Beginning of main content

Get 24/7 travel help, thanks to our Customer First Guarantee

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Featured Cottages in Key West

Get Rates
Simonton Court Cottages

Simonton Court Cottages

3.5 out of 5.0 910 Simonton, Key West, FL
Free WiFi in public areas and a garden are available at this cottage.
 
Get Rates
Downtown Location in Historic District

Downtown Location in Historic District

Key West, FL
Located in Key West Historic District, this historic cottage is within a 10-minute walk of Duval Street and Key West Butterfly and Nature Conservatory. South Beach and Southernmost Point are also within 15 minutes.
 
Get Rates
New! ~little Truman Cottage~ Modern Cottage w/ Shared Pool In Great Location!

New! ~little Truman Cottage~ Modern Cottage w/ Shared Pool In Great Location!

Key West, FL
Located in Key West Historic District, this historic cottage is steps from Key West Lighthouse and Keeper's Quarters Museum, Duval Street, and Ernest Hemingway Home and Museum. Southernmost Point and South Beach are also within 10 minutes.
 
Get Rates
Downtown Cottage in Historic District

Downtown Cottage in Historic District

Key West, FL
Located in Key West Historic District, this historic cottage is within a 10-minute walk of Duval Street and Key West Butterfly and Nature Conservatory. South Beach and Southernmost Point are also within 15 minutes.
 
Get Rates
Southernmost Santuary

Southernmost Santuary

3.0 out of 5.0 1330 Simonton Street, Key West, FL
An area shuttle is available at this cottage, along with free WiFi in public areas and a terrace. Concierge services are provided for your convenience.
 
Get Rates
Simonton Court Cottages

Simonton Court Cottages

3.5 out of 5.0 910 Simonton Street, Key West, FL
This cottage doesn't skimp on freebies - guests have free WiFi and a free area shuttle. Concierge services are provided for your convenience.
 
Get Rates
Pete's West Cottage Steps From Duval

Pete's West Cottage Steps From Duval

Key West, FL
Located in Key West Historic District, this cottage is steps from Key West Butterfly and Nature Conservatory and Duval Street. South Beach and Ernest Hemingway Home and Museum are also within 10 minutes.
 
Get Rates
Sea Breeze Cottage in Truman Annex Location! Location! Location!

Sea Breeze Cottage in Truman Annex Location! Location! Location!

Key West, FL
A garden is available at this cottage.
 
Get Rates
~ Solaris Garden ~ Enjoy Old Town Livin' Just A Short Walk to All the Action!

~ Solaris Garden ~ Enjoy Old Town Livin' Just A Short Walk to All the Action!

Key West, FL
A garden is available at this cottage.
 
Get Rates
~ Chick-a-pea Cottage ~ Breathtaking Home w/ Pool & Parking, 1 Block to Duval

~ Chick-a-pea Cottage ~ Breathtaking Home w/ Pool & Parking, 1 Block to Duval

Key West, FL
An outdoor tennis court is featured at this cottage, along with a garden.
 
Get Rates
Pete's East Cottage: Cypress East Cottage Steps From Duval

Pete's East Cottage: Cypress East Cottage Steps From Duval

Key West, FL
Located in Key West Historic District, this cottage is steps from Key West Butterfly and Nature Conservatory and Duval Street. South Beach and Ernest Hemingway Home and Museum are also within 10 minutes.
 
Get Rates
Downtown Cottage Just off Famous Duval Street

Downtown Cottage Just off Famous Duval Street

Key West, FL
A garden is available at this cottage.
 
Map

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…

What is vacation high season for Key West?

The busiest months for Key West are .

What is the price range for accommodations in Key West?

We have up to a variety of accommodations available in Key West, ranging from $233 to $424.

How many Cottages options are in Key West?

Book your next Cottages stay through Travelocity today and choose from 794 available options.

When is the offseason for Key West?

Travelers to Key West can find smaller crowds during the months of .

How cheap are Cottages Key West?

Travelers to Key West can find Cottages prices as low as $233.

When is high season in Key West?

Key West welcomes visitors year-round, but are the most popular months.

What is the quality of hotels in and around Key West?

Customers who have stayed in hotels near Key West give them an average rating of 0.0 out of 5.

Top Trending Hotels in Key West

See all 794 Properties in Key West
Southernmost Beach Resort $424
Southernmost Beach Resort

Southernmost Beach Resort

1319 Duval Street, Key West, FL
     
    4.0 out of 5.0 Stars

    Located in Key West Historic District, this beachfront hotel is in the city center and within 1 mi (2 km) of South Beach, Fort Zachary Taylor Historic State Park, and Southernmost Point.

    Ibis Bay Beach Resort $237
    Ibis Bay Beach Resort

    Ibis Bay Beach Resort

    3101 N. Roosevelt Blvd, Key West, FL
       
      2.5 out of 5.0 Stars

      Nestled on the beach, this Key West hotel is within 3 mi (5 km) of Key West Naval Station, Smathers Beach, and South Beach. Duval Street and Southernmost Point are also within 3 mi (5 km).

      24 North Hotel Key West $233
      24 North Hotel Key West

      24 North Hotel Key West

      3820 North Roosevelt Boulevard, Key West, FL
         
        4.0 out of 5.0 Stars

        Located in New Town, this hotel is 2.4 mi (3.9 km) from Key West Harbour and within 6 mi (10 km) of Key West Lighthouse and Keeper's Quarters Museum and Key West Butterfly and Nature Conservatory. Southernmost Point and Mallory Square are also within 6 mi (10 km).

        Oceans Edge Key West Resort, Hotel & Marina $239
        Oceans Edge Key West Resort, Hotel & Marina

        Oceans Edge Key West Resort, Hotel & Marina

        5950 Peninsular Avenue, Key West, FL
           
          4.0 out of 5.0 Stars

          Situated in Key West, this golf hotel is within 1 mi (2 km) of Key West Naval Station and Key West Harbour. Key West Golf Club is 2.1 mi (3.4 km) away.

          Popular Accommodation Searches

          *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.