Search Vacation Homes in Key West
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Key West vacation homes
1. Aug.-Sept. Special@119.lodging Only 119. + extras. From.8-17 to 9-30
Aug.-Sept. Special@119.lodging Only 119. + extras. From.8-17 to 9-30Old Town Key West
9.0 out of 10, Wonderful, (198 reviews)
"Fantastic location! Close enough to walk to all the things, but very quiet and relaxing to hang out. Loved the back deck.
Owner was very responsive and helpful.
Neighbors were nice as well."
Jeanine
The price is ￥17,067
￥45,816 total
includes taxes & fees
Aug 31 - Sep 1
2. 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
10.0 out of 10, Exceptional, (22 reviews)
"The property was very clean with an excellent location. "
Mike T.
The price is ￥24,191
￥74,082 total
includes taxes & fees
Aug 31 - Sep 1
3. Andros Suite | Perfect Location with Pool!
Andros Suite | Perfect Location with Pool!Old Town Key West
10.0 out of 10, Exceptional, (3 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 ￥24,177
￥74,199 total
includes taxes & fees
Sep 10 - Sep 11
4. Poolside Cottage #412
Poolside Cottage #412Key West
9.4 out of 10, Exceptional, (36 reviews)
"Very pleasant and generally a nice quiet community. "
Julia M.
The price is ￥26,533
￥48,077 total
includes taxes & fees
Sep 1 - Sep 2
5. Poolside Cottage #411
Poolside Cottage #411Key West
9.8 out of 10, Exceptional, (69 reviews)
"We stayed here for our honeymoon and it was perfect. The place was clean and well appointed. The pool right outside was huge and we spent lots of time there. Highly recommend!"
DeAnna Z.
The price is ￥26,518
￥47,094 total
includes taxes & fees
Sep 2 - Sep 3
6. Sea Esta Suite | Located On Iconic Duval w/ Pool
Sea Esta Suite | Located On Iconic Duval w/ PoolOld Town Key West
9.8 out of 10, Exceptional, (53 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
Rick H.
The price is ￥29,450
￥118,695 total
includes taxes & fees
Aug 31 - Sep 1
7. 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, (103 reviews)
"Great stay at a great location. Apartment was very clean. Enjoyed the balcony overlooking Duval St. "
Gregory L.
The price is ￥31,058
￥94,408 total
includes taxes & fees
Sep 9 - Sep 10
8. Casa Havana | Old Town Condo w/ Pool & Balcony
Casa Havana | Old Town Condo w/ Pool & BalconyOld Town Key West
9.0 out of 10, Wonderful, (6 reviews)
The price is ￥29,433
￥98,002 total
includes taxes & fees
Aug 30 - Aug 31
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.
Find vacation rentals that suit your style
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Key West Hotel Reviews
Southwinds Motel
8/10 Good
Find out more about Key West
Key West Vacation Homes information
Number of reviews | 828 |
|---|---|
Accommodation | 909 Vacation Homes |
Lowest Price | ￥44,019 |
Highest Price | ￥200,900 |
Explore a world of travel with Expedia
- Hotels near Florida Keys Eco - Discovery Center
- Casa Marina Hotels
- Cheap Hotels in Downtown Key West
- Resorts in Key Colony Beach
- Coral Lagoon Hotels
- Scuba Diving Hotels in Little Torch Key
- Hotels near South Beach
- Gay friendly Hotels in Key West
- Apartments in Key West
- Ranches in Key West
- Gay friendly Hotels in Key West Historic District
- Cheap Hotels in Lower Florida Keys
- Adults Only Resorts & in Key West
- Cheap Hotels in Old Town Key West
- Ryokans in Big Pine Key
- Hotels near Smathers Beach
- Beach Hotels in Downtown Key West
- Rv Parks in Bahia Honda Key
- Cheap Hotels in Casa Marina
- Scuba Diving Hotels in Downtown Key West
- Beach Hotels in Key Colony Beach
- Resorts in Stock Island
- Residences in Summerland Key
- Hotels near Calusa Beach
- Farmstay in Marathon
- Family Hotels in Grassy Key
- Apartments in Cow Key
- Aparthotels in Key Colony Beach
- Hotels near Simonton Beach
- Gay friendly Hotels in Old Town Key West
- Holiday Park Resorts in Key West
- Luxury Hotels in Casa Marina
- Resorts in Little Torch Key
- Hotels near Florida Keys Marathon
- Hotels near Fort Zachary Taylor Historic State Park
- Guest Houses in Key West
- Hotels near Sombrero Beach
- Luxury Hotels in Beachside
- All-Inclusive Hotel Hotels in Sunset Key
- Apartments in Big Pine Key
- Hotels near Key West Intl.
- Waterpark Hotels in Key West
- Key West Hotels
- Historic Hotels in Key West
- Luxury Hotels in Key West
- Hostels in Key West
- Cow Key Hotels
- Guest Houses in Cudjoe Key
- Marathon Hotels
- Resorts & Hotels with Spas in Beachside
- Beach Hotels in Key West
- Cheap Hotels in Key West Historic District
- Hotels near Ernest Hemingway Home and Museum
- Hotels near Florida Keys Beaches
- Adults Only Resorts & in Downtown Key West
- All-Inclusive Hotel Hotels in Key Colony Beach
- Vacation Homes in Big Pine Key
- All-Inclusive Hotel Hotels in Bahama Village
- Scuba Diving Hotels in Old Town Key West
- Hotels near Southernmost Point
- Hotels with a Pool in Key West
- Pet-Friendly Hotels in Key West
- Vacation Homes in Marathon
- Beach Hotels in Key West Historic District
- Cheap Hotels in Cudjoe Key
- Riads in Big Pine Key
- Rv Parks in Key West
- Cheap Hotels in Sugarloaf Key
- Romantic Hotels in Sugarloaf Key
- Condo Resorts in Key Colony Beach
- Beach Hotels in Midtown
- Hotels near Key West Naval Station
- Hotels near Harry S. Truman Little White House
- Cheap Hotels in Beachside
- Resorts in Key West
- Motels in Lower Florida Keys
- Inns in Key Colony Beach
- Scuba Diving Hotels in Key West
- Cheap Hotels in Key West
- Aparthotels in Key West
- Lodges in Key West
- Shopping Hotels in Sunset Key
- Resorts in No Name Key
- Adults Only Resorts & in Marathon
- Big Pine Key Hotels
- All-Inclusive Hotel Hotels in Downtown Key West
- Hotels near Duval Street
- Resorts & Hotels with Spas in Little Torch Key
- Hotels near Florida Keys National Marine Sanctuary
- Hotels near Key West Historic Seaport
- Resorts in Bahia Honda Key
- Family Hotels in Lower Keys
- Lodges in Big Pine Key
- Scuba Diving Hotels in Marathon
- All-Inclusive Hotel Hotels in Key West
- Palaces in Key Colony Beach