Book Holiday Homes in Key West
More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)
We keep it easy with the option to pay now or later on select accommodation
Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Key West
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
Key West FL
With a stay at this vacation home, you'll be centrally located in Key West, steps from Duval Street and 10 minutes by foot from Florida Keys Beaches.
Key West Dreamin' - Private Pool Steps Off Duval
Key West FL
With a stay at this vacation home, you'll be centrally located in Key West, steps from Duval Street and 5 minutes by foot from South Beach.
Perfect Location, Private Heated Pool, Pristine Luxury Home!
Key West FL
The price is AU$3,725 per night from 21 Apr to 22 Apr
AU$3,725
21 Apr - 22 Apr
includes taxes & fees
A stay at this vacation home places you in the heart of Key West, steps from Duval Street and Ernest Hemingway Home and Museum.
Save an average of 15% on thousands of hotels when you're signed in
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
Key West FL
A stay at this vacation home places you in the heart of Key West, within a 10-minute walk of Duval Street and Ernest Hemingway Home and Museum.
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
Stock Island FL
When you stay at this vacation home in Key West, you'll be on the waterfront, within a 15-minute drive of Florida Keys Beaches and Duval Street.
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Stock Island FL
When you stay at this vacation home in Key West, you'll be on the waterfront, within a 10-minute drive of Smathers Beach and Florida Keys Beaches.
Key West Caribbean Cottage - On Duval St w Private Pool
Key West FL
With a stay at this vacation home, you'll be centrally located in Key West, steps from Duval Street and 5 minutes by foot from Ernest Hemingway Home and ...
Road's End | Prime Old Town Location! Updated Home w/ Pool
Key West FL
The price is AU$850 per night from 10 Apr to 11 Apr
AU$850
10 Apr - 11 Apr
includes taxes & fees
With a stay at this vacation home in Key West (Old Town Key West), you'll be steps from Duval Street and 4 minutes by foot from Ernest Hemingway Home and ...
LADY ADMIRAL ~Sweet cottage & guest house with private heated pool off Duval!
Key West FL
With a stay at this vacation home, you'll be centrally located in Key West, steps from Duval Street and 4 minutes by foot from South Beach.
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.
Key West Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Key West vacation homes are the perfect way for you to wing it.
Holiday houses in Key West let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Key West in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Key West adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Key West with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Key West vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Key West Holiday Homes essential information
Accommodation | 902 Holiday Homes |
|---|---|
Lowest Price | AU$427 |
Highest Price | AU$3,725 |
Popular accommodation | BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!, Key West Dreamin' - Private Pool Steps Off Duval, Perfect Location, Private Heated Pool, Pristine Luxury Home!, **THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES..., HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!, INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!, Key West Caribbean Cottage - On Duval St w Private Pool, Road's End | Prime Old Town Location! Updated Home w/ Pool, LADY ADMIRAL ~Sweet cottage & guest house with private heated pool off Duval! |
Top trending hotels in Key West
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is AU$477 per night from 5 May to 6 May
AU$477
5 May - 6 May
includes taxes & fees
A stay at Blue Flamingo Resort Key West places you in the heart of Key West, within a 10-minute drive of Stock Island Yacht Club & Marina and Key West Lighthouse ...
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
The price is AU$641 per night from 6 May to 7 May
AU$641
6 May - 7 May
includes taxes & fees
With a stay at Southernmost Beach Resort and Guesthouses, you'll be centrally located in Key West, steps from South Beach and within a 5-minute walk of Southernmost ...
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is AU$489 per night from 6 May to 7 May
AU$489
6 May - 7 May
includes taxes & fees
Located in Key West, Margaritaville Beach House Key West is by the ocean, a 4-minute drive from Fort East Martello Museum and Gallery and 6 minutes from Smathers ...
Save an average of 15% on thousands of hotels when you're signed in
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is AU$427 per night from 6 Apr to 7 Apr
AU$427
6 Apr - 7 Apr
includes taxes & fees
When you stay at Beachside Resort & Residences in Key West, you'll be next to a golf course, a 5-minute drive from Smathers Beach and 6 minutes from Florida ...
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.
More ways to explore Key West
Top Picks
- Cow Key Hotels
- Houseboats in Cow Key
- Cudjoe Gardens Hotels
- Hotels near Duval Street
- Aparthotels in Key West
- Apartments in Key West
- B&B in Key West
- Caravan Parks in Key West
- Condominium Resort in Key West
- Condo Rentals in Key West
- Guest Houses in Key West
- Boutique Hotels in Key West Historic District
- Key West Historic District Hotels
- Beach Hotels in Key West
- Boutique Hotels in Key West
- Ski Hotels in Key West
- Key West Hotels
- Houseboats in Key West
- Ryokans in Key West
- Midtown Hotels
- Old Town Key West Hotels
- Resorts in Ramrod Key
- Apartment Hotels in Stock Island
- Luxury Hotels in Stock Island
- Houseboats in Stock Island
- Caravan Parks in Sugarloaf Key
- Beach Hotels in Sugarloaf Key
- Hotels with Pool in Sugarloaf Key
- Sugarloaf Shores Hotels
- B&B in Summerland Key
- Summerland Key Hotels
- Motels in Summerland Key
- The Meadows Hotels
- Uptown - Upper Duval Hotels
- White St. Gallery Hotels
- White Street Gallery District Hotels
- Flights to Key West
- Flights to Sugarloaf Key
- Flights from Key West Intl.
- Flights from Adelaide (ADL) to Key West (EYW)
- Flights from Armidale (ARM) to Key West (EYW)
- Flights from Alice Springs (ASP) to Key West (EYW)
- Flights from Melbourne (AVV) to Key West (EYW)
- Flights from St. George's (BDA) to Key West (EYW)
- Flights from Brisbane (BNE) to Key West (EYW)
- Flights from Ballina (BNK) to Key West (EYW)
- Flights from Busselton (BQB) to Key West (EYW)
- Flights from Canberra (CBR) to Key West (EYW)
- Flights from Ceduna (CED) to Key West (EYW)
- Flights from Coffs Harbour (CFS) to Key West (EYW)
- Flights from Chattanooga (CHA) to Key West (EYW)
- Flights from Cairns (CNS) to Key West (EYW)
- Flights from Dallas (DAL) to Key West (EYW)
- Flights from Dubbo (DBO) to Key West (EYW)
- Flights from Washington (DCA) to Key West (EYW)
- Flights from Esperance (EPR) to Key West (EYW)
- Flights from Evansville (EVV) to Key West (EYW)
- Flights from Kalispell (FCA) to Key West (EYW)
- Flights from Gladstone (GLT) to Key West (EYW)
- Flights from Gainesville (GNV) to Key West (EYW)
- Flights from Hobart (HBA) to Key West (EYW)
- Flights from Horn Island (HID) to Key West (EYW)
- Flights from New York (JFK) to Key West (EYW)
- Flights from Kangaroo Island (KGC) to Key West (EYW)
- Flights from Lord Howe Island (LDH) to Key West (EYW)
- Flights from Kansas City (MCI) to Key West (EYW)
- Flights from McArthur River (MCV) to Key West (EYW)
- Flights from Melbourne (MEL) to Key West (EYW)
- Flights from Miami (MIA) to Key West (EYW)
- Flights from Mackay (MKY) to Key West (EYW)
- Flights from Morristown (MMU) to Key West (EYW)
- Flights from Minneapolis (MSP) to Key West (EYW)
- Flights from Moruya (MYA) to Key West (EYW)
- Flights from Newcastle (NTL) to Key West (EYW)
- Flights from Olympic Dam (OLP) to Key West (EYW)
- Flights from Cooma (OOM) to Key West (EYW)
- Flights from Perth (PER) to Key West (EYW)
- Flights from St. Petersburg (PIE) to Key West (EYW)
- Flights from Parkes (PKE) to Key West (EYW)
- Flights from Port Macquarie (PQQ) to Key West (EYW)
- Flights from Seattle (SEA) to Key West (EYW)
- Flights from Brunswick (SSI) to Key West (EYW)
- Flights from Sydney (SYD) to Key West (EYW)
- Flights from Tamworth (TMW) to Key West (EYW)
- Flights from Townsville (TSV) to Key West (EYW)
- Flights from Vero Beach (VRB) to Key West (EYW)
- Flights from Christmas Island (XCH) to Key West (EYW)
- Flights from Rouyn-Noranda (YUY) to Key West (EYW)
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.