158+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Florida
  3. Miami
  4. Cutler Bay

Cutler Bay pickleball Stays, Resort Rentals, & Homes

About Cutler Bay Vacation Rentals

Discover over 158 amazing vacation rental options in Cutler Bay 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 Cutler Bay.

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 969.72 ft², with prices averaging $389 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 Cutler Bay.

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Top Pickleball-Ready Accommodation Types in Cutler Bay

Type Count
Vacation Homes 115
Holiday Apartments 17
Villas 17

Use these Quick Filters to Find a Vacation Rental in Cutler Bay

★ 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 Cutler Bay with PickleTrip™.

Weather in Cutler Bay, FL

View the weather forecast for Cutler Bay before booking your Cutler Bay 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 Cutler Bay, FL

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


PortMiami
Ocean Drive
Dolphin Mall
American Airlines Arena
Bayside Marketplace
Miami Beach Boardwalk
Collins Avenue Shopping Area
Miami Beach Convention Center
Lincoln Road Mall
University of Miami
Bayfront Park
Brickell City Centre
Miami Seaquarium
Dadeland Mall
Vizcaya Museum and Gardens
Jungle Island
Miami Beach Marina
Florida International University
James L. Knight Center

Other Places to Stay in Cutler Bay, FL


Lakes by the Bay 132 Properties

Frequently Asked Questions About Cutler Bay?

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

How many pickleball-ready properties have private pools in Cutler Bay?

Discover 20 accommodations with private or nearby pickleball courts in Cutler Bay. Some of the best destinations to stay and play pickleball are:

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

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

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 158 properties listed in Cutler Bay 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.


People Also Ask

There are 158 Cutler Bay, FL Vacation Rentals

Recently Booked Vacation Rentals in Cutler Bay