364+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Trinidad and Tobago
  2. Western Tobago
  3. Scarborough
  4. Diamond

Diamond pickleball Stays, Resort Rentals, & Homes

About Diamond Vacation Rentals

Discover over 364 amazing vacation rental options in Diamond 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 Diamond.

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 1073.84 ft², with prices averaging US $350 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 Diamond.

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Top Pickleball-Ready Accommodation Types in Diamond

Type Count
Villas 127
Holiday Apartments 112
Vacation Homes 73
Cottages 5

Use these Quick Filters to Find a Vacation Rental in Diamond

★ 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 Diamond with PickleTrip™.

Top Attractions Around Diamond, TT

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


Pigeon Point Beach
Turtle Beach
Store Bay
Englishman's Bay
Mount Irvine Bay
Pirate’s Bay
Buccoo Reef
Tobago Main Ridge Forest Reserve
Castara Beach
Dwight Yorke Stadium
Fort King George
Man-o-War Bay
Scarborough Botanical Garden
Royalton Casino
Stonehaven Bay
Buccoo Beach
Nylon Pool
Gulf City Mall
Tobago Museum
Grafton Caledonia Wildlife Sanctuary

Other Places to Stay in Diamond, TT


Lambeau 333 Properties

Frequently Asked Questions About Diamond?

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

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

Discover 59 accommodations with private or nearby pickleball courts in Diamond. Some of the best destinations to stay and play pickleball are:

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

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

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 364 properties listed in Diamond 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 364 Diamond, TT Vacation Rentals

Recently Booked Vacation Rentals in Diamond