Simpson Bay pickleball Stays, Resort Rentals, & Homes
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- 495 ft² Condo
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Luxury Places to Stay in Simpson Bay
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Top-Rated Villas with a Pool in Simpson Bay
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Pet-Friendly Villas in Simpson Bay
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Large Private Villas in Simpson Bay
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Wheelchair Accessible Holiday Homes in Simpson Bay
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Simpson Bay Villas, Airbnb and Holiday Homes Under $200
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- 1130 ft² Resort
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Instantly Bookable Villa Rentals in Simpson Bay
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Book a Last Minute Place to Stay in Simpson Bay
About Simpson Bay Vacation Rentals
Discover over 548 amazing vacation rental options in Simpson Bay 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 Simpson Bay.
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 870.05 ft², with prices averaging US $492 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 Simpson Bay.
Top Pickleball-Ready Accommodation Types in Simpson Bay
Type | Count |
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Holiday Apartments | 186 |
Villas | 109 |
Vacation Homes | 71 |
Cottages | 1 |
Use these Quick Filters to Find a Vacation Rental in Simpson Bay
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★ 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 Simpson Bay with PickleTrip™.
Weather in Simpson Bay, SX
View the weather forecast for Simpson Bay before booking your Simpson Bay Vacation Rentals to confirm your best time to go.
Top Attractions Around Simpson Bay, SX
PickleTrip offers a large selection of top attractions around Simpson Bay . Research things to do on your vacation before you visit Simpson Bay.
Other Places to Stay in Simpson Bay, SX
Frequently Asked Questions About Simpson Bay?
What are the top vacation rentals, resorts, and hotels in Simpson Bay 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 Simpson Bay. 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 Simpson Bay!
- SIMPSON BAY on beach 2 BR, 2.5 bath, panoramic ocean view, pool, GENERATOR
- Newly Renovated apartment with swimming pool and ocean view #3
- Beachfront Ultra Luxury - New Modern 2 Bed/2.5 Bath
- New! Apartment with swimming pool and ocean view #2
- Renovated Apartment with pool and ocean view#4
- Renovated Apartment with pool at the garden #6
- New ! Apartment with swimming pool and ocean view #1
- Anchor House - Direct Oceanfront - Luxury & Modern Style
- 3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at $225/nt!
- WOW! WOW! WOW!, NEW VILLA LIBRE` STUNNING INSIDE AND OUT!
How many pickleball-ready properties have private pools in Simpson Bay?
Discover 90 accommodations with private or nearby pickleball courts in Simpson Bay. Some of the best destinations to stay and play pickleball are:
- Paradise in the West Indies
- Luxury Oceanfront 3 Bedroom 3.5 Bathroom-Stunning Views of the Sea & Airport
- Bisou du Soleil - Oceanview Villa (Two Bedroom)
- Stunning ocean front villa
Which vacation rentals, resorts, or hotels in Simpson Bay is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Simpson Bay? 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.
- ENJOY THE BEAUTY OF ST MAARTEN BY STAYING RIGHT ON THE OCEAN IN LUXURY CONDO
- Villa Cleavage
- 46 m² Condo ∙ 1 bedroom ∙ 4 guests
How many PickleTrip vacation rentals or resorts are available in Simpson Bay?
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 548 properties listed in Simpson Bay 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 (2)
Neighborhood | Property Count |
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Maho Vacation Rentals in Simpson Bay | 462 |
Pelican Key Vacation Rentals in Simpson Bay | 96 |