Holiday 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 holiday homes
Poolside Cottage #411
Poolside Cottage #411Key West
9.8 out of 10, Exceptional, (63 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 AU$454
includes taxes & fees
21 June - 22 June
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, (19 reviews)
"Definitely an adorable place to stay! The host was very accommodating with any questions we had, especially when our flight arrived earlier than planned. Great location for walking to Duval Street and many other great places. Our room was very small but we knew that before staying. Dont suggest this room for anyone over 5'7 ... lol. Still was perfect for us though. Clean, friendly staff, quiet. Would definitely stay here again."
Christin M.
The price is AU$423
includes taxes & fees
1 June - 2 June
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
9.8 out of 10, Exceptional, (14 reviews)
"The property was very clean with an excellent location. "
Mike T.
The price is AU$704
includes taxes & fees
14 June - 15 June
Paradise found
Paradise foundStock Island
9.8 out of 10, Exceptional, (37 reviews)
"Great house and location. We have found our rental for our yearly stay in Key West. "
Elizabeth F.
The price is AU$860
includes taxes & fees
2 June - 3 June
One Bedroom Suite | Beachside Resort
One Bedroom Suite | Beachside ResortKey West
10.0 out of 10, Exceptional, (2 reviews)
"Nice place to stay! Highly recommend!"
Mike C.
The price is AU$454
includes taxes & fees
31 May - 1 June
Poolside Cottage #412
Poolside Cottage #412Key West
9.4 out of 10, Exceptional, (31 reviews)
"Everything you need for a great stay!!"
Karen D.
The price is AU$454
includes taxes & fees
16 June - 17 June
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, (45 reviews)
"Great stay! "
Colleen S.
The price is AU$1,213
includes taxes & fees
16 June - 17 June
Casa Havana | Old Town Condo w/ Pool & Balcony
Casa Havana | Old Town Condo w/ Pool & BalconyOld Town Key West
8.6 out of 10, Excellent, (4 reviews)
"Wonderful location, clean, quiet. All around it was a great experience staying here!"
Kim T.
The price is AU$1,056
includes taxes & fees
1 June - 2 June
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 holiday rentals that suit your style
Private holiday homes
Condos
Save an average of 15% on thousands of hotels when you're signed in
Top Key West Hotel Reviews
Oceans Edge Key West Resort, Hotel & Marina
10/10 Excellent
Find out more about Key West
Key West Holiday Homes information
Number of reviews | 532 |
|---|---|
Accommodation | 890 Holiday Homes |
Lowest Price | AU$423 |
Highest Price | AU$1,895 |
Explore a world of travel with Expedia
- Luxury Hotels in Bahama Village
- Holiday Homes in Bahia Honda Key
- B&B in Big Pine Key
- Cabin Rentals in Big Pine Key
- Motels in Big Pine Key
- Ranches in Big Pine Key
- Town Houses in Boca Chica Key
- Casa Marina Hotels
- Motels in Cow Key
- Holiday Homes in Cudjoe Key
- Monroe County Hotels
- Beach Hotels in Downtown Key West
- Business Hotels in Downtown Key West
- Family Hotels in Downtown Key West
- Historic Hotels in Downtown Key West
- Hotels with Parking in Downtown Key West
- Luxury Hotels in Downtown Key West
- Dredgers Key Hotels
- Resort in Duck Key
- Hotels near Duval Street
- Hotels near Ernest Hemingway Home and Museum
- Caravan Parks in Flamingo
- Holiday Parks in Flamingo
- Resort in Flamingo
- Villas in Flamingo
- Fleming Key Hotels
- Hotels near Fort East Martello Museum and Gallery
- Hotels near Fort Zachary Taylor Historic State Park
- Resort in Grassy Key
- Historic Hotels in Historic Seaport
- Motels in Islamorada
- Resort in Islamorada
- Riads in Islamorada
- Villas in Islamorada
- Condo Rentals in Key Colony Beach
- Holiday Homes in Key Colony Beach
- Motels in Key Colony Beach
- All Inclusive Hotels in Key West Historic District
- Cheap Hotels in Key West Historic District
- Family Hotels in Key West Historic District
- Key West Historic District Hotels
- Hotels near Key West Historic Seaport
- Hotels near Key West Lighthouse and Keeper's Quarters Museum
- B&B in Lower Florida Keys
- Holiday Homes in Lower Florida Keys
- Cottages in Marathon
- Midtown Hotels
- New Town Hotels
- Holiday Homes in No Name Key
- Adults Only Hotels in Old Town Key West
- Beach Hotels in Old Town Key West
- Cheap Hotels in Old Town Key West
- Historic Hotels in Old Town Key West
- Luxury Hotels in Old Town Key West
- Old Town Key West Hotels
- Holiday Homes in Raccoon Key
- Hotels near Smathers Beach
- Hotels near Southernmost Point
- Hostels in Stock Island
- Hotels near Studios of Key West
- B&B in Sugarloaf Key
- Villas in Sugarloaf Key
- Condo Rentals in Summerland Key
- Boutique Hotels in Sunset Key
- Luxury Hotels in Sunset Key
- The Meadows Hotels
- Cheap Hotels in Truman Annex
- Truman Annex Hotels
- Flights to Dredgers Key
- Flights from Key West Intl.
- Flights from Cancun (CUN) to Key West (EYW)
- Flights from Dallas (DAL) to Key West (EYW)
- Flights from Washington (DCA) to Key West (EYW)
- Flights from Dallas (DFW) to Key West (EYW)
- Flights from Newark Liberty Intl. Airport (EWR) to Key West (EYW)
- Flights from Fort Lauderdale (FLL) to Key West (EYW)
- Flights from Genoa (GOA) to Key West (EYW)
- Flights from New York (JFK) to Key West (EYW)
- Flights from Los Angeles (LAX) to Key West (EYW)
- Flights from Orlando (MCO) to Key West (EYW)
- Flights from Melbourne (MEL) to Key West (EYW)
- Flights from Miami (MIA) to Key West (EYW)
- Flights from Melbourne (MLB) to Key West (EYW)
- Flights from Smyrna (MQY) to Key West (EYW)
- Flights from New Orleans (MSY) to Key West (EYW)
- Flights from Chicago (ORD) to Key West (EYW)
- Flights from Perth (PER) to Key West (EYW)
- Flights from San Francisco (SFO) to Key West (EYW)
- Flights from Sarasota (SRQ) to Key West (EYW)
- Flights from Sydney (SYD) to Key West (EYW)
- Flights from Tampa (TPA) to Key West (EYW)