West Townhouse

2 bedrooms 2
3 bathrooms
sleeps 6 6
7 nights min

Nearest beach 1 mi
Swimming pool
Child friendly

“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

$272.00

Excellent (17 reviews)

from $272.00 / night

Inquire

1 / 28

Bahama House - A++ Location with private pool/parking - walk to everything!

Key West House

3 bedrooms 3
4 bathrooms
sleeps 8 8
7 nights min

Swimming pool
Child friendly
Air conditioning

$773.00

from $773.00 / night

Book

1 / 24

Southard Square Hideaway

Key West Condo

1 bedroom 1
1 bathroom
sleeps 4 4
min stay varies

Swimming pool
Child friendly
Air conditioning

$215.00

from $215.00 / night

Inquire

1 / 25

Southard Getaway

Key West Apartment

2 bedrooms 2
1 bathroom
sleeps 5 5
7 nights min

Swimming pool
Child friendly

$195.00

from $195.00 / night

Inquire

1 / 26

Bayview Harbor

Key West Apartment

2 bedrooms 2
1 bathroom
sleeps 5 5
7 nights min

Swimming pool
Child friendly

$160.00

Average (1 reviews)

from $160.00 / night

Inquire

1 / 24

Artist Garden

Key West House

2 bedrooms 2
2 bathrooms
sleeps 6 6
7 nights min

Swimming pool
Child friendly

$285.00

Very Good (27 reviews)

from $285.00 / night

Inquire

1 / 26

President's Walk

Key West House

2 bedrooms 2
1 bathroom
sleeps 4 4
7 nights min

Swimming pool
Child friendly

$195.00

Excellent (1 reviews)

from $195.00 / night

Inquire

1 / 23

William's Loft

Key West Cottage

2 bedrooms 2
1 bathroom
sleeps 3 3
min stay varies

Swimming pool
Child friendly
Pet friendly

$193.00

from $193.00 / night

Inquire

1 / 23

Sunshine Key West

Key West House

2 bedrooms 2
3 bathrooms
sleeps 5 5
min stay varies

Swimming pool
Child friendly

$297.00

Excellent (1 reviews)

from $297.00 / night

Inquire

1 / 27

Lighthouse Villa

Key West House

3 bedrooms 3
4 bathrooms
sleeps 8 8
min stay varies

Swimming pool
Child friendly
Air conditioning

$445.00

from $445.00 / night

Inquire

1 / 24

Key West Found

Key West House

2 bedrooms 2
2 bathrooms
sleeps 6 6
7 nights min

Swimming pool
Child friendly

$250.00

Very Good (32 reviews)

from $250.00 / night

Inquire

1 / 25

Big house

Key West House

5 bedrooms 5
5 bathrooms
sleeps 10 10
min stay varies

Swimming pool
Child friendly
Air conditioning

$700.00

Excellent (5 reviews)

from $700.00 / night

Inquire

1 / 25

Newton's Nest

Key West Apartment

1 bedroom 1
1 bathroom
sleeps 2 2
min stay varies

Swimming pool
Ask about children
Ask about pets

$167.00

from $167.00 / night

Inquire

1 / 24

First Breath

Key West House

3 bedrooms 3
2 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Child friendly
Pet friendly

$289.00

from $289.00 / night

Inquire

1 / 23

Emma's Escape

Key West Apartment

2 bedrooms 2
1 bathroom
sleeps 4 4
min stay varies

Swimming pool
Child friendly

$185.00

Excellent (4 reviews)

from $185.00 / night

Inquire

1 / 24

Finn Key

Key West Apartment

2 bedrooms 2
1 bathroom
sleeps 4 4
7 nights min

Swimming pool
Child friendly

$180.00

Very Good (33 reviews)

from $180.00 / night

Inquire

1 / 24

Crowner's Jewel

Key West House

2 bedrooms 2
2 bathrooms
sleeps 6 6
7 nights min

Swimming pool
Child friendly

$205.00

Very Good (35 reviews)

from $205.00 / night

Inquire

1 / 24

Duval Breeze

Key West House

2 bedrooms 2
2 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Child friendly
Air conditioning

$240.00

Very Good (57 reviews)

from $240.00 / night

Inquire

1 / 27

A Barefoot Retreat

Key West Apartment

2 bedrooms 2
1 bathroom
sleeps 4 4
7 nights min

Swimming pool
Child friendly

$180.00

Very Good (1 reviews)

from $180.00 / night

Inquire

1 / 16

Boat House

Key West House

1 bedroom 1
2 bathrooms
sleeps 2 2
min stay varies

Swimming pool
Child friendly
Air conditioning

$215.00

from $215.00 / night

Inquire

1 / 24

A Place In Paradise

Key West House

2 bedrooms 2
2 bathrooms
sleeps 6 6
7 nights min

Swimming pool
Child friendly

$235.00

Very Good (23 reviews)

from $235.00 / night

Inquire

1 / 27

Linger Longer

Key West House

2 bedrooms 2
1 bathroom
sleeps 5 5
7 nights min

Swimming pool
Child friendly

$185.00

Very Good (22 reviews)

from $185.00 / night

Inquire

1 / 22

Conch Republic Retreat

Key West Cottage

2 bedrooms 2
2 bathrooms
sleeps 4 4
min stay varies

Swimming pool
Child friendly
Air conditioning

$238.00

from $238.00 / night

Inquire

1 / 24

City Cay

Key West Apartment

1 bedroom 1
1 bathroom
sleeps 2 2
7 nights min

Swimming pool
Child friendly
Air conditioning

$152.00

Very Good (4 reviews)

from $152.00 / night

Inquire

1 / 24

Verandah

Key West House

2 bedrooms 2
2 bathrooms
sleeps 4 4
min stay varies

Swimming pool
Child friendly

$278.00

Very Good (11 reviews)

from $278.00 / night

Inquire

1 / 24

Tranquility

Key West Cottage

1 bedroom 1
1 bathroom
sleeps 4 4
min stay varies

Swimming pool
Child friendly
Air conditioning

$180.00

Very Good (31 reviews)

from $180.00 / night

Inquire

1 / 24

Ibis

Key West House

1 bedroom 1
1 bathroom
sleeps 2 2
min stay varies

Swimming pool
Child friendly
Pet friendly

$167.00

Very Good (2 reviews)

from $167.00 / night

Inquire

1 / 23

Sundown Refuge

Key West Apartment

2 bedrooms 2
2 bathrooms
sleeps 5 5
7 nights min

Swimming pool
Child friendly

$264.00

Excellent (10 reviews)

from $264.00 / night

Inquire

1 / 25

Flagler Station

Key West House

3 bedrooms 3
2 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Child friendly

$278.00

Excellent (1 reviews)

from $278.00 / night

Inquire

1 / 24

Amelia Home

Key West House

2 bedrooms 2
2 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Child friendly
Air conditioning

$315.00

Very Good (57 reviews)

from $315.00 / night

Inquire

1 / 27

tropical Casita

Key West House

1 bedroom 1
2 bathrooms
sleeps 2 2
min stay varies

Swimming pool
Child friendly
Pet friendly

$242.00

from $242.00 / night

Inquire

1 / 24

Shrimp Party

Key West Townhouse

2 bedrooms 2
2 bathrooms
sleeps 4 4
min stay varies

Swimming pool
Child friendly

$247.00

from $247.00 / night

Inquire

1 / 22

Key Lime Pie

Key West House

2 bedrooms 2
2 bathrooms
sleeps 4 4
min stay varies

Swimming pool
Child friendly
Pet friendly

$219.00

Average (7 reviews)

from $219.00 / night

Inquire

1 / 18

Perfect Pineapple

Key West House

2 bedrooms 2
1 bathroom
sleeps 4 4
min stay varies

Swimming pool
Child friendly
Pet friendly

$242.00

Very Good (9 reviews)

from $242.00 / night

Inquire

1 / 24

Rosalie's House

Key West House

3 bedrooms 3
2 bathrooms
sleeps 8 8
min stay varies

Swimming pool
Child friendly
Pet friendly

$297.00

from $297.00 / night

Inquire

1 / 24

Emma's Secret

Key West Apartment

2 bedrooms 2
1 bathroom
sleeps 4 4
min stay varies

Swimming pool
Child friendly

$186.00

Excellent (1 reviews)

from $186.00 / night

Inquire

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This is the estimated nightly price based on a weekly stay. Contact the advertiser to confirm the price - it varies depending on when you stay and how long for.

This is the estimated nightly price based on a weekly stay.

Estimated price per night based on a weekly stay. Owner fees of {FEE} per stay may apply.

This is the total cost of the stay for the dates and number of guests that you entered.

This price is an estimate based on the latest rate information available to us. Contact the advertiser to ask for the exact price, including any additional fees.

Rates for this rental are unknown, please contact the homeowner to confirm the rate.

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