1522+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Florida
  3. Islamorada

Islamorada pickleball Stays, Resort Rentals, & Homes

About Islamorada Vacation Rentals

Discover over 1522 amazing vacation rental options in Islamorada 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 Islamorada.

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 770.89 ft², with prices averaging US $803 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 Islamorada.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Islamorada

Type Count
Vacation Homes 924
Holiday Apartments 123
Villas 103
Cottages 13

Use these Quick Filters to Find a Vacation Rental in Islamorada

★ 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 Islamorada with PickleTrip™.

Weather in Islamorada, FL

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

December - February
High 81°F       Low 56°F
March - May
High 87°F       Low 59°F
June - August
High 91°F       Low 74°F
September - November
High 90°F       Low 64°F

Top Attractions Around Islamorada, FL

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


Theater of the Sea
Bud n' Mary's Dive Center
Founders Park
Islamorada County Park
Hurricane Monument
Windley Key Fossil Reef Geological State Park
History of Diving Museum
Matecumbe United Methodist Church
Florida Keys Brewing Co.
John Pennekamp Coral Reef State Park
Jimmy Johnson's Big Chill
Dolphin Research Center
Key Largo Undersea Park
Dolphins Plus Bayside
Florida Keys Visitor Center
Dolphin Cove
Anne's Beach
Caribbean Club Bar
Dolphins Plus
Harry Harris Park

Other Places to Stay in Islamorada, FL


History of Diving Museum 956 Properties
Windley Key Fossil Reef Geological State Park 809 Properties
Seabreeze Trailer Park 805 Properties
Upper Matecumbe Key 793 Properties
Theater of the Sea 791 Properties
Matecumbe United Methodist Church 778 Properties
Plantation by the Sea 717 Properties
Coral Cove 636 Properties
White Marlin Beach 338 Properties
Toll Gate Shores 327 Properties
Venetian Shores 48 Properties
Lower Matecumbe Beach 26 Properties

Frequently Asked Questions About Islamorada?

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

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

Discover 249 accommodations with private or nearby pickleball courts in Islamorada. Some of the best destinations to stay and play pickleball are:

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

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

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 1522 properties listed in Islamorada 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 (9) 
Neighborhood Property Count
Venetian Shores Vacation Rentals in Islamorada, Florida 48
Lower Matecumbe Beach Vacation Rentals in Islamorada, Florida 26
Toll Gate Shores Vacation Rentals in Islamorada, Florida 327
Seabreeze Trailer Park Vacation Rentals in Islamorada, Florida 805
White Marlin Beach Vacation Rentals in Islamorada, Florida 338
Plantation by the Sea Vacation Rentals in Islamorada, Florida 717
Coral Cove Vacation Rentals in Islamorada, Florida 636
Plantation Lake Estates Vacation Rentals in Islamorada, Florida 709
Bonefish Bay Vacation Rentals in Islamorada, Florida 340

People Also Ask

There are 1522 Islamorada, FL Vacation Rentals

Recently Booked Vacation Rentals in Islamorada