A coastal town with a marina, mountains in the background, and a clear sky.

Vacation homes in Simpson Bay

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Vacation homes in Simpson Bay

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a vacation rental stay in Simpson Bay on Hotels.com. These Simpson Bay vacation rentals consistently deliver on quality, location and traveler experience. Last updated on October 21, 2026.

A modern living room with a large glass door leading to a balcony overlooking the sea.

A bedroom with a large window offering a view of a beach and ocean.

A room with a large window overlooking a beach and ocean, a table with a bottle of champagne, and a book.

A modern living room with a large window overlooking the ocean, a dining area, and a kitchen with white cabinetry.

1. Fourteen at Mullet Bay

Maho

A resort with a view of sailboats on the water, a beach with palm trees, and a modern building with balconies.

A modern outdoor bar area with a pool, bar stools, and a view of the pool.

A hotel pool area with lounge chairs, a covered seating area, and a sign for 'Calama'.

A beach with lounge chairs and a thatched umbrella.

2. Hilton Vacation Club Royal Palm St. Maarten

Simpson Bay

CNY1,074

CNY1,303 total

includes taxes & fees

Oct 27 - Oct 28

A modern pool area with a view of the ocean, surrounded by palm trees and lounge chairs.

A modern living room with a sofa, ottoman, and dining area, a kitchen island with a sink, and large windows with a view of the ocean.

A modern kitchen with a central island, two bar stools, built-in appliances, and recessed lighting.

A lush green landscape with palm trees and a view of distant mountains.

3. Panorama Residences at Monte Vista

Point Blanche

A modern living room with large windows, a purple sofa, and a view of the beach and ocean.

A modern living room with a glass table, blue sofas, and a view of the sea.

A modern hotel room with a large bed, a view of a beach and golf course, and a balcony with seating.

A modern living room with a large sofa, a coffee table, and a TV on a cabinet. The room has large windows with a view of a cityscape and greenery.

4. Mullet Bay Suites: Your Luxury Stay Awaits

Maho

CNY1,711

CNY2,399 total

includes taxes & fees

Oct 22 - Oct 23

A high-rise hotel with a view of the sunset over a marina.

A multi-story hotel with a central courtyard, balconies, and a variety of shops on the ground floor.

A spacious living area with a central table, a sofa, and a staircase.

A marina with boats, a white building with a red dome, and a hillside with houses.

5. Simpson Bay Suites

Simpson Bay

CNY902

CNY1,010 total

includes taxes & fees

Oct 27 - Oct 28

A view from inside a building looking out to a beach with clear turquoise water and a distant ship.

A hotel room with two beds, a chair, a small table, and a potted plant.

A modern living room with a grey sofa, a small dining table, and a refrigerator.

A hotel room with two beds, a television, a small table, and a door leading to a balcony.

6. MIDTOWN MOTEL SXM

Downtown Philipsburg

CNY487

CNY585 total

includes taxes & fees

Oct 26 - Oct 27

A modern living room with a large sliding glass door leading to a balcony with a view of a coastal town and mountains.

A balcony with two wooden chairs and a small table, overlooking a marina with boats and a mountainous town in the background.

A modern living room with a sofa, coffee table, and chairs, overlooking a scenic harbor and mountains.

A modern kitchen with a dining area, a sofa, and a view of the mountains.

7. The Hills Residence

Simpson Bay

CNY1,023

CNY1,718 total

includes taxes & fees

Oct 21 - Oct 22

A spacious living area with a dining table, chairs, sofas, a TV, and a ceiling fan.

A beach with a pier extending into turquoise waters, a sandy beach with umbrellas, and a hillside with buildings in the background.

A multi-story hotel with balconies and air conditioning units.

8. Sea Palace

Downtown Philipsburg

A hotel room with a bed, a sofa, a small round table, and a chair. There is a bathroom visible through an open door.

A spacious lobby with a reception desk, seating area with sofas and chairs, a coffee machine, and a refrigerator.

A modern dining area with a mix of yellow and green chairs, a central table, and a ceiling with wooden panels and hanging lights.

A hotel room with a bed, a sofa, a rug, and a patterned wall.

9. July Apartments

Madame's Estate

CNY716

CNY752 total

includes taxes & fees

Oct 21 - Oct 22

A clear blue sky, a swimming pool with a view of the sea, and a hillside with buildings.

A person standing by a large window with a view of a body of water and a distant shoreline.

A hotel room with a bed, a chair, a hammock, and a view of the ocean.

A balcony with a table set for two, overlooking a beach with clear blue waters and a distant shoreline.

10. condostmaarten by the sea -Adults Only-

Indigo Bay

CNY2,306

CNY3,328 total

includes taxes & fees

Oct 21 - Oct 22

A rooftop pool area with lounge chairs, a small pool, and a view of sailboats at sunset.

A modern living room with a white sofa, a round dining table with chairs, a kitchen area with white cabinets and appliances, and a wooden ceiling.

A modern kitchen with a central island, bar stools, a potted plant, and a wooden door.

A covered outdoor seating area with wicker furniture, a hanging chair, and a view of the sea with boats.

11. Tradewinds at Simpson Bay

Simpson Bay

A beach with clear turquoise waters, a sandy shore, and a rocky cliff with vegetation.

A balcony with white furniture, a view of the ocean, and a clear sky.

A spacious living area with a view of the sea, furnished with sofas and a coffee table.

A resort pool area with palm trees, umbrellas, and a view of the ocean.

12. The Cliff

Maho

A bedroom with a bed, a TV mounted on the wall, a small fridge, and a bedside table with a lamp.

A bathroom with a toilet, sink, and shower.

A bedroom with a bed, curtains, a TV, an air conditioner, and a small cabinet.

A bathroom with a toilet, sink, and mirror.

13. Philips Scott House Calinago

Downtown Philipsburg

CNY1,023

CNY1,561 total

includes taxes & fees

Oct 21 - Oct 22

A narrow pathway flanked by lush greenery and a building with a white facade.

A wooden deck with a bench, overlooking a swimming pool surrounded by lush tropical vegetation.

A modern living room with a grey sofa, a small table with a plant, and a kitchen area visible through a glass door.

A pool area with lounge chairs and palm trees.

14. Cozy one-bedroom & mezzanine apartment

Point Blanche

A pool area with a view of the ocean, a table with chairs, and a bench with orange cushions.

A modern living room with a sofa, chairs, a dining table, and a large window.

A balcony with a view of the ocean, a white railing, and two lounge chairs.

A modern living room with a glass dining table, white chairs, a sofa with orange cushions, and a ceiling fan.

15. Sapphire Fatastic

Maho

A swimming pool with blue tiles, surrounded by white walls and blue lounge chairs.

A balcony with a view of a residential area, including houses with red roofs and a body of water in the distance.

A modern living room with a flat-screen TV, a small table with a toaster, a wicker chair, and built-in shelving.

A two-story building with a brown wooden door and steps leading to a balcony.

16. Tamarind Hotel Suite

Point Blanche

A coastal hotel with multiple white buildings, palm trees, and a clear view of the turquoise ocean.

A coastal resort with multiple white-roofed buildings, a clear blue sea, and a rocky shoreline.

A spacious living area with a high ceiling, a dining table, and a staircase leading to a balcony with a view of the sea.

A pathway lined with palm trees leading to a white building with balconies overlooking a beach.

17. Cupecoy Beach Club

Maho

A coastal resort with a marina, palm trees, and a clear view of the ocean.

A modern dining area with a glass table, black chairs, and elegant chandeliers.

A modern bedroom with a large bed, a TV, and a view of the sea.

A modern poolside area with a clear view of the sea, a blue building, and a separate glass structure.

18. Serenity Penthouse - The Pinnacle of Luxury

Maho

A deck with a pool, lounge chairs, and a table set for dining.

A modern living room with a glass coffee table, white sofas with blue cushions, and a large sliding glass door leading to an outdoor deck with a view of the sea and hills.

A view through a window of a building with a white railing, palm trees, and a sunset over the ocean.

A hotel room with a bed, a glass door leading to a balcony with a view of the sea, a mounted TV, and a wall with a collage of photos.

19. Cliff House

Simpson Bay

A bathroom with a shower, a window with blue-tiled walls, and a patterned rug.

A pool with clear blue water, surrounded by blue lounge chairs and a palm tree.

A room with a teal sofa, a small white table, and a wall painting of a beach scene.

A balcony with two wicker chairs and a small table, overlooking a beach with clear turquoise water and a ship in the distance.

20. Villas on Great Bay Beachfront Villa Foxie

Downtown Philipsburg

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Top neighborhoods in Simpson Bay

Pelican Key

A beach with thatched umbrellas, a pier, and boats in the background.

A beach with clear turquoise water, palm trees, and beach umbrellas. There are buildings with blue and white exteriors in the background.

A marina with a dock, a small white building, and a sailboat in the water.

A marina with several sailboats docked near a rocky shoreline and a beach in the background.

A sunset over a harbor with several boats and a large cloud formation.

Pelican Key

The Pelican Key neighborhood offers attractions such as Hollywood Casino and Flamingo Beach.

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Top landmarks in Simpson Bay

A wooden pier extending into calm waters with sailboats anchored nearby.

Kim Sha Beach

8.8/10 (591 reviews)

If being by the water is a major draw, Kim Sha Beach is a spot you might want to check out, located 0.3 mi (0.5 km) from central Simpson Bay. If you want to continue walking by the waves, head to Flamingo Beach and Lay Bay Beach, both within a short walk.

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Hollywood Casino

8.2/10 (583 reviews)

Looking to hit the casinos? Why not spend the evening at Hollywood Casino in Pelican Key to find out if luck is your lady. Hotels.com travelers also say the area is great for couples and has lots of nice beaches.

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Simpson Bay Beach

9.2/10 (1,834 reviews)

When the beach is calling your name, you might want to head down to Simpson Bay Beach, located 1 mi (1.6 km) from central Simpson Bay. If you want to continue walking by the waves, head to Maho Beach located nearby.

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Flamingo Beach

9.0/10 (768 reviews)

If want to top up your tan, you might want to head out to Flamingo Beach, located 0.5 mi (0.8 km) from central Simpson Bay. If you want to continue walking by the waves, head to Kim Sha Beach and Lay Bay Beach, both within a short walk.

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Lay Bay Beach

8.4/10 (212 reviews)

Whether you want to hunt for sand dollars or smell the fresh air, Lay Bay Beach is a spot you might want to check out, located 0.7 mi (1.1 km) from central Simpson Bay. Enjoy the sunset by the shore at Flamingo Beach, Kim Sha Beach, and Burgeaux Bay Beach, all 3 within a short walk.

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Dunes Casino

8.0/10 (249 reviews)

Hoping to do some gaming? Try your luck at Dunes Casino when visiting the center of Beacon Hill. Hotels.com travelers also say the area is family-friendly and has lots of nice beaches. It's also full of great shops and restaurants, so you can spend the afternoon having a wander.

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Market Garden Supermarket

9.4/10 (8 reviews)

If you like shopping, take time out to go to Market Garden Supermarket when in Simpson Bay.

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Learn more about Simpson Bay

Admired for its live music and entertainment, Simpson Bay features attractions such as Kim Sha Beach and Flamingo Beach. This beachside city has something for everyone including its casinos, restaurants, and sights like Hollywood Casino and Simpson Bay Beach.

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About the destination

Simpson Bay is a romantic destination known for its restaurants and bars. Hunt for sand dollars at Kim Sha Beach and Flamingo Beach. Popular sights in the surrounding area include Maho Beach.

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