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 patio area with a fountain, seating, and umbrellas.

1. 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.
Andros Suite | Perfect Location with 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 1,128 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.

3. 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 714
SAR 2,813 total
includes taxes & fees
29 Oct - 30 Oct
Sea Esta Suite | Located On Iconic Duval w/ 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.
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.
One Bedroom Suite | Beachside Resort
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 1,107
SAR 2,699 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 and a thatched roof structure, surrounded by lush greenery and a brick patio.

7. 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 patio area with wicker furniture and a grill.

8. 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 3,529 total
includes taxes & fees
20 Oct - 21 Oct
Southernmost Retreat | On Duval! With Hot Tub, Patio
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, (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 2,122 total
includes taxes & fees
20 Oct - 21 Oct
Slice of Paradise
A covered porch with a table and chairs, a view of the street, and a building with a balcony.

10. 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.
Casa Havana | Old Town Condo w/ Pool & Balcony
A clear swimming pool surrounded by palm trees and lounge chairs, with a building in the background.

11. 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 2,224 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.

12. 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 1,767
SAR 4,719 total
includes taxes & fees
30 Oct - 31 Oct
Conch Cove | Private Oasis with Heated Pool!
A living room with a ceiling fan, a TV mounted on the wall, and a sofa.

13. Poolside Paradise

Poolside Paradise
Stock Island
The price is SAR 1,111
SAR 2,414 total
includes taxes & fees
18 Oct - 19 Oct
Poolside Paradise
A covered patio with a glass table and chairs, a pool, and a wooden deck.

14. 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 backyard with a swimming pool, lounge chairs, and a wooden fence.

15. 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 1,677
SAR 3,843 total
includes taxes & fees
17 Nov - 18 Nov
Coconut Palm - Steps from Duval with Private Pool
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.
The price is SAR 1,569
SAR 3,520 total
includes taxes & fees
31 Oct - 1 Nov
Passover Cottage | Private Pool & Ideal Key West Location
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.
Private Parking, Heated Pool - Sweet Caroline
A balcony with white railings, palm trees, and a view of a street with parked cars and buildings.

18. 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 1,501
SAR 3,805 total
includes taxes & fees
8 Nov - 9 Nov
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
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, (39 reviews)
"Great place, location, clean and climate controlled. Pool was great and the host was excellent!"
United States
Lisa S.
The price is SAR 2,927
SAR 5,587 total
includes taxes & fees
16 Nov - 17 Nov
Keys Breeze - Walk to Duval, Private Pool
A white two-story house with a balcony and a swimming pool.

20. Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (1 review)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is SAR 2,883
SAR 5,844 total
includes taxes & fees
26 Oct - 27 Oct
Capmar House by Brightwild Huge Home 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

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"The property was well maintained and clean. The tropical plants and trees were beautiful and made it feel like a little oasis. Our room was clean and we had what we needed. The staff we interacted with were very friendly and welcoming. Breakfast was good and was just enough to get the day started. We enjoyed the bar and the pools and the welcome drink was a nice treat! Overall we had a great experience and we would recommend this place for the amenities and the location."
Jason 4-night trip
Posted 4 hours ago
Winslow's Bungalows - Key West Historic Inns