Book Holiday Homes in Key West

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Featured Holiday Homes in Key West

DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!

DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!

Key West
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 ...
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

Key West
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 Ernest Hemingway Home and ...
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
Spec.Feb.24-Mar 1 @229+
w. 3 night stay close beach

Spec.Feb.24-Mar 1 @229+ w. 3 night stay close beach

Key West
A stay at this vacation home places you in the heart of Key West, within a 15-minute walk of Duval Street and Florida Keys Beaches.
Spec.Feb.24-Mar 1 @229+ w. 3 night stay close beach
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Feb 3-10
$245 off the rates
close beach full kitchen & patio

Feb 3-10 $245 off the rates close beach full kitchen & patio

Key West, FL
A stay at this vacation home places you in the heart of Key West, within a 15-minute walk of Duval Street and Florida Keys Beaches.
Feb 3-10 $245 off the rates close beach full kitchen & patio
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

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

Stock Island
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.
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Captain's Daughter: Oversized home for the whole family w/private pool & dock

Captain's Daughter: Oversized home for the whole family w/private pool & dock

Key West
With a stay at this vacation home in Key West (Meadows), you'll be within a 5-minute drive of Duval Street and Florida Keys Beaches.
Captain's Daughter: Oversized home for the whole family w/private pool & dock
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!

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

Key West
With a stay at this vacation home, you'll be centrally located in Key West, steps from Duval Street and 9 minutes by foot from Ernest Hemingway Home and ...
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

Key West
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.
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location

Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location

Key West
The price is AU$1,641 per night from 16 Apr to 17 Apr
AU$1,641
includes taxes & fees
16 Apr - 17 Apr
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 ...
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location
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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
1059 Holiday Homes
Lowest Price
AU$427
Highest Price
AU$1,641
Popular accommodation
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!, EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!, Spec.Feb.24-Mar 1 @229+ w. 3 night stay close beach, Feb 3-10 $245 off the rates close beach full kitchen & patio, ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!, Captain's Daughter: Oversized home for the whole family w/private pool & dock, BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!, SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!, Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location

Top trending hotels in Key West

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 AU$542 per night from 21 Apr to 22 Apr
AU$542
includes taxes & fees
21 Apr - 22 Apr
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 8 minutes from Duval ...
Beachside Resort & Residences
Southernmost Beach Resort

Southernmost Beach Resort

4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
The price is AU$895 per night from 7 Apr to 8 Apr
AU$895
includes taxes & fees
7 Apr - 8 Apr
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 ...
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 AU$632 per night from 4 May to 5 May
AU$632
includes taxes & fees
4 May - 5 May
Located in Key West, Margaritaville Beach House Key West is by the ocean, within a 5-minute drive of Smathers Beach and Fort East Martello Museum and ...
Margaritaville Beach House Key West
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Fairfield Inn and Suites by Marriott Key West

Fairfield Inn and Suites by Marriott Key West

3 out of 5
2400 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is AU$427 per night from 4 May to 5 May
AU$427
includes taxes & fees
4 May - 5 May
With a stay at Fairfield Inn and Suites by Marriott Key West, you'll be centrally located in Key West, within a 5-minute drive of Duval Street and Florida Keys ...
Fairfield Inn and Suites by Marriott Key West
Don't see what you're looking for?
See all available properties in Key West
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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.