1338+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Florida
  3. Upper Matecumbe Key

Upper Matecumbe Key pickleball Stays, Resort Rentals, & Homes

About Upper Matecumbe Key Vacation Rentals

Discover over 1338 amazing vacation rental options in Upper Matecumbe Key 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 Upper Matecumbe Key.

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 767.86 ft², with prices averaging US $774 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 Upper Matecumbe Key.

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Top Pickleball-Ready Accommodation Types in Upper Matecumbe Key

Type Count
Vacation Homes 784
Holiday Apartments 116
Villas 113
Cottages 10

Use these Quick Filters to Find a Vacation Rental in Upper Matecumbe Key

★ 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 Upper Matecumbe Key with PickleTrip™.

Weather in Upper Matecumbe Key, FL

View the weather forecast for Upper Matecumbe Key before booking your Upper Matecumbe Key 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 Upper Matecumbe Key, FL

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


Bud n' Mary's Dive Center
Hurricane Monument
History of Diving Museum
Matecumbe United Methodist Church
Florida Keys Brewing Co.
John Pennekamp Coral Reef State Park
Jimmy Johnson's Big Chill
Theater of the Sea
Dolphins Plus Bayside
Dolphin Cove
Founders Park
Anne's Beach
Caribbean Club Bar
Dolphins Plus
Harry Harris Park
Bluefin Rock Harbor Marina
Florida Keys Dive Center
Harry Harris Park
Florida Keys Flats Fishing
Islamorada County Park

Other Places to Stay in Upper Matecumbe Key, FL


Islamorada 938 Properties
History of Diving Museum 811 Properties
Matecumbe United Methodist Church 647 Properties
Florida Keys Brewing Co. 632 Properties
Hurricane Monument 630 Properties
Coral Cove 542 Properties
Bud n' Mary's Dive Center 522 Properties

Frequently Asked Questions About Upper Matecumbe Key?

What are the top vacation rentals, resorts, and hotels in Upper Matecumbe Key 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 Upper Matecumbe Key. 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 Upper Matecumbe Key!

How many pickleball-ready properties have private pools in Upper Matecumbe Key?

Discover 186 accommodations with private or nearby pickleball courts in Upper Matecumbe Key. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Upper Matecumbe Key? 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 Upper Matecumbe Key?

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 1338 properties listed in Upper Matecumbe Key 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 Cove Vacation Rentals in Florida 542

People Also Ask

There are 1338 Upper Matecumbe Key, FL Vacation Rentals

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