Beachfront vacation rentals in Simpson Bay

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Top-rated beachfront rentals in Simpson Bay

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Guest favorite

A cozy living area features a comfortable gray sofa and a wooden coffee table. Two windows offer expansive views of the ocean, with light reflecting off the water. Beams stretch across the ceiling, enhancing the airy feel of the space.

Condo in Simpson Bay

4.8 out of 5 average rating, 171 reviews

Oceanfront w Pool | Maho Beach area

Location , Location Location ! You can not get any closer to the ocean than in this cliff side apartment. The sound of waves crashing below and incredible ocean views from every room. The sunrise is magical everyday and by night the glowing lights of Simpson bay. This cliff side apartment has everything you need for a dream stay away from the crowds. . Just steps from 4 beaches Simpson bay, Mullet bay, burgeux bay and a 5minute walk to the world famous Maho Beach with its famous plane landings

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

Le « studio SeaBird » est idéalement situé avec une vue magnifique sur la mer Caraïbes et une plage idyllique rien que pour vous! Il offre beaucoup de confort et de rangement avec une décoration raffinée et originale. La résidence est parfaitement sécurisée avec une grande piscine et jardin tropical. Tout est accessible à pied: épicerie, marché local, boutiques, restaurants traditionnels ou gastronomiques, gare maritime vers les autres îles, etc... Wifi haut débit et télé Europe et Amérique.

Guest favorite

A vibrant blue gate opens to reveal a sandy beach and calm waters. Decorative pots with blooming pink flowers frame the entrance, accompanied by lush green leaves. In the distance, sailboats can be seen on the horizon under a cloudy sky.

Apartment in Simpson Bay

4.87 out of 5 average rating, 214 reviews

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.

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, 101 reviews

Hillside Beach Townhouse Simpson Bay

Dreaming of a gorgeous sunset, turquoise waters and enjoyable nightlife? Welcome to Simpson Bay Beach Front Townhouse where sunny memories are made! Less than 1 minute walking (50meters) from the beach and surrounded by bars and popular restaurants featuring local and international food, spas, shops and casinos! Next to Simpson Bay Beach Resort and Marina where you have departures to different islands with numerous boat charter activities. The location assures that you will have an awesome!

Top guest favorite

An outdoor terrace features comfortable white lounge furniture arranged around a coffee table. Sun loungers are positioned beside a private infinity pool, overlooking the ocean and distant boats. The scene is framed by tropical plants and a clear blue sky, enhancing the serene coastal environment.

Loft in Marigot

4.99 out of 5 average rating, 163 reviews

Sea Loft Vue imprenable - piscine privée

* Loft de 200m² * Vue mer exceptionnelle * Piscine privée * A 250 mètres de la petite plage de Galisbay * Terrasse avec chaises longues, salon de jardin, table d'extérieur et BBQ * Espace bureau * Wifi 100 Mbps * TV avec milliers de chaines du monde entier * A 250 m à pied de la marina Fort Louis de Marigot * A 5 min à pied du centre ville de Marigot avec ses restaurants, boutiques et autres commerces * A 5 min de l'embarcadère pour Saint-Barth et Anguilla, et de la station de taxis

Top guest favorite

Large glass sliding doors open to a sunny outdoor deck with views of the turquoise ocean. Comfortable lounge chairs and a dining table are visible among tropical palm trees. The living area features a soft gray couch and a wall-mounted TV, creating an inviting indoor space.

Apartment in Simpson Bay

5 out of 5 average rating, 214 reviews

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

Guest favorite

A spacious dining area features a wooden table set with a bowl of oranges. Natural light streams through large windows, illuminating the cozy seating area in the background. Green plants add vibrancy to the room, creating a welcoming, serene atmosphere.

Apartment in Lowlands

4.97 out of 5 average rating, 135 reviews

Cupecoy Côté Jardin 1

Delightful one bedroom appt. Fully furnished with mid century teak furniture. A spacious 70m2 space with large terrace in a mature tropical garden. A brand new fully equipped kitchen was added in October 2022. Located in trendy and safe Cupecoy. CJ1 is a quiet oasis to relax in the luxurious garden, or head for the the renowned beach of Mullet bay within a 3 minute walk. Supermarkets, gym yoga studio very close by. This is the place to be.

Top guest favorite

A scenic view is captured from a balcony, showcasing sandy beaches and turquoise waters. Palm trees are swaying gently in the breeze, framed by the white railing. The distant shoreline is visible, dotted with umbrellas and palm-covered structures, under a partly cloudy sky.

Apartment in Philipsburg

4.99 out of 5 average rating, 142 reviews

Hibiscus-Large 1 bed Beachfront apartment 1st flr

This modernly decorated apartment home is centrally located in the capital of the Dutch side, Philipsburg. The area is full of life during the day and quiet and relaxing in the evening. This home away from home will make your daydreams of island life a reality. Enjoy the lovely courtyard garden downstairs, relax on the balcony looking out to the beautiful garden and plan your day’s adventure on and around this dual nation Island.

Top guest favorite

A spacious terrace is presented with a wooden dining table surrounded by four chairs, complemented by a selection of fresh fruit. Sun loungers are positioned for relaxation, with a view of the turquoise water and sailboats visible in the distance.

Apartment in Simpson Bay

5 out of 5 average rating, 136 reviews

Simpson bay beach, spacious, beautiful views!

Amazing spacious 3 bedroom, 2 bathroom apartment with awesome location in the heart of Simpson Bay. location, location, location in the middle of it all. Right across the 2.5 mile beautiful Simpson Bay Beach. All the beach necessities are there to enjoy, beachchairs, snorkeling gear, fishing rod and even 2 kayaks. You can walk to many nearby restaurants, grocery stores and other shops. Public transportation is also steps away.

Superhost

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, 108 reviews

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

Located in private gated community Indigo Bay, minutes from beach. Villa has private infinity pool and is neighbored by large communal pool. Modern art déco 2 floor villa has 3 bedrooms, 3 full bathrooms, equipped kitchen, balcony, and terrace with ocean views. **Construction of new hotel began in Indigo Bay as of March 2025 which impacts the entire bay** Free : - Champagne on arrival - 1 Mid Housekeeping Services

Top guest favorite

A private outdoor area features a swimming pool surrounded by lounge chairs, with views of the water and distant hills. Palm trees provide shade, while a wooden structure offers a dining space. Natural stone tiles create a welcoming atmosphere, ideal for relaxation.

Villa in Cul-de-Sac

4.99 out of 5 average rating, 138 reviews

VILLA JADE 2 : SUITE PIEDS DANS L'EAU / PISCINE

VILLA JADE est un complexe de 3 villas situé dans la baie de CUL DE SAC et ses îlets ... VILLA JADE 2 est une suite spacieuse / vue mer pour 2 personnes les pieds dans l'eau, avec piscine privée. Les 3 villas sont mitoyennes mais très calmes et intimes. Votre unique vue est la mer... Accès direct à la mer par un ponton, et kayaks à votre disposition.

Superhost

An inviting infinity pool stretches toward the horizon, offering uninterrupted views of the ocean and coastline. A covered terrace with two lounge chairs is positioned nearby, framed by a modern architectural structure that enhances the surrounding scenic beauty.

Home in Indigo Bay

4.83 out of 5 average rating, 183 reviews

Préstige - Luxurious 3 bedroom by the Beach

Nestled on the hills of Indigo Bay, Préstige is located midway between Philipsburg and the Simpson Bay touristic hangout. Préstige exudes relaxation the minute you walk through the door, elegant and distinguished! The 3-bedroom spacious residence sleeps six! Overlooking Indigo Beach with private swimming pool! Caribbean living, yours to enjoy!