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.

4.9 out of 5 average rating, 115 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.

4.8 out of 5 average rating, 172 reviews

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

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

4.98 out of 5 average rating, 55 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

Coral Villa- 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, 50 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.

4.91 out of 5 average rating, 120 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

5 out of 5 average rating, 101 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!

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, 201 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, 215 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, 73 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

4.99 out of 5 average rating, 164 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 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

4.99 out of 5 average rating, 153 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 !

4.95 out of 5 average rating, 106 reviews

An inviting outdoor space features a private pool surrounded by lush greenery and sea views. Comfortable lounge chairs are positioned nearby, providing a serene spot to relax. Sunlight reflects off the water's surface, creating a tranquil atmosphere.

Apartment in Indigo bay

Independent apartment at the bottom of the villa – Indigo Bay

The Villa Stella apartment welcomes you in a unique setting with spectacular views of the Caribbean Sea. Located in a 24-hour secure residence, tranquility awaits. You will be just an 8-minute walk to Indigo Bay Beach and close to shops and restaurants in the Dutch side. Composed of 2 bedrooms and 2 bathrooms, you can relax in the pool/jacuzzi overlooking the 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

Home in Upper Prince's Quarter

A spacious outdoor terrace features a stunning infinity pool overlooking the sea, complemented by comfortable sun loungers. A shaded dining area with a stylish table set for gatherings is visible, showcasing panoramic views of the coastline and vibrant blue ocean.

4.94 out of 5 average rating, 17 reviews

Breathtaking view of St Barth – 8 people

5 out of 5 average rating, 60 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

Superhost

An outdoor terrace is presented with lush green grass, featuring modern seating arranged around a wooden table. Soft furnishings and decorative pillows are positioned for comfort, while stunning views of the water and surrounding hills create a serene backdrop.

Apartment in Cole Bay

4.85 out of 5 average rating, 33 reviews

A101 - Outstanding Lagoon View & Garden

Home in Upper Prince's Quarter

A spacious bedroom is showcased with a large bed featuring neutral-toned linens. A panoramic window offers stunning views of the ocean and coastline, framed by soft drapes. A bedside table holds a lamp, and a television is positioned across the room, enhancing the modern decor.

5 out of 5 average rating, 63 reviews

Endless Views @ Acqua Bleu

5 out of 5 average rating, 7 reviews

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

1 bd Grand-Case beach

Townhouse in Sint Maarten

An inviting outdoor living space features a covered terrace with comfortable seating, a stylish bar area, and potted plants. The warm wooden flooring complements the soft purple lighting, while ocean views can be seen in the background, creating a relaxing ambiance for gatherings.

5 out of 5 average rating, 81 reviews

Indigo Bay Villa Poolside - Ocean 14

A vibrant ocean view is framed by lush green foliage. The tranquil turquoise waters of Simpson Bay are visible, with sandy beach and distant hills complementing the scene under a bright blue sky dotted with clouds.

5 out of 5 average rating, 11 reviews

Teal Bay Spacious Studio just minutes to the Beach

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.