Book Holiday Homes in Key West

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Featured Holiday Homes in Key West

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

Stock Island
Stay at this vacation home in Key West. Enjoy free WiFi, concierge services, and balconies. Popular attractions Duval Street and Mallory Square are located ...
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!

BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!

Key West
Stay at this vacation home in Key West. Enjoy free WiFi, private pools, and concierge services. Popular attractions Duval Street and Mallory Square are located ...
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

Key West
Stay at this vacation home in Key West. Enjoy free WiFi, a fitness center, and concierge services. Popular attractions Duval Street and Mallory Square are located ...
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
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ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!

ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!

Key West
Stay at this vacation home in Key West. Enjoy free WiFi, a garden, and concierge services. Popular attractions Duval Street and Mallory Square are located ...
ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

Stock Island
Stay at this vacation home in Key West. Enjoy free WiFi, concierge services, and patios. Popular attractions Duval Street and Mallory Square are located ...
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL

PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL

Key West
Stay at this vacation home in Key West. Enjoy free WiFi, private pools, and concierge services. Popular attractions Duval Street and Mallory Square are located ...
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK

Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK

Key West
Stay at this vacation home in Key West. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Duval Street and Mallory Square ...
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
Poolside Cottage #411

Poolside Cottage #411

Key West
Stay at this vacation home in Key West. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Duval Street and Mallory Square are located ...
Poolside Cottage #411
Poolside Cottage #412

Poolside Cottage #412

Key West
Stay at this vacation home in Key West. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Duval Street and Mallory Square are located ...
Poolside Cottage #412
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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
815 Holiday Homes
Lowest Price
NZ$351
Highest Price
NZ$580
Popular accommodation
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!, BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!, OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!, ISLAND DAZE ~ Perfectly Located 2 Bedroom, 2 Bathroom Cottage!, ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!, PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL , Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK, Poolside Cottage #411, Poolside Cottage #412

Top trending hotels in Key West

Southernmost Beach Resort

Southernmost Beach Resort

4 out of 5
1319 Duval Street, Key West, FL
Fully refundableReserve now, pay when you stay
The price is NZ$580 per night from 17 Dec to 18 Dec
NZ$580
includes taxes & fees
17 Dec - 18 Dec
Stay at this 4-star beach hotel in Key West. Enjoy 3 outdoor pools, a full-service spa, and a beach locale. Our guests praise the pool and the bar in our reviews. ...
Southernmost Beach Resort
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
The price is NZ$497 per night from 19 Dec to 20 Dec
NZ$497
includes taxes & fees
19 Dec - 20 Dec
Stay at this 4-star beach hotel in Key West. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant ...
Margaritaville Beach House Key West
Havana Cabana at Key West - Adults Only

Havana Cabana at Key West - Adults Only

4 out of 5
3420 N. Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is NZ$417 per night from 9 Dec to 10 Dec
NZ$417
includes taxes & fees
9 Dec - 10 Dec
Stay at this 4-star business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the bar in ...
Havana Cabana at Key West - Adults Only
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Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is NZ$351 per night from 24 Nov to 25 Nov
NZ$351
includes taxes & fees
24 Nov - 25 Nov
Stay at this 3.5-star beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
Beachside Resort & Residences
Don't see what you're looking for?
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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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^Subject to availability and chosen travel dates.