248+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. The Valley
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Little Harbour pickleball Stays, Resort Rentals, & Homes

About Little Harbour Vacation Rentals

Discover over 248 amazing vacation rental options in Little Harbour 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 Little Harbour.

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 1776.3 ft², with prices averaging US $2,056 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 Little Harbour.

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Top Pickleball-Ready Accommodation Types in Little Harbour

Type Count
Villas 131
Holiday Apartments 45
Vacation Homes 38
Cottages 3

Use these Quick Filters to Find a Vacation Rental in Little Harbour

★ 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 Little Harbour with PickleTrip™.

Weather in Little Harbour, AI

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

December - February
High 83°F       Low 74°F
March - May
High 84°F       Low 75°F
June - August
High 87°F       Low 76°F
September - November
High 87°F       Low 77°F

Top Attractions Around Little Harbour, AI

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


Elsie Bay
Shoal Bay Beach
Meads Bay
Maundays Bay
Rendezvous Bay Beach
Meads Bay Pond
Barnes Bay
Cove Bay
Shoal Bay West
Sandy Island
Scilly Cay
Savanna Bay Beach
Scrub Island
Island Harbor Beach
Anguillan Christian Fellowship Church
Sandy Hill Beach
Little Bay
Captain's Bay Beach
Cheddie Richardson Carving Studio

Other Places to Stay in Little Harbour, AI


George Hill 203 Properties
Elsie Bay 186 Properties

Frequently Asked Questions About Little Harbour?

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

How many pickleball-ready properties have private pools in Little Harbour?

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

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

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

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 248 properties listed in Little Harbour 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 248 Little Harbour, AI Vacation Rentals

Recently Booked Vacation Rentals in Little Harbour