87+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Florida
  3. Miami
  4. Westchester

Westchester pickleball Stays, Resort Rentals, & Homes

About Westchester Vacation Rentals

Discover over 87 amazing vacation rental options in Westchester 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 Westchester.

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 1287.1 ft², with prices averaging US $502 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 Westchester.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Westchester

Type Count
Vacation Homes 70
Holiday Apartments 13
Villas 3

Use these Quick Filters to Find a Vacation Rental in Westchester

★ 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 Westchester with PickleTrip™.

Weather in Westchester, FL

View the weather forecast for Westchester before booking your Westchester 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 Westchester, FL

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


Coral Way Shopping Area
Coral Estates Park
Leon Medical Centers - Westchester
PortMiami
Ocean Drive
Hard Rock Stadium
Dolphin Mall
American Airlines Arena
Aventura Mall
Bayside Marketplace
Miami Beach Boardwalk
Collins Avenue Shopping Area
Miami Beach Convention Center
Fontainebleau
Lincoln Road Mall
University of Miami
Bayfront Park
Brickell City Centre
Miami Seaquarium

Other Places to Stay in Westchester, FL


Coral Estates Park 361 Properties
Leon Medical Centers - Westchester 345 Properties
Coral Way Shopping Area 42 Properties
Olympia Heights 27 Properties

Frequently Asked Questions About Westchester?

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

How many pickleball-ready properties have private pools in Westchester?

Discover 9 accommodations with private or nearby pickleball courts in Westchester. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Westchester? 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 Westchester?

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 87 properties listed in Westchester 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 (1) 
Neighborhood Property Count
Coral Terrace Vacation Rentals in Miami, Florida 59

People Also Ask

There are 87 Westchester, FL Vacation Rentals

Recently Booked Vacation Rentals in Westchester