Beachfront holiday rental in Simpson Bay

5 out of 5 average rating, 8 reviews

Home in Lowlands

Sunset 2BR 2BH House in Cupecoy with Private Pool

This Brand New Luxurious town house is perfectly located in the sought after area of Cupecoy. Offering a perfect blend of comfort, convenience & Caribbean charm for a memorable stay that fits perfectly to your weekend getaways, staycation, or work from home This house will bring your Caribbean dream vacation come true. It is walking distance to the Cupecoy beach and just 5 minutes drive from MulletBay & Maho Beach It has a private plunge pool and a rooftop terrace with amazing lagoon views.

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.

4.81 out of 5 average rating, 182 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

4.96 out of 5 average rating, 140 reviews

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

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.

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.

4.88 out of 5 average rating, 233 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.

5 out of 5 average rating, 119 reviews

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

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!

4.95 out of 5 average rating, 125 reviews

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

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...

4.99 out of 5 average rating, 183 reviews

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

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

5 out of 5 average rating, 231 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

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.

5 out of 5 average rating, 143 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, it is not directly on the beach but 25 steps away. 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.

4.93 out of 5 average rating, 140 reviews

Le Petit Paradis - Beachfront 1 Bedroom Apartment

"Petit Paradis" (Little Paradise), a genuine Caribbean getaway. A spacious one-bedroom Beachfront apartment right on beautiful Simpson Bay Beach and in the center of all the happenings. Relaxing terrace, five stairs away from the Beach, and within walking distance from great Restaurants, Nightlife, Activities, and Watersports. This modern, fully furnished, and equipped apartment has everything you need for a dream vacation. Hope to invite you soon in our Paradise, Elodie

4.97 out of 5 average rating, 149 reviews

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

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.

4.91 out of 5 average rating, 116 reviews

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

«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

Popular amenities for Simpson Bay beachfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

4.86 out of 5 average rating, 152 reviews

A view of a sandy beach with crystal-clear turquoise waters. Gentle waves are visible lapping at the shore. A few boats can be seen in the distance against a backdrop of a bright blue sky dotted with fluffy clouds. Lush green foliage frames the scene.

Condo in Saint Martin

2 Bedroom Duplex up to 5 guests right on the beach

Apartment in SAINT MARTIN

A comfortable outdoor seating area is featured, consisting of a white sectional sofa and individual chairs, all accented with red cushions. A small table sits in the center, surrounded by lush greenery and a view of the beach in the background.

5 out of 5 average rating, 28 reviews

"Black Pearl"

5 out of 5 average rating, 74 reviews

The living area features floor-to-ceiling windows offering panoramic views of the lagoon and mountains. A comfortable blue sofa is complemented by textured cushions, with a cozy brown armchair nearby. A round table sits in the center, showcasing a remote control and decorative elements.

Apartment in Lowlands

Gorgeous 2 bedroom-17th floor, Fourteen Mullet Bay

5 out of 5 average rating, 59 reviews

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 in Grand Case

Charming apartment on the beach, 1 or 2 bedrooms

4.94 out of 5 average rating, 35 reviews

Apartment in Grand Case

Modern Apt in Beachfront residence - Hill view

4.93 out of 5 average rating, 122 reviews

Loft in Grand Case

Beachfront Loft in Grand Case - Sea View

4.76 out of 5 average rating, 134 reviews

Villa in Lowlands

SEA TRUE VILLA,Lavish,Sea view near Maho&Mulletbay

A white, modern condo complex is set atop a rocky outcrop overlooking a sandy beach. Waves gently lapping at the shore and a clear blue sky serve as a backdrop, creating a serene coastal atmosphere.

4.94 out of 5 average rating, 71 reviews

Coral Villa- Steps From BEACH!

Beachfront home rentals with a pool

5 out of 5 average rating, 20 reviews

A corner balcony with a stunning ocean view features two wooden chairs and a small coffee table. A patterned rug and natural decor elements are present, creating an inviting outdoor space. Floor-to-ceiling glass doors provide a seamless transition to the living area.

Apartment in Cupecoy

B1401 @ Fourteen, luxurious & cosy 2 bedroom apt

5 out of 5 average rating, 51 reviews

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

The Cliff in Cupecoy Beach HEAVEN!!!

Home in Collectivity of Saint Martin

A tranquil pool reflects the azure sky and distant boats. Surrounded by lush greenery, the pool area features a cascading waterfall and is bordered by smooth stones. A wooden partition provides privacy, enhancing the serene atmosphere of the waterfront retreat.

4.88 out of 5 average rating, 89 reviews

ALMOND BLUE ...Pinel bay view - caribbean feeling

A serene view of the property’s swimming pool surrounded by lush greenery and palm trees. Loungers are positioned along the poolside, providing spaces for relaxation. The turquoise waters of Simpson Bay are visible in the background, complemented by a clear blue sky.

4.89 out of 5 average rating, 62 reviews

Beachfront Paradise with Pool & Stunning Sunsets

5 out of 5 average rating, 9 reviews

Condo in Baie Orientale

NEW! Orient Bay's best view 2 bedrooms 2 bathrooms

Superhost

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.

4.86 out of 5 average rating, 36 reviews

Beacon Hill Hideaway: Luxury Condo in Simpson Bay

4.94 out of 5 average rating, 16 reviews

A spacious living area features floor-to-ceiling windows, allowing natural light to fill the space. Stylish blue chairs are arranged around a contemporary coffee table. A large piece of wall art adds a vibrant touch, and modern entertainment equipment can be seen in the background.

Condo in Cupecoy

Mullet Bay Suite 802 - Your luxury vacation in SXM

Condo in Collectivity of Saint Martin

5 out of 5 average rating, 20 reviews

Villa Bora Bora - Beach and Caribbean Sea

Private beachfront home rentals

A bright seating area is highlighted by large windows offering a view of the beach and palm trees. Two woven chairs surround a low coffee table, while a decorative woven cactus enhances the coastal theme. Light colors and wood accents create a welcoming atmosphere.

Condo in Collectivité de Saint-Martin

4.79 out of 5 average rating, 24 reviews

Casa sun Les vacances à la plage.

Villa in Simpson Bay

Sea breeze Villa right on Simspon bay beach

Apartment in Jordon Village

5 out of 5 average rating, 6 reviews

New ! Mullet Escape, walking to Mullet Bay Beach

Condo in Saint Martin,Guadeloupe

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.

5 out of 5 average rating, 60 reviews

Villa Belharra, amazing view

4.78 out of 5 average rating, 201 reviews

A spacious verandah features a comfortable seating area with a light-colored couch and a dark wicker coffee table. Lush greenery is displayed in a yellow planter, with panoramic views of the hills and bright blue sky in the background.

Home in Indigo Bay

La Pearle - Luxurious 1 Bedroom Condo By the Beach

5 out of 5 average rating, 17 reviews

An outdoor seating area features a white sofa and coffee table, surrounded by a glass railing. A panoramic view includes lush green golf course, sandy beach, and turquoise waters under a partly cloudy sky, creating an inviting space for relaxation.

Condo in Lowlands

Stunning Penthouse on Mullet Bay beach

Apartment in Collectivité de Saint-Martin

A wooden deck overlooks the sandy beach and crystal-clear sea. Two loungers are positioned for relaxation, complemented by a small table and chairs. The vibrant blue water meets a clear sky, enhancing the scenic views of the tranquil surroundings.

4.94 out of 5 average rating, 51 reviews

Nouveau un rêve sur la plage !

A living room area features comfortable seating with colorful cushions against light blue walls. A dining table is set with breakfast items, including orange juice and pastries. Large windows allow natural light to illuminate the space, providing a view of the terrace and surrounding greenery.