4582+ Private Villas and Holiday Rentals in Key West |
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Key West Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Key West

Discover more than 4582 vacation rentals available in Key West. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Key West.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Key West, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Key West. On average, places to stay near Key West offer 767.92 ft², with nightly prices averaging US $705.

With Casai, finding and comparing holiday rentals in Key West is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Things to Know Before You Visit Key West

Getting to Key West is easy. From Miami, you simply hop on Highway 1 and take it all the way to the southern most point in the U.S., the iconic Key West buoy. The drive will be about four hours long but could take much longer if you make stops along the way to the incredible island towns throughout the Florida Keys. If you are flying in, the Key West International Airport is small but efficient and well-suited for travel to this island city.

Key West is known as a great spot for those who love the outdoors, and there are plenty of things to do that will appeal to this type of traveler. Rent a boat and go diving with fish. Snorkel along the many reefs in the area where youll find tropical fish as well as unique coral species. Exploring by boat can also give you an opportunity to see rare birds and mangrove islets, as well as the sites used by the Conch Republic in their famous protest against the government.

If youd rather spend your time shopping, dining, and enjoying the local bar scene, you wont be disappointed in Key West. A stroll down Duval Street in the historic downtown will give you a plethora of food and entertainment options to choose from.

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Top Accommodation Types in Key West

Type Count
Vacation Homes 2524
Holiday Apartments 559
Cottages 109
Villas 41

Use these Quick Filters to Find a Holiday Rental in Key West

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Key West.

Weather in Key West, FL

View the weather forecast for Key West before booking your Key West Vacation Rentals to confirm your best time to go.

December - February
High 81°F       Low 67°F
March - May
High 87°F       Low 70°F
June - August
High 91°F       Low 80°F
September - November
High 90°F       Low 73°F

Top Attractions Around Key West, FL

Casai offers a large selection of top attractions around Key West . Research things to do on your vacation before you visit Key West.


Duval Street
Smathers Beach
Southernmost Point
Mallory Square
Dry Tortugas National Park
South Beach
Higgs Beach
Key West Harbour
Key West Aquarium
Ernest Hemingway Home and Museum
Fort Zachary Taylor Historic State Park
Key West Butterfly and Nature Conservatory
Saddlebunch Keys
Harry S. Truman Little White House
Key West Shipwreck Museum
Key West Golf Club
Key West Lighthouse and Keeper's Quarters Museum
Ripley's Believe It or Not
Audubon House and Tropical Gardens

Other Places to Stay in Key West, FL


Key West Historic District 2,465 Properties
Old Town 2,402 Properties
Duval Street 1,802 Properties
Downtown 1,038 Properties
Uptown - Upper Duval 764 Properties
Historic Seaport 406 Properties
Truman Annex 343 Properties
New Town 115 Properties
Bahama Village 93 Properties
The Meadows 86 Properties
Meadows 86 Properties
Midtown 51 Properties

Frequently Asked Questions About Key West?

What are the top holiday rentals in Key West?

With numerous options available in Key West, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Key West:

How many holiday rentals have private pools in Key West?

Discover a selection of holiday rentals with private pools near Key West with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Key West are best for families?

If you're searching for a family-friendly holiday home in Key West, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Key West:

How many Casai.nz holiday rentals are available in Key West?

As of 2025, Casai boasts over 4582 properties listed in the Key West area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Key West.

Nearby Neighborhood (15) 
Neighborhood Property Count
Key West Historic District Vacation Rentals in Key West, Florida 2465
Old Town Vacation Rentals in Key West, Florida 2402
Downtown Vacation Rentals in Key West, Florida 1038
Uptown - Upper Duval Vacation Rentals in Key West, Florida 764
Historic Seaport Vacation Rentals in Key West, Florida 406
Truman Annex Vacation Rentals in Key West, Florida 343
New Town Vacation Rentals in Key West, Florida 115
Bahama Village Vacation Rentals in Key West, Florida 93
Meadows Vacation Rentals in Key West, Florida 86
The Meadows Vacation Rentals in Key West, Florida 86
Midtown Vacation Rentals in Key West, Florida 51
White St. Gallery Vacation Rentals in Key West, Florida 25
White Street Gallery District Vacation Rentals in Key West, Florida 25
Sunset Key Vacation Rentals in Key West, Florida 3214
Geiger Key Vacation Rentals in Key West, Florida 35

People Also Ask

There are 4582 Key West, FL Holiday Rentals

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