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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Key West vacation 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, (26 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 SAR 640
SAR 1,834 total
includes taxes & fees
15 Nov - 16 Nov
Road's End | Prime Old Town Location! Updated Home w/ Pool
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, (56 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
United States
Rick H.
The price is SAR 693
SAR 2,779 total
includes taxes & fees
29 Oct - 30 Oct
Sea Esta Suite | Located On Iconic Duval w/ Pool
A wooden deck with a large tree, outdoor seating, and a marina in the background.

3. 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 1,135 total
includes taxes & fees
25 Oct - 26 Oct
Poolside Cottage #412
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 1,117 total
includes taxes & fees
29 Oct - 30 Oct
Poolside Cottage #411
A patio area with a fountain, seating, and umbrellas.

5. 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 532
SAR 1,694 total
includes taxes & fees
2 Nov - 3 Nov
Andros Suite | Perfect Location with Pool!
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 SAR 1,027
SAR 2,778 total
includes taxes & fees
15 Nov - 16 Nov
Casa Havana | Old Town Condo w/ Pool & Balcony
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, (9 reviews)
"Great property, room was amazing!"
United States
Daris Y.
The price is SAR 664
SAR 1,162 total
includes taxes & fees
25 Oct - 26 Oct
One Bedroom Suite | Beachside Resort
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, (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 1,857
SAR 3,648 total
includes taxes & fees
14 Nov - 15 Nov
Luxury two floor apartment in prime location of famous Duval Street
A patio area with wicker furniture and a grill.

9. 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 1,110
SAR 3,553 total
includes taxes & fees
29 Oct - 30 Oct
Southernmost Retreat | On Duval! With Hot Tub, Patio
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

10. 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
The price is SAR 979
SAR 2,178 total
includes taxes & fees
26 Oct - 27 Oct
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A clear swimming pool with lounge chairs and palm trees.

11. 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.
The price is SAR 942
SAR 2,133 total
includes taxes & fees
26 Oct - 27 Oct
Slice of Paradise
A clear swimming pool surrounded by palm trees and lounge chairs, with a building in the background.

12. 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 1,013
SAR 2,208 total
includes taxes & fees
25 Oct - 26 Oct
Spacious 3-bedroom townhome on Stock Island with resort style pool.
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, (43 reviews)
"Wonderful spot and outstanding property management company. "
United States
Jessica B.
The price is SAR 1,609
SAR 4,542 total
includes taxes & fees
25 Oct - 26 Oct
Conch Cove | Private Oasis with Heated Pool!
A bathroom with a toilet, a sink, and a towel rack with a towel.

14. Poolside Paradise

Poolside Paradise
Stock Island
The price is SAR 1,111
SAR 2,409 total
includes taxes & fees
30 Oct - 31 Oct
Poolside Paradise
A covered outdoor patio with a pool, seating area, and lush greenery.

15. 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 SAR 2,124
SAR 4,138 total
includes taxes & fees
17 Nov - 18 Nov
Coconut Palm by Brightwild Island Home w Pool
A backyard with a swimming pool, lounge chairs, and a wooden fence.

16. 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 SAR 1,654
SAR 3,858 total
includes taxes & fees
17 Nov - 18 Nov
Coconut Palm - Steps from Duval with Private Pool
A pool area with a hot tub, outdoor seating, and a wooden fence with pool rules posted.

17. 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 SAR 1,635
SAR 3,361 total
includes taxes & fees
27 Oct - 28 Oct
Private Parking, Heated Pool - Sweet Caroline
A white building with blue shutters, surrounded by lush greenery and a brick pathway.

18. 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, (21 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.
The price is SAR 1,560
SAR 3,508 total
includes taxes & fees
30 Oct - 31 Oct
Passover Cottage | Private Pool & Ideal Key West Location
A balcony with white railings, palm trees, and a view of a street with parked cars and buildings.

19. 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, (56 reviews)
"Great location and we would stay here again. "
United States
Brandon A.
The price is SAR 1,500
SAR 3,804 total
includes taxes & fees
8 Nov - 9 Nov
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
A modern kitchen with white cabinetry, a large island with stools, a built-in oven, and a stainless steel refrigerator.

20. Luxurious Island Pearl-Private Pool - 2BD/2Bath

Luxurious Island Pearl-Private Pool - 2BD/2Bath
Key West Historic District
10.0 out of 10, Exceptional, (63 reviews)
"Excellent property and location!"
United States
Mark B.
The price is SAR 2,566
SAR 4,816 total
includes taxes & fees
2 Nov - 3 Nov
Luxurious Island Pearl-Private Pool - 2BD/2Bath
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
"All I can say is all aspects were fantastic"
Joseph 3-night trip
Posted 1 hour ago
Casa Marina Key West, Curio Collection by Hilton