Upper Matecumbe Key pickleball Stays, Resort Rentals, & Homes
About Upper Matecumbe Key Vacation Rentals
Discover over 1376 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 708.26 ft², with prices averaging US $824 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.
Top Pickleball-Ready Accommodation Types in Upper Matecumbe Key
| Type | Count |
|---|---|
| Vacation Homes | 807 |
| Holiday Apartments | 120 |
| Villas | 97 |
| Cottages | 12 |
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.
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.
Other Places to Stay in Upper Matecumbe Key, FL
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!
- ISLAMORADA, ANGLERS REEF PRISTINE HOME Pool, Dock, Beach, Kayaks, Paddle Boards
- Truly OceanFRONT-PanoramicOceanViews-WraparoundDecks-QuietLocation-AvailableSlip
- Stunning Oceanfront Home located in Islamorada Florida
- ☀️Luxury 3 BR Remodeled! Ocean View PoolSpa, MarinaBikes Boat Slip Tennis/Pickle
- A little Piece of Heaven to wash your worries away
- Next available August 8th, 2026 - Stunning Oceanfront Estate - Private Pool
- Beautiful 'Keysey' Condo in Bay Harbour Gated Community 26-0169
- Peacock Shores Islamorada - Vacation On The Beach!
- Just a Few Friends - Ocean View and Bring your Boat!
- Islamorada Boaters Paradise with 70' Dock and private beach access.
How many pickleball-ready properties have private pools in Upper Matecumbe Key?
Discover 194 accommodations with private or nearby pickleball courts in Upper Matecumbe Key. Some of the best destinations to stay and play pickleball are:
- 5 Star Modern Oceanfront Islamorada Townhome on the Beach!
- Pineapple Beach by Florida Keys Luxury Rentals
- Renovated Anglers Reef 2BR + Sleeper + Ocean Views, Pool, Marina, Sleeps 8
- Beach Dream House, relax and enjoy the clear waters of Islamorada FL
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 1376 properties listed in Upper Matecumbe Key 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 (1)
| Neighborhood | Property Count |
|---|---|
| Coral Cove Vacation Rentals in Florida | 636 |
