Vacation rentals in Simpson Bay

Guesthouse in Simpson Bay

A spacious terrace features a comfortable seating area with plush cushions. Lush greenery surrounds the space, offering a sense of tranquility. A staircase leads to an upper level. In the distance, a view of buildings and the sky is visible, enhancing the outdoor ambiance.

4.89 out of 5 average rating, 111 reviews

White Sands Beach Studio

This is the studio apartment you want. In a prime location in a safe neighborhood, with everything need to enjoy a perfect vacation. You have supermarkets, car rentals, restaurants, and bars within walking distance. A 30-second walk from Simpson Bay beach &6 min to Maho Beach, our world-famous airport beach. Public transportation is also available there. The apartment is recently renovated and equipped with AC, Netflix, a cozy kitchen, a magnificent garden, and a terrace overlooking the airport.

4.98 out of 5 average rating, 52 reviews

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.

Condo in Simpson Bay

OCEAN FRONT Steps From BEACH!

Step into our oceanfront paradise on Simpson Bay beach. Just steps away from the sandy coast! Cherish sunrise serenity and late-night tranquility. Relax on the patio, absorb vistas, let waves weave their soothing symphony – a cherished moment! : ) Great location too! Close to Sunset Beach Bar—grab an ice-cold Heineken, watch planes land above. Famous Maho is also a quick stroll (5min from Sunset Bar). food, shops, nightlife, casinos its all there. A perfect location to properly discover SXM!

A bright living area features large glass doors that open to a private outdoor space. A comfortable sofa and a coffee table are positioned on a light-toned rug. A TV is mounted on a sleek white cabinet, while wooden accents add warmth to the design.

5 out of 5 average rating, 45 reviews

The Loft at Simpson Bay Yacht Club

Welcome to The Loft at SBYC. Located in the heart of Simpson Bay in walking distance to the beach, great restaurants, grocery stores, shopping, salons/spas and more. In this fully renovated loft-style apartment, you will find high quality amenities throughout including a European kitchen and an amazing rainfall shower. The SBYC property offers 3 swimming pools, a hot tub, tennis courts and plenty of outdoor space for relaxing, all under 24-hour gated security. Free concierge service included.

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.

4.87 out of 5 average rating, 211 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.

4.91 out of 5 average rating, 115 reviews

A spacious bedroom features a large bed adorned with white linens and a soft gray throw. Three framed black-and-white prints are displayed on the wall above the bed, while a window offers views of the beach and ocean beyond.

Condo in Lowlands

Modern Oceanview 2-Bedroom Condo on Mullet Bay

Welcome to Fourteen, one of the most luxurious beachfront residences in St Maarten located directly on the famous Mullet Bay beach and golf course. Located on the 9th floor, You will find this spacious 2 bedroom condo offering beautiful ocean views, great for a group, family, or romantic getaway. Indulge yourself in all of the amenities, outstanding concierge services and dining experience Fourteen has to offer. We aim to make your stay unforgettable. $5 per night resort fee not included

A dining area features a modern table with four chairs, positioned near large windows showcasing panoramic views of the turquoise sea and sandy beach. A wall mirror reflects the inviting atmosphere, while lush greenery can be seen outside, enhancing the coastal ambiance.

4.96 out of 5 average rating, 199 reviews

Lilly's Beach

This is a very SPECIAL SMAll RESIDENCE known as Ocean Edge . Beach Front located directly on beautiful Simpson Bay Beach! Enjoys one of the best locations on the island . Panoramic sea views with your toes in the sand and balmy Caribbean breezes. A clear turquoise sea dazzles in tropical sun, powdery white sands stretching along one of St. Maarten's longest beaches. Apartment with modern amenities and comforts. A perfect vacation spot ! Back up system installed to insure electricity.

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.

5 out of 5 average rating, 208 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

4.96 out of 5 average rating, 69 reviews

A hanging chair with a patterned cushion is positioned beside a sparkling swimming pool, overlooking the expansive azure ocean. The clear sky displays a few fluffy clouds, enhancing the serene coastal view.

Villa in Simpson Bay

Waterfront "Bonjour" Beacon Hill St Maarten

This stunning 4-bedrooms, 4 bathrooms villa overlooks Maho Bay and provides a front row seat to beautiful SXM sunsets, and over the famous Maho Beach. Enjoy the views while taking a dip in the home’s infinity pool overlooking the ocean or from its multiple outdoor dining and seating options conveniently and securely located minutes from restaurants, bars, nightlife, Maho Market and more, steps away from direct beach access to Simpson Bay Beach. Back up Diesel Generator

Home in Upper Prince's Quarter

A modern kitchen and living area are visible, featuring a large island with bar seating, complemented by pendant lighting. Floor-to-ceiling glass doors provide access to an outdoor terrace with ocean views. Natural light fills the space, enhancing the contemporary decor.

5 out of 5 average rating, 10 reviews

Aman Oceanview

The Aman Oceanview is an oasis of calm, luxury and elegance, built into the hillside overlooking the sublime and sparkling Atlantic Ocean and Saint Barth. This a brand new modern property consists of two master bedrooms with two bathrooms, living room with fully equipped kitchen, exterior terrace and laundry area. All two bedrooms, the living room have unobstructed views of the ocean. A breathtaking infinity pool and a sundeck overlook the ocean, form the focal point of Aman

4.99 out of 5 average rating, 157 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, Breathtaking View – Private Pool

* 200 m² loft * Exceptional sea view * Private pool * 250 meters from the small beach of Galisbay * Terrace with lounge chairs, garden furniture, outdoor table and BBQ * Office area * 100 Mbps Wi-Fi * 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, boutiques and other shops * 5 min to the pier for Saint-Barth and Anguilla, and the taxi station

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, 134 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.

4.99 out of 5 average rating, 151 reviews

A private heated pool is featured at the edge of the terrace, offering views of the ocean and nearby islands. The clear blue water contrasts with the light-colored stone surrounding the pool, while lush greenery can be seen in the background against a clear sky.

Apartment in Little Bay

Stunning 2 BD Ocean View - Terraces Lt Bay

Treat yourself to the utmost stylish and modern ocean view apartment located in the exclusive Little Bay Hill . This spacious environment, is designed to be enjoyed as a family, has a terrace with stunning sea views, private pool, one master suites ( Japanese king bed and a walking closet), one bedroom suite with two twin size beds ( could be converted to king size bed ) . Welcome to Terraces Little Bay !

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Popular amenities for Simpson Bay vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Simpson Bay

Superhost

A serene view of the Caribbean Sea is captured, displaying vivid turquoise waters under a bright blue sky with fluffy white clouds. Palm trees are positioned on the left, gently swaying in the ocean breeze, complementing the tranquil beachfront setting.

4.93 out of 5 average rating, 15 reviews

SeaWaves Beachfront 1 Brm Apt with Generator

4.92 out of 5 average rating, 12 reviews

A panoramic view of the turquoise sea is captured from the rooftop, with the coastline and palm trees visible in the foreground. Soft white clouds drift over the lush green mountains in the distance, creating a serene backdrop to the vibrant scene.

Home in Simpson Bay

Townhouse Villa LX

Guesthouse in Simpson Bay

A modern two-story apartment structure features a covered balcony with seating for two. The exterior includes colorful accents and is surrounded by lush greenery. The parking area is enclosed by a wooden fence, accommodating multiple vehicles beneath the home.

4.96 out of 5 average rating, 100 reviews

Simpson Bay Beach 1 bed Apt Topdeck. Ocean views

Superhost

Lounge chairs are positioned beside an infinity pool that blends with the ocean horizon. A round lantern provides soft illumination. The scene captures a stunning sunset sky filled with soft colors and clouds, while a sailboat drifts peacefully on the water.

4.88 out of 5 average rating, 8 reviews

ANCHOR HOUSE - OCEANFRONT - MODERN & LUXURY STYLE

Superhost

Apartment in Grand Case

5 out of 5 average rating, 3 reviews

1 bd Grand-Case beach

4.97 out of 5 average rating, 68 reviews

A well-maintained outdoor pool is surrounded by lounge chairs, offering a relaxing space for guests. Shade is provided by large umbrellas, and tropical palm trees are visible in the background. The pool area is complemented by modern residential buildings, enhancing the serene environment.

Condo in Lowlands

Brand New- Maho Condo Studio with Seaview and Pool

Home in Upper Prince's Quarter

An outdoor lounge area features a modern pergola with plush seating and neatly arranged towels. The infinity pool, with its seamless edge, reflects the vibrant blue of the ocean under a clear sky, providing expansive views of the coastline and surrounding landscape.

4.96 out of 5 average rating, 48 reviews

Teresa’s Ocean Paradise