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Key West Vacation Rentals

Key West Vacation Rentals & House Rentals with Swimming Pool - 97 Rentals Available.

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Air conditioning (13)
Balcony or terrace (49)
DVD player (44)
Dishwasher (8)
Garden (10)
Grill (45)
Heated pool (72)
High Speed Internet (84)
Hot tub/Jacuzzi (9)
Private pool (66)
Swimming pool (84)
Washing machine (7)
Wi-Fi available (82)

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Apartment (26)
B&B (1)
Condo (1)
Cottage (1)
Guest house (1)
House (50)
Studio (1)
Townhouse (1)
Villa (1)
Yacht (1)

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97 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. 3 hours 20 minutes

Certificate of Excellence

“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

$209.00

Excellent (69 reviews)

from $209.00 / 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. 1 hour 26 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

$215.00

Excellent (145 reviews)

from $215.00 / night

Book

1 / 8

Key's only real beach home.Gated, private, dock,pool

Key West House

3 bedrooms 3
2 bathrooms
sleeps 6 6
7 nights min

Swimming pool
Child friendly
Air conditioning

$536.00

from $536.00 / night

Inquire

1 / 9

Key's only real beach home. Dock and pool.

Key West House

2 bedrooms 2
1 bathroom
sleeps 4 4
min stay varies

Nearest beach 0 mi
Swimming pool
Child friendly

$343.00

from $343.00 / night

Inquire

1 / 11

The Key's only real beach house Dock and pool

Key West House

2 bedrooms 2
2 bathrooms
sleeps 4 4
7 nights min

Swimming pool
Child friendly
Air conditioning

$394.00

from $394.00 / night

Inquire

1 / 28

Key West Vacation Rental - The Duval Street Compound

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

$1,250.00

Excellent (3 reviews)

from $1,250.00 / night

Book

1 / 17

SPECIAL DISCOUNT! 45' Sailboat & Other Yachts

Key West Yacht

2 bedrooms 2
2 bathrooms
sleeps 6 6
min stay varies

Beach/lakeside relaxation
Swimming pool
Ask about children

Responds fast! Avg. 3 hours 31 minutes

$199.00

from $199.00 / night

Book

1 / 10

Best Old Town Location in Key West

Key West Townhouse

2 bedrooms 2
3 bathrooms
sleeps 6 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)

from $258.00 / night

Inquire

1 / 11

Key West's only Real Beach House

Key West Guest house

2 bedrooms 2
2 bathrooms
sleeps 4 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)

from $394.00 / night

Inquire

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

$900.00

Excellent (20 reviews)

from $900.00 / night

Inquire

1 / 12

Private beach estate. Gated, tropical peace and quiet. Dock.

Key West House

2 bedrooms 2
1 bathroom
sleeps 4 4
min stay varies

Nearest beach 0 mi
Swimming pool
Child friendly

$465.00

from $465.00 / night

Inquire

1 / 26

Private beach estate,gated,dock,and pool.

Key West House

5 bedrooms 5
3 bathrooms
sleeps 10 10
28 nights min

Nearest beach 0 mi
Swimming pool
Child friendly

$743.00

from $743.00 / night

Inquire

1 / 16

Private beach estate.Dock and pool.

Key West House

3 bedrooms 3
2 bathrooms
sleeps 6 6
30 nights min

Nearest beach 0 mi
Swimming pool
Child friendly

$284.00

from $284.00 / night

Inquire

1 / 24

Coral Casita

Key West House

3 bedrooms 3
3 bathrooms
sleeps 8 8
min stay varies

Swimming pool
Child friendly
Pet friendly

$225.00

Excellent (5 reviews)

from $225.00 / night

Inquire

1 / 24

Wind Swept

Key West House

2 bedrooms 2
1 bathroom
sleeps 6 6
min stay varies

Swimming pool
Child friendly

$157.00

Average (2 reviews)

from $157.00 / 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

$225.00

Very Good (23 reviews)

from $225.00 / night

Inquire

1 / 23

Sunshine Key West

Key West House

2 bedrooms 2
3 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Child friendly

$286.00

Excellent (1 reviews)

from $286.00 / night

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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 (9 reviews)

from $264.00 / night

Inquire

1 / 23

Island Wind

Key West House

2 bedrooms 2
2 bathrooms
sleeps 4 4
7 nights min

Swimming pool
Child friendly

$230.00

Excellent (11 reviews)

from $230.00 / night

Inquire

1 / 24

Key West Casa

Key West House

3 bedrooms 3
2 bathrooms
sleeps 6 6
7 nights min

Swimming pool
Child friendly

$325.00

Very Good (26 reviews)

from $325.00 / night

Inquire

1 / 24

Bahama House

Key West House

3 bedrooms 3
3 bathrooms
sleeps 7 7
7 nights min

Swimming pool
Child friendly

$495.00

Very Good (27 reviews)

from $495.00 / night

Inquire

1 / 24

The Dolphin House

Key West House

4 bedrooms 4
3 bathrooms
sleeps 8 8
7 nights min

Swimming pool
Child friendly

$600.00

Very Good (3 reviews)

from $600.00 / 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 / 24

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 / 24

Tropical Dreaming

Key West House

2 bedrooms 2
2 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Child friendly
Pet friendly

$325.00

Very Good (59 reviews)

from $325.00 / 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

$166.00

Excellent (4 reviews)

from $166.00 / 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

$155.00

from $155.00 / night

Inquire

1 / 24

Conch Condo

Key West Apartment

2 bedrooms 2
2 bathrooms
sleeps 4 4
7 nights min

Swimming pool
Child friendly

$191.00

Very Good (11 reviews)

from $191.00 / 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 / 24

Duval Sea Turtle

Key West House

2 bedrooms 2
2 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Child friendly

$210.00

Very Good (49 reviews)

from $210.00 / night

Inquire

1 / 24

Big house

Key West House

5 bedrooms 5
5 bathrooms
sleeps 12 12
min stay varies

Swimming pool
Child friendly

$700.00

Excellent (5 reviews)

from $700.00 / 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

$200.00

Very Good (35 reviews)

from $200.00 / night

Inquire

1 / 24

A Little Slice Of Paradise

Key West House

2 bedrooms 2
1 bathroom
sleeps 6 6
min stay varies

Swimming pool
Child friendly
Pet friendly

$157.00

from $157.00 / night

Inquire

1 / 21

Duval On The Square

Key West House

2 bedrooms 2
2 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Child friendly
Pet friendly

$234.00

Very Good (4 reviews)

from $234.00 / 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

$166.00

Excellent (1 reviews)

from $166.00 / night

Inquire

1 / 24

Bahamian Reed

Key West House

2 bedrooms 2
1 bathroom
sleeps 5 5
7 nights min

Swimming pool
Child friendly

$180.00

Average (1 reviews)

from $180.00 / night

Inquire

1 / 22

Parrot Perch

Key West Apartment

2 bedrooms 2
2 bathrooms
sleeps 5 5
7 nights min

Swimming pool
Child friendly

$200.00

Very Good (23 reviews)

from $200.00 / night

Inquire

1 / 24

Truman's Hideaway

Key West Apartment

2 bedrooms 2
2 bathrooms
sleeps 5 5
7 nights min

Swimming pool
Child friendly

$225.00

Very Good (11 reviews)

from $225.00 / night

Inquire

1 / 25

The Hemingway

Key West House

2 bedrooms 2
2 bathrooms
sleeps 4 4
7 nights min

Swimming pool
Child friendly

$210.00

Average (27 reviews)

from $210.00 / night

Inquire

1 / 24

Key West Charming

Key West Apartment

2 bedrooms 2
1 bathroom
sleeps 4 4
7 nights min

Swimming pool
Child friendly

$140.00

Very Good (26 reviews)

from $140.00 / 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.

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.

What is Certificate of Excellence?

TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travelers.

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