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Vacation rentals in Key West

See all Vacation Rentals in Key West
$245
Kimpton Ella's Cottages

Kimpton Ella's Cottages

3.5 out of 5.0 811 Simonton Street, Key West, FL
A marina and an outdoor pool are featured at this cottage. WiFi in public areas is free. Self parking, a terrace, and a garden are also offered.
$329
Hyatt Residence Club Key West, Sunset Harbor

Hyatt Residence Club Key West, Sunset Harbor

3.5 out of 5.0 200 Sunset Lane, Key West, FL
An outdoor pool, self parking, and concierge services are featured at this condo. WiFi in public areas is free.
Coconut Mallory Resort And Marina By Kees Vacations

Coconut Mallory Resort And Marina By Kees Vacations

3.0 out of 5.0 1445 S Roosevelt Blvd, Key West, FL
3.8/5
(38 Reviews)
This condo's 2 outdoor pools and spa tub are among the featured amenities. Guests will appreciate free perks like free self parking and WiFi in public areas. Concierge services and barbecue grills are also provided.
$132
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.
$125
Banana's Foster Guesthouse

Banana's Foster Guesthouse

3.5 out of 5.0 537 Caroline St, Key West, FL
Free WiFi in public areas is available at this apartment.
$202
Dog-friendly Sunrise Suites Condo w/ Shared Pool, hot tub & Free Parking

Dog-friendly Sunrise Suites Condo w/ Shared Pool, hot tub & Free Parking

Key West, FL
This condo features an outdoor tennis court and a spa tub.
PRICES HAVE NEVER BEEN LOWER!

PRICES HAVE NEVER BEEN LOWER!

Key West, FL
Located in Key West Historic District, this historic vacation home is within a 15-minute walk of Duval Street, Higgs Beach, and South Beach. Southernmost Point and Key West Butterfly and Nature Conservatory are also within 1 mi (2 km).
$174
2b/2b Condo Sleeps 6

2b/2b Condo Sleeps 6

Key West, FL
This condo features an outdoor tennis court and a spa tub.
Hidden Beach - the Perfect Place to Stay in Key West

Hidden Beach - the Perfect Place to Stay in Key West

Key West, FL
Nestled on the beach, this Old Town condo building is just steps from Simonton Beach and Duval Street. South Beach and Higgs Beach are also within 10 minutes.
Top Floor Ocean Views From Every Window Newly Renovated for 2020

Top Floor Ocean Views From Every Window Newly Renovated for 2020

Key West, FL
This condo features an outdoor pool and an outdoor tennis court. A fitness center, a spa tub, and a sauna are also on offer.
Brand New! Waterfront 4 Bedroom Condo at Bayfront Suites & Marina

Brand New! Waterfront 4 Bedroom Condo at Bayfront Suites & Marina

Key West, FL
This condo features an outdoor tennis court and a rooftop terrace. Barbecue grills are provided for your convenience.
Luxury Waterfront Home With Private Heated Pool and Lush Landscaping!

Luxury Waterfront Home With Private Heated Pool and Lush Landscaping!

Key West, FL
A spa tub is featured at this vacation home, along with barbecue grills.
Colors OF THE Keys @ THE Foundry Villa Near Duval & Beach + Last KEY Service

Colors OF THE Keys @ THE Foundry Villa Near Duval & Beach + Last KEY Service

Key West, FL
A garden is available at this vacation home.
$230
Beautiful Boat With Wonderful Deck Anchored off of Fleming Key in Key West

Beautiful Boat With Wonderful Deck Anchored off of Fleming Key in Key West

Key West, FL
Situated in Key West, this houseboat is within 1 mi (2 km) of Schooner Western Union, Duval Street, and Mallory Square. Key West Shipwreck Museum and Harry S. Truman Little White House are also within 1 mi (2 km).
Quiet, Quaint, and Conveniently Located! New POOL!

Quiet, Quaint, and Conveniently Located! New POOL!

Key West, FL
Located in Old Town, this historic apartment building is within a 5-minute walk of Duval Street, Southernmost Point, and Ernest Hemingway Home and Museum. South Beach and Key West Butterfly and Nature Conservatory are also within 10 minutes.
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The Best Way to Find your Vacation Rentals in Key West

How cheap can a vacation rental in Key West be?

You can find vacation rentals in Key West for as low as $125 per night.

How do you look for the best vacation rental deals in Key West with Travelocity?

Travelocity provides the best vacation rental deals in various locations throughout Key West so you can create the perfect plan for you. You can search and filter by type of property, amenities, neighborhood, price range, number of bedrooms, and more.

Are cancellations free on vacation rentals with Travelocity?

Each vacation rental has its own cancellation policy. It’s essential to understand the terms of your agreement before booking. Most rentals in Key West can be canceled for free when notifying the property before the cancellation deadline.

What types of vacation rentals are available in Key West?

Short term rentals come in all shapes and sizes. Choose from properties for a wide range of budgets and types of holidays. Families, couples, outdoor adventurers, and leisure travelers alike will find the perfect place for them. Check out our Key West vacation apartments to get started building your trip.

What are the benefits of booking a short-term rental in Key West?

Whether it’s for a summer getaway, a winter excursion, or a routine business trip, Key West vacation homes are often an excellent choice. You can enjoy group vacations with short term rentals to fit your party size. You might take a romantic weekend for two or plan a family reunion, and all stay under one roof. The options are endless, and you can find them on Travelocity.

Why is Travelocity the best site to find your vacation rental in Key West?

With Travelocity, all your travel needs are taken care of in one convenient platform. We offer fantastic deals on our large selection of vacation rentals to get you the most savings and rewards back on every booking. Save more when you bundle bookings together, including car rentals, flights, and activities. Here, you can build custom Key West vacations.

How to cancel your vacation rental with Travelocity?

To cancel your vacation rental, contact the property manager. You can find their contact information in the ‘Itinerary’ section of your Travelocity account. Most properties receive a full refund when you cancel before the cancellation deadline. Policies vary by property, so it’s important to understand the terms before booking. For more information, visit our customer service portal.


*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.