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Vacation rentals in Simpson Bay

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Top-rated vacation rentals in Simpson Bay

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost
Apartment in Simpson Bay
Apartment on the beach
Let this tranquil, centrally located, 1 bedroom apartment become your home away from home. This beachfront property is located on the BEST and WIDEST stretch of Simpson Bay beach with gentle waves and no rocks, which makes it a perfect spot for swimming. Although this property is tucked away, and there are never many people on this part of the beach, it is in a heart of Simposn Bay. Simpson Bay beach offers one of the longest stretches of uninterrupted sandy, white coastline on Sint Maarten.
$160 per night
Superhost
Apartment in Simpson Bay
The Beach House Apartment
A stylishly modern one bedroom apartment directly located on the beautiful white sand beach of Simpson Bay. Enjoy the crystal clear waters by day and explore the Caribbean charm of our bustling nightlife. Our island getaway provides you with the full relaxation experience complete with beach chairs, umbrellas, outdoor shower, snorkel gear and paddle boards to complete beach side experience Amenities include free WIFI, kitchen, king size bed, beach chairs, umbrella's and much more
$295 per night
Superhost
Condo in Maho
2 Min to Beach/Exclusive Rooftop Jacuzzi, Pool+Bar
This charming, cozy, and tranquil tropical nest is located where all the action is! The golf course, iconic bars, the unprecedented landing strip, the popular Maho and Mullet bay beaches, Maho market with daily fresh take away breakfast/lunch buffets and a divine selection of exotic restaurants are all in walking distance! If you wish to just lounge and relax by the pool, jacuzzi, and private gazebo bar or enjoy the nightlife; it’s all readily available, at your fingertips!
$160 per night

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Villas

Luxurious estates for the ultimate escape

Houses

A space thats all yours, with room for everyone
Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Stay near Simpson Bay's top sights

Simpson Bay Yacht Club6 locals recommend
Sunset Bar and Grill29 locals recommend
Kim Sha Beach10 locals recommend
Karakter Beach Bar/Restaurant48 locals recommend
Casino Royale15 locals recommend
Sonesta Maho Beach Resort, Casino & Spa6 locals recommend

Other great vacation rentals in Simpson Bay

Superhost
Apartment in Simpson Bay
Le Petit Paradis - Beachfront 1 Bedroom Apartment
$150 per night
Superhost
Apartment in Simpson Bay
Unit 4 - Studio by the sea
$154 per night
Superhost
Condo in Simpson Bay
Hamaka condo, a beachfront retreat on Simpson Bay
$222 per night
Superhost
Apartment in Simpson Bay
SECOND HOME Beach Apartment
$109 per night
Superhost
Apartment in Simpson Bay
The Bay at Palm Beach
$193 per night
Superhost
Condo in Pelican
SeaLaVie Penthouse with Private Pool
$270 per night
Superhost
Apartment in Simpson Bay
Ocean's Edge
$173 per night
Superhost
Apartment in Simpson Bay
Modern apartment with pool
$150 per night
Superhost
Guesthouse in Simpson Bay
Simpson Bay Beach Apartment. Topdeck. Ocean View
$150 per night
Superhost
Apartment in Cupecoy Beach
A-1001 1 bedroom with incredible view
$218 per night
Superhost
Apartment in Simpson Bay
CocoVaa Boutique Beach Hotel - Diamond Suite
$281 per night
Superhost
Guesthouse in Simpson Bay
White Sands Beach Studio
$96 per night
Show all

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Simpson Bay?

    Simpson Bay has more than 140 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do apartment rentals in Simpson Bay have air conditioning?

    Absolutely! We offer over 100 apartment rentals with air conditioning in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

  • Do villa rentals in Simpson Bay have a bbq area?

    Absolutely! We offer over 10 villa rentals with a bbq area in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Simpson Bay?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with air conditioning, over 20 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there pet-friendly vacation rentals in Simpson Bay?

    Four-legged friends are welcome in Simpson Bay. Choose from more than 50 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Simpson Bay?

    Yes! Work meets play with ease at over 150 vacation rentals in Simpson Bay featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Simpson Bay vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 180 vacation homes with pools in Simpson Bay, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in serviced apartment rentals in Simpson Bay?

    Experience the best of Simpson Bay with our serviced apartment rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do villa rentals in Simpson Bay have wifi?

    Absolutely! We offer over 30 villa rentals with wifi in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Simpson Bay have a gym?

    Absolutely! We offer over 20 apartment rentals with a gym in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore