277+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Trinidad and Tobago
  2. San Juan-Laventille
  3. Port of Spain

Port of Spain pickleball Stays, Resort Rentals, & Homes

About Port of Spain Vacation Rentals

Discover over 277 amazing vacation rental options in Port of Spain 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 Port of Spain.

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 456.8 ft², with prices averaging US $201 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 Port of Spain.

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Top Pickleball-Ready Accommodation Types in Port of Spain

Type Count
Holiday Apartments 132
Vacation Homes 73
Villas 12

Use these Quick Filters to Find a Vacation Rental in Port of Spain

★ 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 Port of Spain with PickleTrip™.

Top Attractions Around Port of Spain, TT

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


Movietowne
Queen's Park Savanah
Queen's Park Oval
Hasely Crawford Stadium
Holy Trinity Cathedral
Long Circular Mall
Brian Lara Promenade
Emperor Valley Zoo
Ariapita Avenue
Royal Botanical Gardens
Adam Smith Square
Woodford Square
President's House
Independence Square & Waterfront Park
Shops of Maraval
National Museum and Art Gallery
Queen's Hall
Ellerslie Plaza
Fort George

Other Places to Stay in Port of Spain, TT


Saint James 234 Properties
Maraval 226 Properties
Cocorite 226 Properties
St. Anns 207 Properties
Newtown 198 Properties
Westmoorings 165 Properties
Success 144 Properties
San Juan-Laventille 136 Properties
Downtown 89 Properties
Valsayn 42 Properties
San Juan 32 Properties
Woodbrook 24 Properties

Frequently Asked Questions About Port of Spain?

What are the top vacation rentals, resorts, and hotels in Port of Spain 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 Port of Spain. 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 Port of Spain!

How many pickleball-ready properties have private pools in Port of Spain?

Discover 5 accommodations with private or nearby pickleball courts in Port of Spain. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Port of Spain? 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 Port of Spain?

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 277 properties listed in Port of Spain 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 (3) 
Neighborhood Property Count
Downtown Vacation Rentals in Port of Spain, San Juan-Laventille 89
Cocorite Vacation Rentals in Port of Spain, San Juan-Laventille 226
Success Vacation Rentals in Port of Spain, San Juan-Laventille 144

People Also Ask

Finding the best prices in Port of Spain

There are 277 Port of Spain, TT Vacation Rentals

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