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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Fleming Key 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, (38 reviews)
"Wonderful stay. Thank you."
United States
shannon b.
The price is SAR 694
SAR 1,180 total
includes taxes & fees
1 Dec - 2 Dec
Poolside Cottage #412
A building with a red door, a covered porch, and a bamboo plant in the foreground.

2. 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)
"Excellent property and the communication with the hosts was excellent. Love that they offered complimentary pickup from the airport to the property too."
United States
Mike C.
The price is SAR 552
SAR 1,641 total
includes taxes & fees
16 Dec - 17 Dec
Road's End | Prime Old Town Location! Updated Home w/ Pool
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

3. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (72 reviews)
"Excellent cottage in a quiet location. Our family of 4 enjoyed the stay & plan to return in the future!"
United States
Jennifer W.
The price is SAR 694
SAR 1,180 total
includes taxes & fees
1 Dec - 2 Dec
Poolside Cottage #411
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with bar stools.

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

Sea Esta Suite | Located On Iconic Duval w/ Pool
Old Town Key West
9.6 out of 10, Exceptional, (59 reviews)
"Really enjoyed our stay and the location was convenient to Duval Street and all that it has to offer."
United States
DeEtta H.
The price is SAR 729
SAR 2,720 total
includes taxes & fees
16 Nov - 17 Nov
Sea Esta Suite | Located On Iconic Duval w/ Pool
A porch with wooden chairs and a table, a wooden door with green shutters, and a white railing.

5. 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 SAR 342
SAR 1,124 total
includes taxes & fees
17 Nov - 18 Nov
Shared Pool & Near Duval - Curry House Room 9
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 725
SAR 2,714 total
includes taxes & fees
16 Nov - 17 Nov
Casa Havana | Old Town Condo w/ Pool & Balcony
A patio area with a fountain, seating, and umbrellas.

7. Andros Suite | Perfect Location with Pool!

Andros Suite | Perfect Location with Pool!
Old Town Key West
10.0 out of 10, Exceptional, (6 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 552
SAR 1,645 total
includes taxes & fees
30 Nov - 1 Dec
Andros Suite | Perfect Location with Pool!
A wooden deck with two lounge chairs and a gazebo surrounded by lush greenery.

8. Atlantis House Suites

Atlantis House Suites
Midtown
10.0 out of 10, Exceptional, (4 reviews)
"This space had everything you need just out of the hustle and bustle but close enough to join in. The beds were very comfortable & hosts responded to all our questions quickly. Great outdoor space as well! We will be back!"
United States
Julie C.
The price is SAR 871
SAR 2,432 total
includes taxes & fees
17 Nov - 18 Nov
Atlantis House Suites
A spacious living room with a large L-shaped sectional sofa, a round coffee table, and a staircase leading to an upper level.

9. Evershore Estate at Lunara Bay | Wellness Home

Evershore Estate at Lunara Bay | Wellness Home
Raccoon Key
10.0 out of 10, Exceptional, (31 reviews)
"The house is perfect for our family. Access to water, pool and close enough to key west!"
United States
John F.
The price is SAR 2,248
SAR 5,467 total
includes taxes & fees
24 Nov - 25 Nov
Evershore Estate at Lunara Bay | Wellness Home
A clear swimming pool with lounge chairs and palm trees.

10. 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 SAR 976
SAR 2,093 total
includes taxes & fees
17 Nov - 18 Nov
Slice of Paradise
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a building in the background.

11. Gone Coastal

Gone Coastal
Stock Island
9.6 out of 10, Exceptional, (22 reviews)
"Great place , clean and close to everything!"
United States
april
The price is SAR 1,010
SAR 2,045 total
includes taxes & fees
7 Dec - 8 Dec
Gone Coastal
A living room with a beige sofa, a white coffee table with a plant, and a view through glass doors to an outdoor area.

12. Waterlane House at Lunara Bay

Waterlane House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (38 reviews)
"Everything was great"
United States
Justin S.
The price is SAR 3,246
SAR 6,729 total
includes taxes & fees
18 Nov - 19 Nov
Waterlane House at Lunara Bay
A pool area with lounge chairs and umbrellas, a covered deck, and a house with a balcony.

13. Mirador House at Lunara Bay

Mirador House at Lunara Bay
Raccoon Key
9.6 out of 10, Exceptional, (38 reviews)
"Very nice property"
United States
Jared G.
The price is SAR 2,248
SAR 6,108 total
includes taxes & fees
25 Nov - 26 Nov
Mirador House at Lunara Bay
A spacious foyer with a wooden staircase, a console table with decorative items, and a view of the outdoors through a glass door.

14. Evershore House Pool Parking Dock

Evershore House Pool Parking Dock
2.0 star property
Raccoon Key
The price is SAR 2,883
SAR 5,844 total
includes taxes & fees
24 Nov - 25 Nov
Evershore House Pool Parking Dock
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

15. 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, (140 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 SAR 996
SAR 2,213 total
includes taxes & fees
19 Nov - 20 Nov
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A modern kitchen with a central island, wicker chairs, and pendant lighting.

16. The Shellstone House at Solaire Lunara Bay

The Shellstone House at Solaire Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (7 reviews)
"Great property / location. Perfect house with wonderful amenities!!!"
United States
Dudley S.
The price is SAR 6,688
SAR 12,279 total
includes taxes & fees
30 Nov - 1 Dec
The Shellstone House at Solaire Lunara Bay
A wooden deck with a hanging hammock and a view of a green landscape.

17. Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"This place was everything we needed. The location was the perfect combination of secluded but with accessibility to Marathon and Key West. The house had everything we needed. We loved the appliances, the bed, the shower and the wrap-around porch with the swing. And the people managing the property made our visit the best experience from booking to departure. Will book again!"
United States
Tom H.
The price is SAR 889
SAR 2,410 total
includes taxes & fees
19 Nov - 20 Nov
Starlight Serenity - Hideaway with Stunning Views
An aerial view of a beach with clear turquoise waters, a sandy shore, and a dense forested area.

18. 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, (105 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
Pool Deck with Lounge Chairs

19. The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (31 reviews)
"Great property, terrific hosts - amazing location!"
United States
Jason T.
The price is SAR 3,096
SAR 6,541 total
includes taxes & fees
17 Nov - 18 Nov
The Seagate Estate at Lunara Bay
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, (9 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 963
SAR 2,166 total
includes taxes & fees
16 Nov - 17 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.
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