Florida Keys pickleball Stays, Resort Rentals, & Homes
About Florida Keys Vacation Rentals
Discover over 14196 amazing vacation rental options in Florida Keys 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 Florida Keys.
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 827.72 ft², with prices averaging US $662 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 Florida Keys.
Top Pickleball-Ready Accommodation Types in Florida Keys
| Type | Count |
|---|---|
| Vacation Homes | 8647 |
| Holiday Apartments | 1262 |
| Villas | 366 |
| Cottages | 283 |
Use these Quick Filters to Find a Vacation Rental in Florida Keys
★ 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 Florida Keys with PickleTrip™.
Weather in Florida Keys, FL
View the weather forecast for Florida Keys before booking your Florida Keys Vacation Rentals to confirm your best time to go.
Top Attractions Around Florida Keys, FL
PickleTrip offers a large selection of top attractions around Florida Keys . Research things to do on your vacation before you visit Florida Keys.
Other Places to Stay in Florida Keys, FL
Frequently Asked Questions About Florida Keys?
What are the top vacation rentals, resorts, and hotels in Florida Keys 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 Florida Keys. 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 Florida Keys!
- Oceanfront Key Largo Paradise~Private Beach~Pool~Tennis~Marina~Cafe/Bar
- Summer Fun Awaits! Clean and Cozy w TOP FLOOR VIEWS.Your Home Away From Home!
- Guest Favorite Key Largo | Modern Luxury Coastal Views Beach Pools Quiet Privacy
- ISLAMORADA, ANGLERS REEF PRISTINE HOME Pool, Dock, Beach, Kayaks, Paddle Boards
- Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
- Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
- Florida Keys Paradise Awaits!
- Resort-Style 4BR/4BA Mariner’s Club Key Largo Pools Marina Pickleball
- 3212 Across from Pool * King & Queen/Twin Bunk Bed
- Waterfront! Why rent on a canal when you can be on Bonefish Bay.Newly Remodeled
How many pickleball-ready properties have private pools in Florida Keys?
Discover 2969 accommodations with private or nearby pickleball courts in Florida Keys. Some of the best destinations to stay and play pickleball are:
- Peace of Paradise- Inch Beach membership, private pool, beach views from porch!
- Luxury Seaside Escape ~ Heated Pool w Jacuzzi ~ Elevator ~ Dock ~ Scenic Views
- Parking, Heated Pool, Pet Friendly - Seagate House
- WATERFRONT Home on Deep Canal with private Pool, Spa and Dockage
Which vacation rentals, resorts, or hotels in Florida Keys is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Florida Keys? 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.
- Key Colony Beach Waterfront property with Cabana Club
- Villa Valbuena Ocean Pearl Key Largo Pool Restaurant Marina Pickleball
- Atlantic Paradise by Avantstay Great Location w/Balcony, Outdoor Dining & Shared Pool & Hot Tub!
How many PickleTrip vacation rentals or resorts are available in Florida Keys?
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 14196 properties listed in Florida Keys 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 (16)
| Neighborhood | Property Count |
|---|---|
| Key West Historic District Vacation Rentals in Florida | 2409 |
| Old Town Vacation Rentals in Florida | 2371 |
| Downtown Vacation Rentals in Florida | 992 |
| Uptown - Upper Duval Vacation Rentals in Florida | 761 |
| Historic Seaport Vacation Rentals in Florida | 387 |
| Truman Annex Vacation Rentals in Florida | 349 |
| New Town Vacation Rentals in Florida | 107 |
| Bahama Village Vacation Rentals in Florida | 92 |
| Little Venice Vacation Rentals in Florida | 56 |
| Venetian Shores Vacation Rentals in Florida | 48 |
| Key Largo Village Vacation Rentals in Florida | 34 |
| Indigo Reef Marina Homes Vacation Rentals in Florida | 29 |
| Lower Matecumbe Beach Vacation Rentals in Florida | 26 |
| Pirates Cove Vacation Rentals in Florida | 1351 |
| Coral Lagoon Vacation Rentals in Florida | 1807 |
| Sunset Cove Vacation Rentals in Florida | 1403 |
