Holiday Rentals in Key West
Revenue impacts this sort order. Learn more
Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 km
114 rentals in Key West.
Ocean Vista
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Sunrise at Seaside Condo 2 Bedroom
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Island Suite @ KW Vacation
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Key West Suites Hotel 205
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Sunrise Suite Key West 2 Bed Rooms 2 Full Baths
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Eleanor's Place in Key West Old Town - Dogs Ok
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
OLD TOWN, 2 Bedrm, Pool, Fully Equipped Kitchen, Wrap around private porch, W/D
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Clean Apartment in Old Town Key West (Best Downtown Locations)
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Clean Apartment in Old Town Key West (Best Downtown Locations)
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Sunshine suit (2/2 apartment)
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
One-bedroom time share suite in the heart of Old Key West
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Key West Suites Hotel unit 201
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Sweet Caroline Seaport Floor 2
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Conch Haven Old Town 1/1 MONTHLY Rental
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Shipyard-1/2 Block Duval Street
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
The Tree House Old Town 2 Bedroom MONTHLY Rental
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
A Change in Latitudes - TRUMAN ANNEX
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Truman Annex-Steps to Famous Duval Street
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Key West, Private Beach, Fishing Pier, Old Town, Galleon Resort
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Cozy Key West Hideaway with a Pool, Digital Workspace, and Privacy
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
'Little Paradise' Historic Seaport Old Town Key West
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Comfy Family Home in a Gorgeous Gated Community
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Tropical Old Town Bungalow: Charming 2nd Floor Unit, Private Spa/Shared Pool, Ne
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterp
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Ella Varela: Gorgeous Conch Cottage in Key West's Heart, Close to Old Town & Bea
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!! SLEEPS 2-4, 3 BLKS TO BEACH
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Lovely 2 bedroom, 2 bath condo at La Brisa.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Nature's Boutique
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Ambrosia - OLD TOWN/HISTORIC SEAPORT, large POOL, wrap around porch, washer/dry
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Southernmost Beauty
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Galleon Key West for New Year's Week
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Casa Del Sol, a Key West Vacation (Truman Annex)
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Key West Gulf front Home with private dock and pool.
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Casa Sol: Discover This Charming, Pet-Friendly Key West Conch House in the Heart
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Salt Ponds Sanctuary: Your Tranquil Escape, Shared Pool/Hot Tub & Proximity to t
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Margaritaville: Live Like a Local in Old Town Key West! Dog-Friendly Conch House
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
NEW LISTING! 40’ Luxury Catamaran Yacht!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Key West Bayfront Paradise - House and Private Pool! Steps from shops and food
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Living On the Hook in Key West Harbour
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Studio Blue
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Lotus Blossom: Discover Paradise, 3BR Home W/ Tropical Courtyard, Hot Tub & Minu
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Single Family Home, 3 Bedroom, 2 Baths, and Pool. Great Value!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Henry's Piece Of Paradise On The Ocean In Key West
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Artist Cottage in Truman Annex
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Ohana Paradise At Historic Seaport ,Old Town, Key West. Private Home.
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
HISTORIC KEY WEST - Cigar House - Sleeps 4
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
New Listing Family Friendly
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Showing results 1-50 of 114