Key West pickleball Stays, Resort Rentals, & Homes
About Key West Vacation Rentals
Discover over 5024 amazing vacation rental options in Key West with pickleball courts or nearby facilities. From resorts to hotels, villas to condos, PickleTrip connects you with a vast selection of pickleball-ready amenities at great prices, providing you with the perfect spot to base your next pickleball vacation. Stay and Play pickleball When You Travel and uncover great stays in Key West.
Find exclusive last-minute deals on vacation rentals, resorts, and hotels with private courts and nearby facilities with PickleTrip™, whether you're traveling solo or with a group. Our platform offers a variety of stay options, from vacation rentals to Airbnb-style properties, all with private pickleball courts or nearby facilities. Compare options from multiple suppliers with a single click to find the perfect stay that fits your budget and style. Places to stay near pickleball courts are an average of 764.23 ft², with prices averaging US $827 per night.
With PickleTrip™, you can easily search for and book your next pickleball vacation rental with courts or nearby facilities. Our platform connects you with the ideal holiday rental to create a lifetime of travel memories. Prices listed are often discounted versus rack rates, so you can secure your perfect place to stay today and get ready to play pickleball in Key West.
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.
Top Pickleball-Ready Accommodation Types in Key West
| Type | Count |
|---|---|
| Vacation Homes | 2521 |
| Holiday Apartments | 595 |
| Cottages | 118 |
| Villas | 45 |
Use these Quick Filters to Find a Vacation Rental in Key West
★ Pro Tip: PickleTrip™ is a travel platform, connecting avid pickleball players and enthusiasts with a variety of vacation rentals, resorts, and hotels featuring private pickleball courts or nearby facilities. We curate a vast selection of properties from trusted sources, providing you with unbeatable options and pricing to find the perfect pickleball getaway. Experience unforgettable pickleball matches in Key West with PickleTrip™.
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.
Top Attractions Around Key West, FL
PickleTrip offers a large selection of top attractions around Key West . Research things to do on your vacation before you visit Key West.
Other Places to Stay in Key West, FL
Frequently Asked Questions About Key West?
What are the top vacation rentals, resorts, and hotels in Key West with Courts?
Experience the ultimate pickleball vacation with PickleTrip™. We offer a variety of premium rental properties, resorts, and hotels with private pickleball courts or nearby facilities in Key West. Whether you're a beginner or a seasoned player, we have the perfect destination for you to stay and play. Book now and discover the best pickleball vacation spots in Key West!
- Sunrise Condo at Seaside - KEY WEST!
- 3 bedroom with living room and sitting room and a pool just 2 blocks from Higgs beach
- Your own Private Resort! 50ft Dock on Canal w/Pool, Tiki and RV Hookup!
- 4-bedroom resort style home in awesome Key West with large pool and private deck
- Zen Villa - A Luxurious 3-bedroom Sanctuary with WiFi & a Pool in Old Key West
- *INFINITE HORIZONS @ BIG COPPITT* Waterfront Home & Pool + LAST KEY SERVICES…
- BANYAN ROSE ~ Renovated 4 Bedroom, 2 Bathroom Midtown Home w/Pool!
- ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/Pool, Fitness Area & Beach!
- ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking
- A Duval Street Oasis with balcony overlooking Duval
How many pickleball-ready properties have private pools in Key West?
Discover 863 accommodations with private or nearby pickleball courts in Key West. Some of the best destinations to stay and play pickleball are:
- New Property - Belle of Key West! Old Town 29 nt min.
- Key West Harbor Inn - Adults Only
- Parking, Heated Pool, Pet Friendly - Seagate House
- Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath
Which vacation rentals, resorts, or hotels in Key West is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Key West? With PickleTrip™, you'll have access to a wide selection of top-rated properties that offer private pickleball courts or nearby facilities. Make the most of you getaway and ace your A-game while you travel.
- New Property - Belle of Key West! Old Town 29 nt min.
- Somewhere on the beach
- Atlantic Paradise by Avantstay Great Location w/Balcony, Outdoor Dining & Shared Pool & Hot Tub!
How many PickleTrip vacation rentals or resorts are available in Key West?
PickleTrip™ offers a diverse selection of properties with private pickleball courts or nearby facilities to enhance your pickleball experience on your next trip. With a combination of established great stays and new options in top locations, PickleTrip™ has over 5024 properties listed in Key West in 2026, and the number only continues to grow. By consolidating listings from various providers, PickleTrip™ brings you the best luxury stays for a sporty, professional, and fun travel experience.
Nearby Neighborhood (15)
| Neighborhood | Property Count |
|---|---|
| Key West Historic District Vacation Rentals in Key West, Florida | 2226 |
| Old Town Vacation Rentals in Key West, Florida | 2189 |
| Downtown Vacation Rentals in Key West, Florida | 921 |
| Uptown - Upper Duval Vacation Rentals in Key West, Florida | 711 |
| Historic Seaport Vacation Rentals in Key West, Florida | 366 |
| Truman Annex Vacation Rentals in Key West, Florida | 305 |
| Meadows Vacation Rentals in Key West, Florida | 104 |
| The Meadows Vacation Rentals in Key West, Florida | 104 |
| New Town Vacation Rentals in Key West, Florida | 98 |
| Bahama Village Vacation Rentals in Key West, Florida | 78 |
| Midtown Vacation Rentals in Key West, Florida | 46 |
| White St. Gallery Vacation Rentals in Key West, Florida | 4450 |
| White Street Gallery District Vacation Rentals in Key West, Florida | 4446 |
| Sunset Key Vacation Rentals in Key West, Florida | 3712 |
| Geiger Key Vacation Rentals in Key West, Florida | 51 |
