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, 173 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 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

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, 121 reviews

Sint Maarten La Terrasse Maho

It's a cozy large studio with a king size bed, a queen size sleeper sofa and a big balcony, it is at the second floor at Royal Islander Club Resort La Terrasse in Maho, fully equipped and furnished. Located just in front of Maho Bay beach and few minutes walk from Mullet bay beach. There are few restaurants and boutiques like cigar shops, jewelers and beauty store. Casino Royale is right next door. There are also a supermarket for grocery shopping, a pharmacy, a clinic and more...

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, 216 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 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

4.95 out of 5 average rating, 121 reviews

"SeaBird" studio, feet in the water on the beach

The "SeaBird studio" is ideally located with a beautiful view of the Caribbean Sea and an idyllic beach just for you! It offers plenty of comfort and storage with refined and original decoration. The residence is perfectly secure with a large swimming pool and tropical garden. Everything is within walking distance: grocery store, local market, shops, traditional or gourmet restaurants, ferry station to other islands, etc... High-speed Wi-Fi and TV Europe and America.

Top 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, 137 reviews

Cupecoy Garden Side 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

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, 164 reviews

Sea Loft, Breathtaking View – Private Pool

* 200 m² loft * Exceptional sea view * Private pool * 250 meters from the small beach of Galisbay * Terrace with deckchairs, garden furniture, outdoor table and BBQ * Office space * 100 Mbps WiFi * TV with thousands of channels from around the world * 250 m walk to Fort Louis de Marigot marina * 5 min walk to Marigot city center with its restaurants, shops and other stores * 5 min to the pier for Saint-Barth and Anguilla, and the taxi station

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.

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, 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

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, 185 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!

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, 140 reviews

VILLA JADE 2: WATERFRONT SUITE/POOL

VILLA JADE is a complex of 3 villas located in the bay of CUL DE SAC and its islets... VILLA JADE 2 is a spacious/sea view suite for 2 people on the water, with a private pool. The 3 villas are adjoining but very quiet and private. Your unique view is the sea... Direct access to the sea via a pontoon, and kayaks at your disposal.

Guest favorite

A beachfront view of the apartment is showcased, framed by lush greenery. Sunlight filters through the leaves, casting a gentle light on the sandy shore. Lounge chairs are situated on the beach, inviting relaxation beside the calm water.

Apartment in Simpson Bay

4.84 out of 5 average rating, 179 reviews

Apartment on the beach 2

Beach front apartment with beautiful ocean view and Simpson Bay beach is ready to welcome you! It is located in Simpson Bay, walking distance to the tourist area with many restaurants, bars, clubs, grocery store, spas, night clubs and much more!!! You’ll love my place because of the gorgeous view, the location and the ambiance.