- Owners / Managers
- Travelers
- List your property
- Travelers
Help
Deals
Discover
Manage your booking
$ USD

Travelers

Sign in
Join
Manage your booking
$ USD
Help
Deals

Owners

Owner login
List your property
Help

Search 105,200+ Vacation Rentals

Where do you want to go? ✕

Check in

Check out

Sleeps Sleeps

Adults

Children

Search

All Vacation Rentals

Key West Vacation Rentals

Key West Vacation Rentals & House Rentals with Swimming Pool - 66 Rentals Available.

Min price

Max price

Bedrooms

Adults

Children

More Filters Fewer Filters

Air conditioning (66)
Balcony or terrace (41)
DVD player (41)
Dishwasher (9)
Garden (12)
Grill (30)
Heated pool (58)
High Speed Internet (66)
Hot tub/Jacuzzi (8)
Private pool (48)
Swimming pool (66)
Washing machine (8)
Wi-Fi available (64)

More

Less

Apartment (22)
B&B (1)
Condo (3)
Cottage (1)
Guest house (1)
House (35)
Studio (1)
Townhouse (1)
Yacht (1)

More

Less

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

66 Vacation rentals

Sort by:

Filters applied: Swimming pool

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

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

“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

$216.00

Excellent (139 reviews)

from $216.00 / night

Book

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 / 19

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

$225.00

from $225.00 / night

Book

1 / 15

Beautiful Large 2BR KINGs (or twins) condo,deck and patio, Truman Anx, Pool

Key West Condo

2 bedrooms 2
1 bathroom
Sleeps 4 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

$325.00

Excellent (5 reviews)

from $325.00 / night

Book

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

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 (62 reviews)

from $209.00 / night

Book

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

$393.00

Excellent (4 reviews)

from $393.00 / night

Inquire

1 / 14

Beautiful, End-Unit 2BR King/twins, Private with Lg deck. Truman Annx. Pool

Key West Condo

2 bedrooms 2
1 bathroom
Sleeps 4 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

$207.00

Very Good (5 reviews)

from $207.00 / night

Book

1 / 22

Harbor Walk Hideaways

Key West B and B

4 bedrooms 4
3 bathrooms
Sleeps 8 8
3 nights min

Beach/lakeside relaxation
Nearest beach 0.2 mi
Swimming pool

$801.00

Excellent (20 reviews)

from $801.00 / night

Inquire

1 / 17

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 / 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 / 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 / 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 / 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

$744.00

from $744.00 / 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 / 24

Lavender Jungle

Key West Apartment

2 bedrooms 2
1 bathroom
Sleeps 4 4
Min stay varies

Swimming pool
Child friendly
Air conditioning

$160.00

Very Good (25 reviews)

from $160.00 / 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

$175.00

Very Good (29 reviews)

from $175.00 / night

Inquire

1 / 24

Here Tomorrow

Key West House

3 bedrooms 3
2 bathrooms
Sleeps 6 6
Min stay varies

Swimming pool
Child friendly
Air conditioning

$256.00

Excellent (1 reviews)

from $256.00 / night

Inquire

1 / 24

Conch Adventure

Key West Apartment

2 bedrooms 2
1 bathroom
Sleeps 4 4
Min stay varies

Swimming pool
Child friendly
Air conditioning

$160.00

from $160.00 / night

Inquire

1 / 24

A Place In Paradise

Key West House

2 bedrooms 2
2 bathrooms
Sleeps 6 6
Min stay varies

Swimming pool
Child friendly
Air conditioning

$225.00

Very Good (23 reviews)

from $225.00 / night

Inquire

1 / 24

Breezy Bungalow

Key West House

2 bedrooms 2
2 bathrooms
Sleeps 4 4
Min stay varies

Swimming pool
Child friendly
Air conditioning

$225.00

Excellent (1 reviews)

from $225.00 / night

Inquire

1 / 24

City Cay

Key West Apartment

1 bedroom 1
1 bathroom
Sleeps 2 2
Min stay varies

Swimming pool
Child friendly
Air conditioning

$160.00

Excellent (3 reviews)

from $160.00 / night

Inquire

1 / 23

Sundown Refuge

Key West Apartment

2 bedrooms 2
2 bathrooms
Sleeps 5 5
Min stay varies

Swimming pool
Child friendly
Air conditioning

$300.00

Excellent (9 reviews)

from $300.00 / night

Inquire

1 / 24

Linger Longer

Key West House

2 bedrooms 2
1 bathroom
Sleeps 5 5
Min stay varies

Swimming pool
Child friendly
Air conditioning

$195.00

Very Good (22 reviews)

from $195.00 / night

Inquire

1 / 24

President's Walk

Key West House

2 bedrooms 2
1 bathroom
Sleeps 4 4
Min stay varies

Swimming pool
Child friendly
Air conditioning

$180.00

Excellent (1 reviews)

from $180.00 / night

Inquire

1 / 25

Easy Livin'

Key West House

3 bedrooms 3
4 bathrooms
Sleeps 8 8
Min stay varies

Swimming pool
Child friendly
Air conditioning

$500.00

Excellent (1 reviews)

from $500.00 / night

Inquire

1 / 24

Key West Found

Key West House

2 bedrooms 2
2 bathrooms
Sleeps 6 6
Min stay varies

Swimming pool
Child friendly
Air conditioning

$250.00

Very Good (31 reviews)

from $250.00 / night

Inquire

1 / 28

Shipyard Treasure

Key West Apartment

2 bedrooms 2
1 bathroom
Sleeps 4 4
Min stay varies

Swimming pool
Child friendly
Air conditioning

$210.00

Excellent (52 reviews)

from $210.00 / night

Inquire

1 / 24

Atlantic Paradise

Key West Apartment

2 bedrooms 2
2 bathrooms
Sleeps 6 6
Min stay varies

Swimming pool
Child friendly
Air conditioning

$201.00

from $201.00 / night

Inquire

1 / 23

Island Wind

Key West House

2 bedrooms 2
2 bathrooms
Sleeps 4 4
Min stay varies

Swimming pool
Child friendly
Air conditioning

$225.00

Excellent (10 reviews)

from $225.00 / night

Inquire

1 / 24

Coral Casita

Key West House

3 bedrooms 3
3 bathrooms
Sleeps 8 8
Min stay varies

Swimming pool
Child friendly
Air conditioning

$210.00

Excellent (4 reviews)

from $210.00 / night

Inquire

1 / 24

A Barefoot Retreat

Key West Apartment

2 bedrooms 2
1 bathroom
Sleeps 4 4
Min stay varies

Swimming pool
Child friendly
Air conditioning

$170.00

Very Good (1 reviews)

from $170.00 / night

Inquire

1 / 24

Alluring Porches

Key West House

3 bedrooms 3
3 bathrooms
Sleeps 6 6
Min stay varies

Swimming pool
Child friendly
Air conditioning

$275.00

Very Good (16 reviews)

from $275.00 / night

Inquire

1 / 24

Captains Wheel

Key West House

2 bedrooms 2
2 bathrooms
Sleeps 6 6
Min stay varies

Swimming pool
Child friendly
Air conditioning

$210.00

from $210.00 / night

Inquire

1 / 24

Southard Getaway

Key West Apartment

2 bedrooms 2
1 bathroom
Sleeps 5 5
Min stay varies

Swimming pool
Child friendly
Air conditioning

$195.00

from $195.00 / night

Inquire

1 / 24

Key West Casa

Key West House

3 bedrooms 3
2 bathrooms
Sleeps 6 6
Min stay varies

Swimming pool
Child friendly
Air conditioning

$300.00

Very Good (26 reviews)

from $300.00 / 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

$300.00

Very Good (54 reviews)

from $300.00 / night

Inquire

1 / 24

Artist Garden

Key West House

2 bedrooms 2
2 bathrooms
Sleeps 4 4
Min stay varies

Swimming pool
Child friendly
Air conditioning

$275.00

Very Good (27 reviews)

from $275.00 / night

Inquire

1 / 24

Finn Key

Key West Apartment

2 bedrooms 2
1 bathroom
Sleeps 4 4
Min stay varies

Swimming pool
Child friendly
Air conditioning

$180.00

Very Good (33 reviews)

from $180.00 / night

Inquire

1 / 24

Truman's Hideaway

Key West Apartment

2 bedrooms 2
2 bathrooms
Sleeps 5 5
Min stay varies

Swimming pool
Child friendly
Air conditioning

$275.00

Very Good (11 reviews)

from $275.00 / night

Inquire

1 / 24

Bayview Harbor

Key West Apartment

2 bedrooms 2
1 bathroom
Sleeps 5 5
Min stay varies

Swimming pool
Child friendly
Air conditioning

$180.00

from $180.00 / night

Inquire

Page 1 of 2

1 2 Next Last

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.

Discover

Rental type
Property type
- Key West Apartment rentals
Worldwide destinations
- Florida
- Fort Myers
- Ocean City
- Destin
- Panama City Beach
- Orlando
- Myrtle Beach
- Cape Cod
- Virginia Beach
- Galveston
Other suggestions

Find a Rental
About Us
Terms

Copyright© 2018 Vacation Home Rentals. All rights reserved

See the details for this home, contact the owner, pay for your trip and more!

Go to manage your vacation booking

1

Need to think it over?

Send yourself an email so you can come back to book this property.

Enter your email address

The Enter your email address field is required. The "Enter your email address" field must contain a valid email address.

To get help making a booking, call our dedicated Reservations team at:

+1-857-504-6968

+1-857-504-6968

24 hours, 7 days a week