Holiday Homes in Key West

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Find holiday rentals that suit your style

Houseboat image
Houseboats
Houseboats
apart-hotel image
Aparthotels
Aparthotels

Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Key West holiday homes

A building with a red door, a covered porch, and a bamboo plant in the foreground.

1. Road's End | Prime Old Town Location! Updated Home w/ Pool

Road's End | Prime Old Town Location! Updated Home w/ Pool
Old Town Key West
9.6 out of 10, Exceptional, (28 reviews)
"Charming, clean accommodations in a conveniently located area of Key West for walking to sites and renting bicycles"
United States
BARBARA Y.
The price is €377
includes taxes & fees
15 Nov - 16 Nov
Road's End | Prime Old Town Location! Updated Home w/ Pool
A patio area with a fountain, seating, and umbrellas.

2. Andros Suite | Perfect Location with Pool!

Andros Suite | Perfect Location with Pool!
Old Town Key West
10.0 out of 10, Exceptional, (5 reviews)
"Great little place 1 block off Duval. A nice quiet oasis from everything a street away. Moon Dog restaurant is around the block and was great for breakfast and dinner. Great kitchen! The mattress upstairs could use a firmer replacement IMHO…overall very good spot!"
United States
Robert J.
The price is €393
includes taxes & fees
30 Nov - 1 Dec
Andros Suite | Perfect Location with Pool!
A porch with wooden chairs and a table, a wooden door with green shutters, and a white railing.

3. Shared Pool & Near Duval - Curry House Room 9

Shared Pool & Near Duval - Curry House Room 9
Old Town Key West
7.4 out of 10, Good, (20 reviews)
"Nice and clean.Quiet and convenient to Duval.We will be back!"
United States
Deborah L.
The price is €283
includes taxes & fees
18 Nov - 19 Nov
Shared Pool & Near Duval - Curry House Room 9
A wooden deck with a large tree, outdoor seating, and a marina in the background.

4. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Wonderful stay. Thank you."
United States
shannon b.
The price is €271
includes taxes & fees
29 Nov - 30 Nov
Poolside Cottage #412
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

5. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (72 reviews)
"I loved having the pool right outside the door! It was extremely clean and perfectly located for our needs. I really enjoyed sitting outside in the evenings. I would absolutely stay here again and recommend it to others!"
United States
Cristy D.
The price is €280
includes taxes & fees
1 Dec - 2 Dec
Poolside Cottage #411
A covered porch with a table and chairs, a view of the street, and a building with a balcony.

6. Casa Havana | Old Town Condo w/ Pool & Balcony

Casa Havana | Old Town Condo w/ Pool & Balcony
Old Town Key West
9.2 out of 10, Wonderful, (12 reviews)
"Wonderful location, clean, quiet. All around it was a great experience staying here!"
United States
Kim T.
The price is €656
includes taxes & fees
16 Nov - 17 Nov
Casa Havana | Old Town Condo w/ Pool & Balcony
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with bar stools.

7. Sea Esta Suite | Located On Iconic Duval w/ Pool

Sea Esta Suite | Located On Iconic Duval w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (58 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
United States
Rick H.
The price is €644
includes taxes & fees
10 Nov - 11 Nov
Sea Esta Suite | Located On Iconic Duval w/ Pool
A covered porch with white railings and multiple Adirondack chairs.

8. Luxury two floor apartment in prime location of famous Duval Street

Luxury two floor apartment in prime location of famous Duval Street
Old Town Key West
9.6 out of 10, Exceptional, (104 reviews)
"Great stay at a great location. Apartment was very clean. Enjoyed the balcony overlooking Duval St. "
United States
Gregory L.
The price is €659
includes taxes & fees
16 Nov - 17 Nov
Luxury two floor apartment in prime location of famous Duval Street
A clear swimming pool with lounge chairs and palm trees.

9. Slice of Paradise

Slice of Paradise
Stock Island
10.0 out of 10, Exceptional, (5 reviews)
"House was clean, what we expected, host responded promptly and accurately, pool was great."
United States
Cathy S.
The price is €489
includes taxes & fees
17 Nov - 18 Nov
Slice of Paradise
A patio area with wicker furniture and a grill.

10. Southernmost Retreat | On Duval! With Hot Tub, Patio

Southernmost Retreat | On Duval! With Hot Tub, Patio
Old Town Key West
9.6 out of 10, Exceptional, (35 reviews)
"Awesome place great location communication with host was great would stay here again next time I’m in key west."
United States
Drew L.
The price is €825
includes taxes & fees
16 Nov - 17 Nov
Southernmost Retreat | On Duval! With Hot Tub, Patio
A swimming pool with a curved edge, surrounded by palm trees and lounge chairs.

11. Poolside Paradise

Poolside Paradise
Stock Island
The price is €515
includes taxes & fees
9 Nov - 10 Nov
Poolside Paradise
A covered outdoor seating area with a sofa, chairs, and a coffee table.

12. Coconut Palm - Steps from Duval with Private Pool

Coconut Palm - Steps from Duval with Private Pool
Old Town Key West
9.0 out of 10, Wonderful, (39 reviews)
"Great Property Excellent location "
United States
Jim B.
The price is €835
includes taxes & fees
17 Nov - 18 Nov
Coconut Palm - Steps from Duval with Private Pool
A covered outdoor patio with a pool, seating area, and lush greenery.

13. Coconut Palm by Brightwild Island Home w Pool

Coconut Palm by Brightwild Island Home w Pool
2.0 star property
Old Town Key West
The price is €922
includes taxes & fees
17 Nov - 18 Nov
Coconut Palm by Brightwild Island Home w Pool
A two-story house with a porch, a blue door, and a brick pathway leading to the entrance.

14. Keys Breeze - Walk to Duval, Private Pool

Keys Breeze - Walk to Duval, Private Pool
Old Town Key West
9.8 out of 10, Exceptional, (41 reviews)
"Great place, location, clean and climate controlled. Pool was great and the host was excellent!"
United States
Lisa S.
The price is €1,003
includes taxes & fees
16 Nov - 17 Nov
Keys Breeze - Walk to Duval, Private Pool
A backyard with a swimming pool, wooden deck, and a covered patio area.

15. Conch Cove | Private Oasis with Heated Pool!

Conch Cove | Private Oasis with Heated Pool!
Old Town Key West
9.8 out of 10, Exceptional, (44 reviews)
"Wonderful spot and outstanding property management company. "
United States
Jessica B.
The price is €1,070
includes taxes & fees
16 Nov - 17 Nov
Conch Cove | Private Oasis with Heated Pool!
An outdoor patio with a table and chairs, a ceiling fan, and a decorative fence.

16. Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St

Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
Old Town Key West
9.4 out of 10, Exceptional, (58 reviews)
"Great location and we would stay here again. "
United States
Brandon A.
The price is €830
includes taxes & fees
8 Nov - 9 Nov
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
A wooden deck with two lounge chairs and a gazebo surrounded by lush greenery.

17. Atlantis House Suites

Atlantis House Suites
Midtown
10.0 out of 10, Exceptional, (3 reviews)
"Awesome place to stay ! Located just close enough and just far away enough . Highly recommended "
United States
Aaron J.
The price is €724
includes taxes & fees
9 Nov - 10 Nov
Atlantis House Suites
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

18. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
Stock Island
9.6 out of 10, Exceptional, (139 reviews)
"We had an awesome stay! We enjoyed being able to use the bikes and have covered parking, too. We would definitely stay here again!"
United States
Melanie K.
The price is €567
includes taxes & fees
9 Nov - 10 Nov
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A pool area with a hot tub, outdoor seating, and a wooden fence with pool rules posted.

19. Private Parking, Heated Pool - Sweet Caroline

Private Parking, Heated Pool - Sweet Caroline
Key West Historic District
9.0 out of 10, Wonderful, (33 reviews)
"Amazing home and location! So close to Duval and all the fun places. I highly recommend staying here. Very comfy, clean and convenient."
United States
Susana C.
The price is €713
includes taxes & fees
29 Nov - 30 Nov
Private Parking, Heated Pool - Sweet Caroline
A clear swimming pool surrounded by palm trees and lounge chairs, with a building in the background.

20. Spacious 3-bedroom townhome on Stock Island with resort style pool.

Spacious 3-bedroom townhome on Stock Island with resort style pool.
Stock Island
10.0 out of 10, Exceptional, (8 reviews)
"Perfect for our family trip to Key West. Great location and we enjoyed the pool and nearby restaurants. Easy check in and check out process and clear, timely communication with the owner. "
United States
Samantha P.
The price is €536
includes taxes & fees
23 Nov - 24 Nov
Spacious 3-bedroom townhome on Stock Island with resort style pool.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Learn more about Key West

Stroll Duval Street's colourful shops and bars before catching the sunset celebration at Mallory Square with local performers. Explore Hemingway's historic home where six-toed cats roam freely, then snorkel the vibrant coral reefs just offshore.

See all hotels in Key West
A sign for the Key West Museum of Art & History at the Custom House.

Explore a world of travel with Expedia