Create your free account
Sign in to your account
Find a cheaper way to wander? We'll match it and refund the difference.
Wherever you wander, cancel or rebook most flights within 24 hours without fees.
Need help on your journey? Use our 24/7 social media support @TravelocityHelp.
Featured Cottages in Key West
Downtown Cottage Just off Famous Duval Street
Key WestLocated in Key West Historic District, this historic property is within 6 mi (10 km) of South Beach, Southernmost Point, and Mallory Square. Smathers Beach and Key West Butterfly and Nature Conservatory are also within 6 mi (10 km).
"tides ON Simonton" ~ Perfectly Located Just off Duval and all the Fun!
Key West
Downtown Location in Historic District
Key WestLocated in Key West Historic District, this historic property is within 6 mi (10 km) of South Beach, Southernmost Point, and Mallory Square. Smathers Beach and Key West Butterfly and Nature Conservatory are also within 6 mi (10 km).
Simonton Court Cottages
910 Simonton, Key WestLocated in Key West Historic District, this cottage is 0.1 mi (0.1 km) from Duval Street and within 6 mi (10 km) of South Beach and Southernmost Point. Mallory Square and Smathers Beach are also within 6 mi (10 km).
Downtown Cottage in Historic District
Key WestLocated in Key West Historic District, this historic property is within 6 mi (10 km) of South Beach, Southernmost Point, and Mallory Square. Smathers Beach and Key West Butterfly and Nature Conservatory are also within 6 mi (10 km).
Sea Breeze Cottage in Truman Annex Location! Location! Location!
Key WestThis historic property is located in the heart of Key West, walking distance from Florida Keys Eco - Discovery Center, Duval Street, and Harry S. Truman Little White House. Also nearby are Southernmost Point and Mallory Square.
Tropical Garden Oasis, Walking Distance From to the World Famous "duval Street"
Key WestThis property is located in Key West (Key West Historic District), close to Simonton Beach, South Beach, and Duval Street. Also nearby are Key West Butterfly and Nature Conservatory and Ernest Hemingway Home and Museum.
Eliza's Escape Apartment 4
1320 Eliza Street, Key WestSituated in Key West, this cottage is within 6 mi (10 km) of Higgs Beach, South Beach, and Smathers Beach. Southernmost Point and Mallory Square are also within 6 mi (10 km).
Old Town Key West Cottage
Key WestSituated by the ocean, this property is within 6 mi (10 km) of Southernmost Point, South Beach, and Mallory Square. Smathers Beach and Key West Butterfly and Nature Conservatory are also within 6 mi (10 km).
Completely Renovated, 3 Blks From Duval /private Heated Pool
Key WestLocated in Key West Historic District, this historic property is within 6 mi (10 km) of Key West Butterfly and Nature Conservatory, South Beach, and Southernmost Point. Mallory Square and Smathers Beach are also within 6 mi (10 km).
Southernmost Santuary
1330 Simonton Street, Key WestLocated in Key West Historic District, this cottage is steps from South Beach, Duval Street, and Key West Butterfly and Nature Conservatory. Southernmost Point and Mallory Square are also within 6 mi (10 km).
William's Loft by AT Home IN KEY West
Key WestLocated in Key West Historic District, this property is within 6 mi (10 km) of Nancy Forrester's Secret Garden, South Beach, and Southernmost Point. Mallory Square and Smathers Beach are also within 6 mi (10 km).
Key West Cottages For Rent
Dreaming of a getaway that’s reminiscent of a fairytale? Travelocity doesn’t have magic wands or talking animals in our inventory—at least, none that we can find—but we do have holiday cottages in Key West that will make you feel like you’ve stepped inside your vacation dreams.
The word “cottage” may make you think of whitewashed walls, flower print curtains, and sprawling views of rolling green hills—lucky for you, we do offer tons of country cottages that were furnished with a rustic feel in mind. Appreciate the vase of daffodils on your dining room table, and peek out the window onto the private patio that surrounds yours and other rustic cottages in the area.
These charming “home away from homes” have long been a beacon for those who love the outdoors, so pick a spot peppered with hiking trails and spend lazy afternoons meandering through the gorgeous scenery Key West is known for. Snap some pictures while you’re at it—you’ll want to remember sunset over this waterfall for the rest of your life. When the sun goes down, cuddle up in front of a cheerful fire, or head into town to explore the shops, restaurants, and art galleries that have sprung up over the years. Ah, it’s nice to return to civilization every once in a while, isn’t it?
Whether you select cottages minutes away from the bustling city center, or coastal cottages that are footsteps from the sand and surf, you’ll find the accommodation you’re looking for here on Travelocity. Just because you’re booking a place that reminds you of a fairytale doesn’t mean you need a fairy godmother to find the best deal around! Just a gnome…
More Places To Stay in Key West
Top Trending Hotels in Key West
Havana Cabana at Key West
3420 N. Roosevelt Blvd, Key WestSituated near the airport, this hotel is within 6 mi (10 km) of Fort East Martello Museum and Gallery, Smathers Beach, and South Beach. Southernmost Point and Mallory Square are also within 6 mi (10 km).
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key WestSituated in Key West, this golf hotel is within 6 mi (10 km) of Key West Harbour, Smathers Beach, and South Beach. Southernmost Point and Mallory Square are also within 6 mi (10 km).
24 North Hotel Key West
3820 North Roosevelt Boulevard, Key WestSituated near the airport, this hotel is within 6 mi (10 km) of Key West Harbour, Key West Butterfly and Nature Conservatory, and Southernmost Point. Mallory Square and Fort Zachary Taylor Historic State Park are also within 6 mi (10 km).
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd, Key WestThe white-sand beach of Ibis Bay Beach Resort is a 5-minute drive from downtown Key West. Both the Ernest Hemingway Home & Museum and Southernmost Point are 17 minutes away by bike, and Sunset Pier on Duval Street is a 10-minute cab ride. Key West International Airport is 2.8 miles (4.5 km) away.