Holiday Homes in Key West

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Featured Holiday Homes in Key West

Our top choices for Key West holiday homes

Kingfish Keep | Lively Escape on Duval! Balcony!
Living area

Kingfish Keep | Lively Escape on Duval! Balcony!

10.0 out of 10, Exceptional, (18)
"Awesome location with excellent communication. "
The price is AU$530
includes taxes & fees
26 Aug - 27 Aug
Kingfish Keep | Lively Escape on Duval! Balcony!
Poolside Cottage #411
Outdoor dining

Poolside Cottage #411

9.8 out of 10, Exceptional, (52)
"Lovely home to stay in for a couple of nights on Key West"
The price is AU$478
includes taxes & fees
26 Aug - 27 Aug
Poolside Cottage #411
Poolside Cottage #412
Outdoor dining

Poolside Cottage #412

9.2 out of 10, Wonderful, (25)
"The property and our place was really nice. Would definitely stay again. "
The price is AU$478
includes taxes & fees
26 Aug - 27 Aug
Poolside Cottage #412
Party Like A Local in Key West, 1 bedroom 1 bath yacht at marina.
Interior

Party Like A Local in Key West, 1 bedroom 1 bath yacht at marina.

The price is AU$731
includes taxes & fees
26 Aug - 27 Aug
Party Like A Local in Key West, 1 bedroom 1 bath yacht at marina.
Duval Hideaway | Dog-Friendly Home w/ Shared Hot Tub, Patio & Prime Location
Terrace/patio

Duval Hideaway | Dog-Friendly Home w/ Shared Hot Tub, Patio & Prime Location

9.6 out of 10, Exceptional, (17)
"Perfect location for enjoying Duval Street. "
The price is AU$709
includes taxes & fees
1 Sept - 2 Sept
Duval Hideaway | Dog-Friendly Home w/ Shared Hot Tub, Patio & Prime Location
Charming 1-Bedroom, 1-Beth Sailboat in wonderful Key West
Outdoor pool

Charming 1-Bedroom, 1-Beth Sailboat in wonderful Key West

The price is AU$707
includes taxes & fees
1 Sept - 2 Sept
Charming 1-Bedroom, 1-Beth Sailboat in wonderful Key West
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Property grounds

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

9.8 out of 10, Exceptional, (112)
"Very comfortable house in a great location. "
The price is AU$840
includes taxes & fees
26 Aug - 27 Aug
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Sweet Caroline by Brightwild Pool Parking
House

Sweet Caroline by Brightwild Pool Parking

2.0 star property
The price is AU$1,438
includes taxes & fees
16 Sept - 17 Sept
Sweet Caroline by Brightwild Pool Parking
Docked in Paradise
Terrace/patio

Docked in Paradise

The price is AU$675
includes taxes & fees
31 Aug - 1 Sept
Docked in Paradise
Luxury two floor apartment in prime location of famous Duval Street
Beach towels

Luxury two floor apartment in prime location of famous Duval Street

9.6 out of 10, Exceptional, (82)
"Perfect place to stay. Great location. "
The price is AU$1,125
includes taxes & fees
7 Sept - 8 Sept
Luxury two floor apartment in prime location of famous Duval Street
Pescado Penthouse | Vibrant Retreat Overlooking Duval Street!
3 bedrooms, WiFi

Pescado Penthouse | Vibrant Retreat Overlooking Duval Street!

10.0 out of 10, Exceptional, (6)
"Great location and very nice place."
The price is AU$1,346
includes taxes & fees
1 Sept - 2 Sept
Pescado Penthouse | Vibrant Retreat Overlooking Duval Street!
Yellowfin Ledge | Inviting Getaway On Duval! Balcony!
1 bedroom, WiFi, bed sheets

Yellowfin Ledge | Inviting Getaway On Duval! Balcony!

9.4 out of 10, Exceptional, (20)
"Little condo across from Cuban coffee queen. A little bit of a distance from main bars and shopping, but still nice for what it’s needed for. "
The price is AU$439
includes taxes & fees
26 Aug - 27 Aug
Yellowfin Ledge | Inviting Getaway On Duval! Balcony!
Wahoo Way | Charming Hideaway On Duval Street!
1 bedroom, free WiFi, bed sheets

Wahoo Way | Charming Hideaway On Duval Street!

9.0 out of 10, Wonderful, (16)
"Small place, but clean and everything needed for 2 people to stay I "
The price is AU$408
includes taxes & fees
26 Aug - 27 Aug
Wahoo Way | Charming Hideaway On Duval Street!
Harbor Walk Hideaways | Group Compound In Old Town!
Outdoor dining

Harbor Walk Hideaways | Group Compound In Old Town!

9.8 out of 10, Exceptional, (6)
"I come to Key West often. This is the best location and property I’ve stayed in. Everything was wonderful. I will book this every single time I come. it is perfect for big families, couples or a group of friends. "
The price is AU$1,431
includes taxes & fees
1 Sept - 2 Sept
Harbor Walk Hideaways | Group Compound In Old Town!
Capmar House by Brightwild Huge Home Pool
House

Capmar House by Brightwild Huge Home Pool

2.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
The price is AU$3,024
includes taxes & fees
7 Sept - 8 Sept
Capmar House by Brightwild Huge Home Pool
Waterfront Luxury Home - Tidelands House
House

Waterfront Luxury Home - Tidelands House

2.0 star property
The price is AU$5,138
includes taxes & fees
7 Sept - 8 Sept
Waterfront Luxury Home - Tidelands House
Atlantis House Suites
Outdoor dining

Atlantis House Suites

2.0 star property
10.0 out of 10, Exceptional, (1)
Atlantis House Suites
Palmgale House in Key West
House

Palmgale House in Key West

2.0 star property
The price is AU$4,070
includes taxes & fees
7 Sept - 8 Sept
Palmgale House in Key West
Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location
Fridge, microwave, coffee/tea maker, toaster

Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location

9.0 out of 10, Wonderful, (180)
"Comfortable no frills 3 bedroom home. Close to great bars and restaurants. Would recommend for the location "
The price is AU$837
includes taxes & fees
26 Aug - 27 Aug
Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location
Waterlane House by Brightwild Pool Boat Dock
House

Waterlane House by Brightwild Pool Boat Dock

2.0 star property
The price is AU$2,975
includes taxes & fees
23 Sept - 24 Sept
Waterlane House by Brightwild Pool Boat Dock
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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Top Key West Hotel Reviews

Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"The property was excellent, located in the heart of everything!! 😍"
Bonita 4-night trip
Posted 1 day ago
Beachside Resort & Residences