Key West pickleball Stays, Resort Rentals, & Homes
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Luxury Places to Stay in Key West
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Pet-Friendly Villas in Key West
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Key West Villas, Airbnb and Holiday Homes Under $200
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Instantly Bookable Villa Rentals in Key West
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Book a Last Minute Place to Stay in Key West
About Key West Vacation Rentals
Discover over 25 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 390.14 ft², with prices averaging US $295 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.
Top Pickleball-Ready Accommodation Types in Key West
| Type | Count |
|---|---|
| Vacation Homes | 12 |
| Holiday Apartments | 2 |
Use these Quick Filters to Find a Vacation Rental in Key West
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★ 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, IA
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, IA
PickleTrip offers a large selection of top attractions around Key West . Research things to do on your vacation before you visit Key West.
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!
- Eat, Shop, Stroll & More! Stay at this Cozy Bungalow in Dubuque!
- Cozy Log Cabin with Hot Tub & Only 5 Miles from Downtown!
- 3bed 2bath nestled in cozy Grandview neighborhood (pet friendly!)
- Custom Floating Cabin on Mississippi River backwater with a HOT TUB!
- Retro floating cabin on river backwaters. HOT TUB!
- Annabel Lee Barn ~ A Getaway of Warmth & Charm!
- Floating Studio Cabin. HOT TUB!
- 1970s Modern Floating River Cabin-HOT TUB!
- Between Sundown & Chestnut Ski Resorts & 30 min from the Field of Dreams.
- Private king suite DBQ
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 25 properties listed in Key West in 2025, 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.
