A sunny street lined with historic buildings, a 'ONE WAY' sign, and a flagpole with flags.

Search Vacation 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

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Key West vacation homes

A wooden deck with a large tree, outdoor seating, and a marina in the background.

1. 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 SAR 625
SAR 1,129 total
includes taxes & fees
18 Oct - 19 Oct
Poolside Cottage #412
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with bar stools.

2. 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, (55 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
United States
Rick H.
The price is SAR 694
SAR 2,790 total
includes taxes & fees
29 Oct - 30 Oct
Sea Esta Suite | Located On Iconic Duval w/ Pool
A patio area with a fountain, seating, and umbrellas.

3. 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 SAR 533
SAR 1,689 total
includes taxes & fees
18 Oct - 19 Oct
Andros Suite | Perfect Location with Pool!
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

4. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (70 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 SAR 625
SAR 1,144 total
includes taxes & fees
18 Oct - 19 Oct
Poolside Cottage #411
A covered porch with a table and chairs, a view of the street, and a building with a balcony.

5. 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, (11 reviews)
"Wonderful location, clean, quiet. All around it was a great experience staying here!"
United States
Kim T.
The price is SAR 1,285
SAR 3,136 total
includes taxes & fees
12 Nov - 13 Nov
Casa Havana | Old Town Condo w/ Pool & Balcony
An aerial view of a beach with clear turquoise waters, a sandy shore, and a dense forested area.

6. 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, (103 reviews)
"Great stay at a great location. Apartment was very clean. Enjoyed the balcony overlooking Duval St. "
United States
Gregory L.
The price is SAR 1,108
SAR 2,702 total
includes taxes & fees
26 Oct - 27 Oct
Luxury two floor apartment in prime location of famous Duval Street
A swimming pool with lounge chairs, palm trees, and a view of the sunset over the water.

7. One Bedroom Suite | Beachside Resort

One Bedroom Suite | Beachside Resort
Key West
10.0 out of 10, Exceptional, (7 reviews)
"Great property, room was amazing!"
United States
Daris Y.
The price is SAR 635
SAR 1,130 total
includes taxes & fees
27 Oct - 28 Oct
One Bedroom Suite | Beachside Resort
A clear swimming pool with lounge chairs and palm trees.

8. Slice of Paradise

Slice of Paradise
Stock Island
10.0 out of 10, Exceptional, (4 reviews)
"House was clean, what we expected, host responded promptly and accurately, pool was great."
United States
Cathy S.
Slice of Paradise
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

9. 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, (137 reviews)
"I can't say enough about how wonderful this property is or the host."
United States
Linda
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
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, (34 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 SAR 1,111
SAR 3,573 total
includes taxes & fees
15 Oct - 16 Oct
Southernmost Retreat | On Duval! With Hot Tub, Patio
A pool area with a hot tub, outdoor seating, and a wooden fence with pool rules posted.

11. Private Parking, Heated Pool - Sweet Caroline

Private Parking, Heated Pool - Sweet Caroline
Key West Historic District
9.0 out of 10, Wonderful, (32 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.
Private Parking, Heated Pool - Sweet Caroline
A wooden deck with two lounge chairs and a gazebo surrounded by lush greenery.

12. 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 SAR 1,798
SAR 3,610 total
includes taxes & fees
9 Nov - 10 Nov
Atlantis House Suites
A backyard with a swimming pool, wooden deck, and a covered patio area.

13. Conch Cove | Private Oasis with Heated Pool!

Conch Cove | Private Oasis with Heated Pool!
Old Town Key West
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful spot and outstanding property management company. "
United States
Jessica B.
Conch Cove | Private Oasis with Heated Pool!
A clear swimming pool surrounded by palm trees and lounge chairs, with a building in the background.

14. 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 SAR 1,014
SAR 2,226 total
includes taxes & fees
18 Oct - 19 Oct
Spacious 3-bedroom townhome on Stock Island with resort style pool.
A hallway with closed louvered doors, a wall-mounted light fixture, and a framed tropical-themed artwork.

15. Duval Vibes • Pool • 10 Guests

Duval Vibes • Pool • 10 Guests
Old Town Key West
10.0 out of 10, Exceptional, (17 reviews)
"Everything was clean and tidy, had trouble opening the door and the host was there to help with answering the questions I had. Super fun place to stay or even to relax"
United States
Grace K.
Duval Vibes • Pool • 10 Guests
A covered patio with a glass table and chairs, a pool, and a wooden deck.

16. Casa De Cubana | New! Cuban-Style Home Near Duval

Casa De Cubana | New! Cuban-Style Home Near Duval
Old Town Key West
10.0 out of 10, Exceptional, (41 reviews)
"This was a beutiful location and stay. "
United States
Jon-Paul G.
Casa De Cubana | New! Cuban-Style Home Near Duval
A white building with blue shutters, surrounded by lush greenery and a brick pathway.

17. Passover Cottage | Private Pool & Ideal Key West Location

Passover Cottage | Private Pool & Ideal Key West Location
Old Town Key West
10.0 out of 10, Exceptional, (20 reviews)
"We had the most amazing stay the house was perfect very clean lots of room big pool and large outdoor space and GREAT location. We will definitely return."
United States
Jennifer Y.
Passover Cottage | Private Pool & Ideal Key West Location
A bed with a white quilt and two pillows, one with a floral pattern. There are two wooden nightstands with lamps, and a painting on the wall.

18. Hemingway's Neighbor: Hot Tub, Sundeck, Old Town

Hemingway's Neighbor: Hot Tub, Sundeck, Old Town
Old Town Key West
9.8 out of 10, Exceptional, (18 reviews)
"Perfect location parking is a plus and being put friendly as a plus"
United States
Kat B.
Hemingway's Neighbor: Hot Tub, Sundeck, Old Town
A modern living space with a kitchen, a dining area, a seating area with a view of a pool, and a ceiling fan.

19. Keys Breeze - Walk to Duval, Private Pool

Keys Breeze - Walk to Duval, Private Pool
Old Town Key West
10.0 out of 10, Exceptional, (38 reviews)
"Great place, location, clean and climate controlled. Pool was great and the host was excellent!"
United States
Lisa S.
The price is SAR 7,838
SAR 11,696 total
includes taxes & fees
7 Nov - 8 Nov
Keys Breeze - Walk to Duval, Private Pool
A living room with a door, a window with blinds, a lamp, a sofa with patterned cushions, and a small table.

20. The Mesa House - One block from Duval St

The Mesa House - One block from Duval St
Key West Historic District
9.8 out of 10, Exceptional, (9 reviews)
"Perfect home for our family! The location was ideal for exploring Key West and enjoying the nightlife on Duval. The beds were comfortable and the kitchen had everything we needed. We will return!"
United States
Debbie P.
The price is SAR 2,535
SAR 5,556 total
includes taxes & fees
15 Oct - 16 Oct
The Mesa House - One block from Duval St
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Key West Hotel Reviews

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"The beach was not swimma"
Kamila 4-night trip
Posted 2 hours ago
Casa Marina Key West, Curio Collection by Hilton