100+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Florida
  3. Fort Myers
  4. Cypress Lake

Cypress Lake pickleball Stays, Resort Rentals, & Homes

About Cypress Lake Vacation Rentals

Discover over 100 amazing vacation rental options in Cypress Lake 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 Cypress Lake.

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 1002.7 ft², with prices averaging US $211 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 Cypress Lake.

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Top Pickleball-Ready Accommodation Types in Cypress Lake

Type Count
Vacation Homes 48
Holiday Apartments 6
Villas 5

Use these Quick Filters to Find a Vacation Rental in Cypress Lake

★ 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 Cypress Lake with PickleTrip™.

Weather in Cypress Lake, FL

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

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Cypress Lake, FL

PickleTrip offers a large selection of top attractions around Cypress Lake . Research things to do on your vacation before you visit Cypress Lake.


Florida Southwestern State College
Barbara B Mann Hall
Cypress Lake Country Club
Golfview Golf and Racquet Club
Barefoot Beach
JetBlue Park at Fenway South
Florida Gulf Coast University
Vanderbilt Beach
Bonita Springs Public Beach
Captiva Beach
Coconut Point Mall
Sanibel Island Southern Beach
Times Square
Hertz Arena
Fishing Pier Fort Myers Beach
Bowman's Beach
Gulf Coast Town Center
Edison and Ford Winter Estates
Manatee Park
Sanibel Island Lighthouse

Other Places to Stay in Cypress Lake, FL


Sandalwood Estates 1,117 Properties
Cypress Lake Country Club 743 Properties
Golfview Golf and Racquet Club 707 Properties
Lakewood Village 685 Properties
Florida Southwestern State College 523 Properties
Barbara B Mann Hall 512 Properties
Cypress Lakes Estates 70 Properties

Frequently Asked Questions About Cypress Lake?

What are the top vacation rentals, resorts, and hotels in Cypress Lake 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 Cypress Lake. 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 Cypress Lake!

How many pickleball-ready properties have private pools in Cypress Lake?

Discover 7 accommodations with private or nearby pickleball courts in Cypress Lake. Some of the best destinations to stay and play pickleball are:

Which vacation rentals, resorts, or hotels in Cypress Lake is best for families looking for a pickleball-getaway?

Looking for a fun and active getaway with pickleball courts in Cypress Lake? 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.

How many PickleTrip vacation rentals or resorts are available in Cypress Lake?

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 100 properties listed in Cypress Lake 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.

Nearby Neighborhood (5) 
Neighborhood Property Count
Cypress Lakes Estates Vacation Rentals in Fort Myers, Florida 70
Town and River Vacation Rentals in Fort Myers, Florida 2141
Sandalwood Estates Vacation Rentals in Fort Myers, Florida 1117
Lakewood Village Vacation Rentals in Fort Myers, Florida 685
Reflection Lakes Vacation Rentals in Fort Myers, Florida 574

People Also Ask

There are 100 Cypress Lake, FL Vacation Rentals

Recently Booked Vacation Rentals in Cypress Lake