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Vacation rentals in Simpson Bay

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Simpson Bay vacation rentals

Gym
BBQ grill
Laptop-friendly workspace
Wifi
Air conditioning

Simpson Bay condominium rentals

Superhost
A balcony offers a stunning lagoon view, framed by sliding glass doors. Two armchairs are positioned around a small table, providing a cozy seating area. The landscape features rolling hills and a sparkling waterway, visible in clear daylight.
Condo in Cole Bay
4.83 out of 5 average rating, 12 reviews

B256 - Amazing Top Floor Apartment With Balcony

Top guest favorite
A bright building is showcased with orange-tiled roofs and white walls, surrounded by lush greenery and palm trees. The structure is positioned along the water's edge, with boats visible in the distance and an inviting view of the bay and surrounding landscape.
Condo in Simpson Bay
5 out of 5 average rating, 37 reviews

CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub

Superhost
A neatly arranged bed with plush pillows is complemented by two rolled towels placed artistically in the foreground. A vibrant flower and small treats are positioned nearby. A modern lamp and a sofa adorned with colorful cushions are visible in the background.
Condo in Lowlands
4.8 out of 5 average rating, 143 reviews

Convenient Studio Apt Near Airport, Beaches & Food

Top guest favorite
Two sun loungers are positioned on a sandy beach, accompanied by a small table holding a bottle of champagne and two glasses. A backdrop of clear blue water and gentle waves is visible, with a few green trees enhancing the tranquil setting.
Condo
5 out of 5 average rating, 50 reviews

Villa Belharra, amazing view

Top guest favorite
A serene beachfront view is presented through sliding glass doors, showcasing a private terrace with a small round table and two chairs. Palm trees gently sway in the breeze, framing the clear turquoise sea and sandy beach beyond.
Condo in Marigot
4.96 out of 5 average rating, 118 reviews

Studio «SeaBird» les pieds dans l’eau sur la plage

Top guest favorite
A scenic view reveals a large swimming pool surrounded by lounge chairs and colorful flower gardens. The sparkling blue ocean and a distant boat can be seen, under a bright sky with fluffy clouds. Palm trees gently sway in the breeze, adding to the tropical ambiance.
Condo in Lowlands
4.96 out of 5 average rating, 120 reviews

Sint Maarten La Terrasse Maho

Top guest favorite
A serene beach scene captures gentle waves lapping at the shoreline, where soft sand meets clear blue water. The sky is adorned with scattered clouds, creating an inviting atmosphere, while distant boats can be seen on the horizon.
Condo in Simpson Bay
5 out of 5 average rating, 26 reviews

Beach front Condo Simpson Bay beach

Superhost
A dining area is presented with a modern table surrounded by four black chairs. Above, a colorful artwork adorns the wall, complementing the vibrant decor. Two candles on the table add an elegant touch, while soft lighting from above enhances the welcoming ambiance.
Condo in Cole Bay
4.83 out of 5 average rating, 121 reviews

Convenient, Near Airport, Free Parking + Security.

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Simpson Bay oceanfront vacation rentals

Top guest favorite
A private pool is situated on a wooden deck, surrounded by lush greenery and palm trees. Sun loungers are positioned nearby, offering a view of the sea and distant boats. The clear water of the pool reflects the vibrant blue sky.
Villa in Collectivity of Saint Martin
5 out of 5 average rating, 79 reviews

VILLA I LOVE VIEW - villa luxe avec vue mer

Guest favorite
A clear glass of champagne rests atop a woven placemat, beside a vibrant vase filled with pink flowers. In the background, a stunning view of turquoise waters and lush green hills can be seen under a partly cloudy sky.
Cottage in Sint Maarten
4.92 out of 5 average rating, 106 reviews

«La Vue SXM» Luxe "Villa La Vue" + Beach/Bar/Food

Top guest favorite
A tranquil view of the Caribbean Sea is captured from a cozy sleeping area, featuring a spacious bed with light-colored linens. The scene is framed by flowing white curtains, leading to a covered terrace adorned with a thatched gazebo and beachside furniture.
Apartment
5 out of 5 average rating, 40 reviews

Charming apartment on the beach, 1 or 2 bedrooms

Guest favorite
A private balcony features a hammock and two modern chairs, inviting relaxation with ocean views. A striped rug complements the wooden flooring, and glass railing allows unobstructed sightlines to the water and surrounding beach area.
Loft
4.93 out of 5 average rating, 107 reviews

Mojito, Beachfront loft overlooking the sea

Superhost
The image depicts a clear blue swimming pool surrounded by lounge chairs and tropical palm trees. In the background, the ocean can be seen alongside a beach area with a white railing, under a bright sky featuring fluffy clouds.
Apartment in Simpson Bay
5 out of 5 average rating, 4 reviews

1-bdr condo in Beachfront Residence, Simpson Bay

Top guest favorite
A spacious living area is shown with large open doors leading to a private terrace. Light-colored furniture is arranged comfortably, with a dining table ready for meals. The ocean view is visible in the background, providing a serene backdrop to the inviting space.
Apartment in Grand Case
5 out of 5 average rating, 6 reviews

1 bd Grand-Case beach

Top guest favorite
A panoramic view of turquoise waters showcases numerous boats anchored in the distance, framed by lush palm trees. A rainbow appears across the sky, adding a colorful touch to the serene coastal landscape.
Townhouse in Cole Bay
5 out of 5 average rating, 99 reviews

Hillside Beach Townhouse Simpson Bay

Guest favorite
A lively beach promenade is visible, lined with palm trees and shaded umbrellas. Pedestrians can be seen walking along the path, while golden sandy beaches and vibrant blue waters create a scenic backdrop. Lush greenery and distant hills enhance the overall coastal view.
Apartment
4.92 out of 5 average rating, 119 reviews

Amazing "Colosseo" duplex ocean view

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Oceanfront condominium rentals in Simpson Bay

Top guest favorite
An inviting infinity pool is positioned adjacent to the shoreline, offering unobstructed views of the Caribbean Sea. Lush palm trees frame the scene, while the sun reflects off the water's surface, creating a serene atmosphere. The surrounding terrace features natural stone tiles.
Condo in Lowlands
5 out of 5 average rating, 45 reviews

The Cliff in Cupecoy Beach HEAVEN!!!

Guest favorite
A modern dining area features a white table surrounded by stylish black chairs. Large sliding glass doors open to a view of the sandy beach and turquoise waters, creating a seamless connection between indoor and outdoor spaces.
Condo in Baie Nettle
5 out of 5 average rating, 12 reviews

WHY NOT Splendid apartment right on the beach

Guest favorite
A spacious terrace is displayed, featuring comfortable seating arrangements and a dining table. The ocean view is unobstructed, framed by vibrant greenery. A hammock adds a touch of relaxation, while the light-colored flooring enhances the bright atmosphere of the space.
Condo in Orient Bay
4.83 out of 5 average rating, 101 reviews

Princess Anouk, Orient Bay, piscine, sur la plage

Guest favorite
A light-filled living area features two white sofas adorned with neutral and yellow throw pillows. A low coffee table rests on a textured rug between the sofas. A large window provides a clear view of the ocean, enhancing the serene atmosphere.
Condo
5 out of 5 average rating, 29 reviews

Ocean Sounds

Guest favorite
A spacious bedroom features a large window offering panoramic views of the ocean and nearby mountains. Two elegant chairs sit beside a small table, with a tray holding beverages and snacks placed on the bed. Natural light fills the room, creating a bright atmosphere.
Condo in Simpson Bay
5 out of 5 average rating, 16 reviews

Beacon Hill Hideaway: Luxury Condo in Simpson Bay

Superhost
A table set for breakfast is positioned against an ocean backdrop, featuring vibrant textiles. A fruit bowl holds bananas and pineapple alongside pastries, with glasses of orange juice. The calm sea and blue sky create a serene atmosphere, with greenery visible along the edge.
Condo in Grand Case
4.9 out of 5 average rating, 42 reviews

Paradis Caraibes 2BR * On the Beach!

Guest favorite
A view from the balcony showcases the sparkling ocean, with a rainbow arc illuminating the water. Below, one of the community pools is framed by loungers and lush greenery. A champagne bucket sits on the table, inviting leisurely relaxation.
Condo in Lowlands
4.92 out of 5 average rating, 37 reviews

Enjoy Stunning Sunsets Beachside 2 BR/2 Bath Condo

Guest favorite
A private terrace offers a view of the beach and sea, featuring comfortable outdoor seating including a hanging chair. The space is shaded by modern slats overhead, with a glass railing ensuring unobstructed views of the turquoise water and distant islands.
Condo
4.94 out of 5 average rating, 16 reviews

Beachfront Grand Case - Sea view - Brand new

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Quick stats about vacation rentals in Simpson Bay

  • Total rentals

    360 properties

  • Nightly prices starting at

    € 26 before taxes and fees

  • Total number of reviews

    11K reviews

  • Family-friendly rentals

    150 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with a pool

    240 properties have a pool

Frequently Asked Questions

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

    Simpson Bay has more than 150 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do condo rentals in Simpson Bay have self check-in?

    Absolutely! We offer over 20 condo rentals with self check-in in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

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

    Absolutely! We offer over 20 house 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 Villa Rentals in Simpson Bay?

    Enhance your stay in our Villa Rentals with the most popular amenities: over 30 homes with wifi, over 10 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 70 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 house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 house rentals 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 villa rentals in Simpson Bay?

    Experience the best of Simpson Bay with our villa rentals, starting at about $170 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do serviced apartment rentals in Simpson Bay have wifi?

    Absolutely! We offer over 20 serviced apartment 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 50 apartment rentals with a gym in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

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