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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
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!
$143 per night
Superhost
Apartment in Simpson Bay
Lilly's Beach
This is a very SPECIAL SMAll RESIDENCE known as Ocean Edge . Beach Front located directly on beautiful Simpson Bay Beach! Enjoys one of the best locations on the island . Panoramic sea views with your toes in the sand and balmy Caribbean breezes. A clear turquoise sea dazzles in tropical sun, powdery white sands stretching along one of St. Maarten's longest beaches. New totally refurbished modern apartment with modern amenities and comforts. A perfect vacation spot !
$239 per night

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Villas

Luxurious estates for the ultimate escape
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
Karakter Beach Bar/Restaurant48 locals recommend
Kim Sha Beach10 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
$197 per night
Superhost
Apartment in Simpson Bay
Unit 8 - Luxury apartment by the sea
$210 per night
Superhost
Condo in Simpson Bay
Hamaka condo, a beachfront retreat on Simpson Bay
$216 per night
Superhost
Apartment in Simpson Bay
The Bay at Palm Beach
$185 per night
Superhost
Apartment in Simpson Bay
SECOND HOME Beach Apartment
$119 per night
Superhost
Condo in Pelican
SeaLaVie Penthouse with Private Pool
$282 per night
Superhost
Apartment in Simpson Bay
Ocean's Edge
$204 per night
Superhost
Apartment in Simpson Bay
Modern apartment with pool
$150 per night
Superhost
Apartment in Simpson Bay
CocoVaa Boutique Hotel - Ruby Suite
$131 per night
Superhost
Hotel room in Lowlands
Hotel Studio with gym pool by Mullet Bay Beach
$111 per night
Superhost
Apartment in Cupecoy Beach
A-1002 Incredible 1 bedroom with a balcony
$231 per night
Superhost
Guesthouse in Simpson Bay
Simpson Bay Beach Apartment. Topdeck. Ocean View
$157 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 apartment rentals in Simpson Bay have a bbq area?

    Absolutely! We offer over 10 apartment 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 Serviced Apartment Rentals in Simpson Bay?

    Enhance your stay in our Serviced Apartment Rentals with the most popular amenities: over 20 homes with air conditioning, over 20 homes with wifi, 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 house rentals in Simpson Bay?

    Experience the best of Simpson Bay with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Simpson Bay have wifi?

    Absolutely! We offer over 20 house 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