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Our top choices for Key West vacation homes
1. Road's End | Prime Old Town Location! Updated Home w/ Pool
Road's End | Prime Old Town Location! Updated Home w/ PoolOld 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."
Mike C.
The price is AED 541
AED 1,606 total
includes taxes & fees
15 Nov - 16 Nov
2. 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!"
Robert J.
The price is AED 545
AED 1,615 total
includes taxes & fees
30 Nov - 1 Dec
3. Shared Pool & Near Duval - Curry House Room 9
Shared Pool & Near Duval - Curry House Room 9Old Town Key West
7.4 out of 10, Good, (20 reviews)
"Nice and clean.Quiet and convenient to Duval.We will be back!"
Deborah L.
The price is AED 367
AED 1,141 total
includes taxes & fees
18 Nov - 19 Nov
4. Poolside Cottage #411
Poolside Cottage #411Key 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!"
Jennifer W.
The price is AED 680
AED 1,148 total
includes taxes & fees
1 Dec - 2 Dec
5. Poolside Cottage #412
Poolside Cottage #412Key West
9.4 out of 10, Exceptional, (38 reviews)
"Wonderful stay. Thank you."
shannon b.
The price is AED 680
AED 1,148 total
includes taxes & fees
1 Dec - 2 Dec
6. Casa Havana | Old Town Condo w/ Pool & Balcony
Casa Havana | Old Town Condo w/ Pool & BalconyOld Town Key West
9.2 out of 10, Wonderful, (12 reviews)
"Wonderful location, clean, quiet. All around it was a great experience staying here!"
Kim T.
The price is AED 714
AED 2,662 total
includes taxes & fees
16 Nov - 17 Nov
7. Sea Esta Suite | Located On Iconic Duval w/ Pool
Sea Esta Suite | Located On Iconic Duval w/ PoolOld Town Key West
9.6 out of 10, Exceptional, (59 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
Rick H.
The price is AED 710
AED 2,649 total
includes taxes & fees
11 Nov - 12 Nov
8. Shared Pool & Parking - The Cottage at James House
Shared Pool & Parking - The Cottage at James HouseKey West Historic District
8.6 out of 10, Excellent, (10 reviews)
"Awesome location! "
Lindsey M.
The price is AED 1,168
AED 1,948 total
includes taxes & fees
30 Nov - 1 Dec
9. Luxury two floor apartment in prime location of famous Duval Street
Luxury two floor apartment in prime location of famous Duval StreetOld 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. "
Gregory L.
The price is AED 1,084
AED 2,653 total
includes taxes & fees
16 Nov - 17 Nov
10. Slice of Paradise
Slice of ParadiseStock Island
10.0 out of 10, Exceptional, (5 reviews)
"House was clean, what we expected, host responded promptly and accurately, pool was great."
Cathy S.
The price is AED 955
AED 2,033 total
includes taxes & fees
10 Nov - 11 Nov
11. Southernmost Retreat | On Duval! With Hot Tub, Patio
Southernmost Retreat | On Duval! With Hot Tub, PatioOld Town Key West
9.6 out of 10, Exceptional, (35 reviews)
"Awesome place great location communication with host was great would stay here again next time I’m in key west."
Drew L.
The price is AED 1,191
AED 3,476 total
includes taxes & fees
6 Dec - 7 Dec
12. Coconut Palm by Brightwild Island Home w Pool
Coconut Palm by Brightwild Island Home w PoolOld Town Key West
The price is AED 2,068
AED 4,039 total
includes taxes & fees
30 Nov - 1 Dec
13. Coconut Palm - Steps from Duval with Private Pool
Coconut Palm - Steps from Duval with Private PoolOld Town Key West
9.0 out of 10, Wonderful, (40 reviews)
"Great Property Excellent location "
Jim B.
The price is AED 1,612
AED 3,747 total
includes taxes & fees
30 Nov - 1 Dec
14. 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 CHAIRSStock Island
9.6 out of 10, Exceptional, (139 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!"
Melanie K.
The price is AED 1,091
AED 2,300 total
includes taxes & fees
10 Nov - 11 Nov
15. Poolside Paradise
Poolside ParadiseStock Island
The price is AED 1,319
AED 2,524 total
includes taxes & fees
30 Nov - 1 Dec
16. Keys Breeze - Walk to Duval, Private Pool
Keys Breeze - Walk to Duval, Private PoolOld Town Key West
9.8 out of 10, Exceptional, (41 reviews)
"Great place, location, clean and climate controlled. Pool was great and the host was excellent!"
Lisa S.
The price is AED 2,806
AED 5,395 total
includes taxes & fees
30 Nov - 1 Dec
17. Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval StOld Town Key West
9.4 out of 10, Exceptional, (58 reviews)
"Great location and we would stay here again. "
Brandon A.
The price is AED 1,837
AED 4,167 total
includes taxes & fees
30 Nov - 1 Dec
18. Atlantis House Suites
Atlantis House SuitesMidtown
10.0 out of 10, Exceptional, (3 reviews)
"Awesome place to stay ! Located just close enough and just far away enough . Highly recommended "
Aaron J.
The price is AED 1,314
AED 2,913 total
includes taxes & fees
15 Nov - 16 Nov
19. Conch Cove | Private Oasis with Heated Pool!
Conch Cove | Private Oasis with Heated Pool!Old Town Key West
9.8 out of 10, Exceptional, (44 reviews)
"Wonderful spot and outstanding property management company. "
Jessica B.
The price is AED 1,647
AED 4,378 total
includes taxes & fees
30 Nov - 1 Dec
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. "
Samantha P.
The price is AED 992
AED 2,179 total
includes taxes & fees
23 Nov - 24 Nov
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.
Learn more about Key West
Stroll Duval Street's colorful shops and bars before catching the sunset celebration at Mallory Square with local performers. Explore Hemingway's historic home where six-toed cats roam freely, then snorkel the vibrant coral reefs just offshore.
