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

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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 residential building with a white door, beige siding, and a small porch area with potted plants and a small tree.

1. 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 727
SAR 2,833 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.

2. 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 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 1,688 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 swimming pool with lounge chairs, palm trees, and a view of the sunset over the water.

5. One Bedroom Suite | Beachside Resort

One Bedroom Suite | Beachside Resort
Key West
10.0 out of 10, Exceptional, (8 reviews)
"Great property, room was amazing!"
United States
Daris Y.
The price is SAR 634
SAR 1,130 total
includes taxes & fees
27 Oct - 28 Oct
One Bedroom Suite | Beachside Resort
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

6. 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 794
SAR 1,948 total
includes taxes & fees
18 Oct - 19 Oct
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A clear swimming pool with lounge chairs and palm trees.

7. 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 943
SAR 2,123 total
includes taxes & fees
20 Oct - 21 Oct
Slice of Paradise
An aerial view of a beach with clear turquoise waters, a sandy shore, and a dense forested area.

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 1,107
SAR 2,711 total
includes taxes & fees
16 Nov - 17 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 1,111
SAR 3,556 total
includes taxes & fees
29 Oct - 30 Oct
Southernmost Retreat | On Duval! With Hot Tub, Patio
A pool area with a tiled deck, a wooden fence, and a staircase leading to a covered porch.

10. Sweet Caroline by Brightwild Pool Parking

Sweet Caroline by Brightwild Pool Parking
2.0 star property
Key West Historic District
The price is SAR 2,281
SAR 3,867 total
includes taxes & fees
27 Oct - 28 Oct
Sweet Caroline by Brightwild Pool Parking
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, (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 1,779
SAR 3,539 total
includes taxes & fees
27 Oct - 28 Oct
Private Parking, Heated Pool - Sweet Caroline
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 1,014
SAR 2,225 total
includes taxes & fees
18 Oct - 19 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, (42 reviews)
"Wonderful spot and outstanding property management company. "
United States
Jessica B.
The price is SAR 1,611
SAR 4,523 total
includes taxes & fees
29 Oct - 30 Oct
Conch Cove | Private Oasis with Heated Pool!
A backyard with a swimming pool, lounge chairs, and a wooden fence.

14. 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 1,945
SAR 4,171 total
includes taxes & fees
27 Oct - 28 Oct
Coconut Palm - Steps from Duval with Private Pool
A covered patio with a glass table and chairs, a pool, and a wooden deck.

15. 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.

16. 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.
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.

17. 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 1,502
SAR 3,807 total
includes taxes & fees
8 Nov - 9 Nov
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
A living room with a ceiling fan, a TV mounted on the wall, and a sofa.

18. Poolside Paradise

Poolside Paradise
Stock Island
Poolside Paradise
A modern kitchen with white cabinetry, a large island with stools, a built-in oven, and a stainless steel refrigerator.

19. 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.
Luxurious Island Pearl-Private Pool - 2BD/2Bath
A covered outdoor patio with a pool, seating area, and lush greenery.

20. 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 2,451
SAR 4,507 total
includes taxes & fees
27 Oct - 28 Oct
Coconut Palm by Brightwild Island Home w 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.
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Top Key West Hotel Reviews

The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

10/10 Excellent
"We enjoyed the King Suite. Especially the modern updated ensuite. The pool and hot tub were fantastic in a unique private setting with ample palm trees and greenery."
Camiel 3-night trip
Posted 1 hour ago
The Southernmost Inn - Adults Only