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Cottage rentals in Key West

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Top-rated cottage rentals in Key West

Guests agree: these cottages are highly rated for location, cleanliness and more.

Superhost
Cottage in Key West
Old Town home a short walk to Duval/Couples Oasis
Add this listing to your wishlist by clicking the ♥ in the upper right hand corner. This 1 bedroom/1.5 bathroom Key West cottage is the perfect place to relax and enjoy island living. With only 4 blocks to Duval, walking to dinner or to famous sites is easy. Central to Mallory Square and the Southernmost Pointe means that you have your pick of places to choose from. Enjoy the front and back porches as you cool off in the shade. Stylish, clean, and private, you don't want to pass on this retreat.
Superhost
Cottage in Key West
Location, Location, Location! Cute and Convenient!
Charming 2 bedroom house in a 19th century Conch house! in the heart of the Old Town Seaport. Unique property comprising 2 units connected by a doorway.Relax on the private porch or deck.Convenient to all of Old Town.Walk anywhere. One block to the Historic Seaport with ocean front bars/restaurants, sunset cruises, fishing charters and Dante’s pool bar. 4 blocks to Duval Street. Quiet neighborhood coffee shops, bakeries, restaurants, Dive Shops, organic markets. HS internet. 28 night min stay.
Cottage in Key West
Great Old Town Key West Cottage
"La Casita"- Completely remodeled and Fully Furnished Old Town Key West cottage 10 min Walking distance from the White street Pier. Perfect for relaxing or guests who want enjoy Key West and work remotely. Cottage offers everything you'll need for the perfect getaway. TV,s, Internet, desk, Washer and Dryer, SS Appliances , Memory Foam mattress ,outdoor grill and Nespresso coffee maker.28 days minimum stay!

Cottage rentals with a hot tub

Superhost
Cottage in Key West
Darling of Duval @ Old Town - Adorable Cottage
Professional Host
Cottage in Key West
Sunshine Siesta Cottage~Old Town, Pool, Hot Tub
Superhost
Cottage in Key West
The Sunshine House, Best Location in Key West!
Superhost
Cottage in Cudjoe Key
ATLANTIS...Ocean Front Cottage Retreat!
Individual Host
Superhost
Cottage in Cudjoe Key
King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
Individual Host
Superhost
Cottage in Cudjoe Key
Turtle Cove Views @ Venture Out - Waterfront
Professional Host
Superhost
Cottage in Cudjoe Key
NAUTILUS...ocean front cottage retreat ~
Individual Host
Cottage in Cudjoe Key
VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck
Individual Host
Cottage in Key Colony Beach
New listing 2BR Waterview Dog Friendly | Pool
Professional Host
Cottage in Cudjoe Key
Calypso Cottage
Individual Host
Cottage in Cudjoe Key
Walk to the Pool - Venture Out Unit 333
Superhost
Cottage in Cudjoe Key
OCEANIA... water front cottage retreat ~
Individual Host

Pet-friendly cottage rentals

Superhost
Cottage in Key West
Oasis in old town Key West - private heated pool!
Individual Host
Cottage in Key West
1BR | Dog Friendly | Deck | Grill | AC
Professional Host
Cottage in Key West
Tranquil 2BR Dog Friendly | Pool | Patio
Professional Host
Cottage in Big Pine Key
CASA COCO by the CANAL!
Cottage in Key West
A Touch of Bermuda in Key West
Individual Host
Superhost
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
Professional Host
Cottage in Marathon
Tropical Cottages - Cottage # 10
Professional Host
Superhost
Cottage in Marathon
Catch n' Relax Canalfront Cottage in Marathon
Cottage in Marathon
Tropical Cottages - Cottage # 8
Professional Host
Superhost
Cottage in Key West
Garden of Eden Cottage
Professional Host
Cottage in Key West
Charming Old Town Bungalow
Individual Host
Cottage in Key West
Eleanor's Place in Old Town Key West - Dogs Ok
Individual Host

Private cottage rentals

Superhost
Cottage in Key West
Old Town Cottage House in Old Town Key West!
Professional Host
Superhost
Cottage in Key West
Bali Hideaway: A studio cottage that's perfect
Professional Host
Superhost
Cottage in Key West
Island home/Great location/Open for Fantasy Fest!
Superhost
Cottage in Key West
Ann Street Cottage
Professional Host
Superhost
Cottage in Key West
Pete's West Cottage steps from Duval
Professional Host
Superhost
Cottage in Key West
Colony Calypso - A quaint 1 Bedroom Cottage
Professional Host
Superhost
Cottage in Key West
Colony Poolside: A charming bungalow near Duval
Professional Host
Superhost
Cottage in Key West
Pete's East Cottage: Cypress east cottage steps
Professional Host
Superhost
Cottage in Marathon
WATER FRONT COTTAGE W/ MOTHER IN LAW TREETOP SUITE
Cottage in Key West
Colorful 1BR | Pool | Patio | Garage Parking
Professional Host
Cottage in Key West
Casa mango on south street
Professional Host
Superhost
Cottage in Key West
Ann Street Tranquility
Professional Host