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.

4.91 out of 5 average rating, 108 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, 169 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

An aerial view captures the lush landscape surrounding the waterfront property, featuring charming villas with red roofs, palm trees, and inviting swimming pools. The marina is visible with boats docked alongside, framed by a backdrop of rolling hills and a clear blue sky.

5 out of 5 average rating, 43 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 tranquil stretch of sandy beach is bathed in sunlight, bordered by gentle turquoise waves. Lush palm trees line the shore, with distant buildings visible against a backdrop of blue sky and scattered clouds. The beachfront invites leisurely walks or relaxing moments by the water.

4.87 out of 5 average rating, 207 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, 110 reviews

A view of a calm turquoise bay framed by swaying greenery, featuring several sailboats anchored in the water. The shoreline is dotted with low vegetation and a few structures are visible in the background under a bright blue sky with scattered clouds.

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

4.96 out of 5 average rating, 197 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.

4.96 out of 5 average rating, 115 reviews

An aerial view showcases a serene pool area surrounded by lounge chairs and umbrellas, with blooming tropical plants in the foreground. In the background, an airplane approaches the runway, framed by the vibrant blue waters of the Caribbean Sea.

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, 156 reviews

A spacious open-plan living area features high ceilings with exposed beams and large glass windows overlooking the sea. A wooden desk is positioned beside an elegant chair, while a comfortable sofa and armchair invite relaxation. Natural light fills the room, highlighting its inviting layout.

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

An outdoor seating area is showcased, featuring a cushioned bench adorned with decorative pillows. The space opens to a sunlit deck with lounge chairs, offering views of palm trees and the turquoise waters of Simpson Bay.

5 out of 5 average rating, 205 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 modern living area features a comfortable gray sofa and unique wooden coffee table. Natural light filters through the open shutters, revealing views of the turquoise water outside. A ceiling fan enhances airflow, and decorative elements add a touch of charm.

4.93 out of 5 average rating, 122 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

A sandy beach lined with palm trees leads to the clear blue water. Several beach chairs are visible in the foreground, while the apartment building with a blue roof is seen to the right, providing a serene coastal setting.

4.99 out of 5 average rating, 81 reviews

SECOND HOME Beach Apartment

Our SECOND HOME beach apartment is truly designed as a second home. A place to where we can escape from the world and reconnect with ourselves. It has all the amenities one needs, like a comfortable living room, high quality mattress and linens, cozy sitting on the terrace to watch the sunset, fully equipped kitchen, and airconditioning in each room. It is located just two houses away from the beautiful white sand beach of Simpson Bay.

Guest suite in Simpson Bay

An iconic aircraft approaches landing over a busy beach, where numerous beachgoers gather under green umbrellas. The shoreline is bordered by calm turquoise waters, with a backdrop of hotels and establishments. The sky is partly cloudy, enhancing the vibrant beachfront scene.

4.82 out of 5 average rating, 212 reviews

MYRIEL — Perfect Location/Nightlife/Beach

This Duplex 1 Bed apt is all about LOCATION. Nicest/Safest area of St.Maarten. Few steps from Simpson beach, Maho Beach nightlife/restaurants. 5-10mn walk on the beach to Karakter Beach bar and Sunset Beach Café. Very clean. Perfect for single or couple. Sleep up to 3 with sofa bed.. Private entrance, full kitchen, Stove, Microwave, A/C, WIFI, Linens and towels.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Popular amenities for Simpson Bay vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Simpson Bay oceanfront vacation rentals

Apartment in Cupecoy Beach

A spacious living area features large floor-to-ceiling windows, offering captivating views of the turquoise Caribbean sea and blue skies. A modern coffee table is set with a bowl of fruit and two glasses, complemented by soft drapes that frame the scenic backdrop.

4.91 out of 5 average rating, 69 reviews

A-1001 1 bedroom with incredible view

A spacious outdoor terrace is showcased with wooden decking and sun loungers beneath white umbrellas. The beach is directly accessible, with clear turquoise waters gently lapping at the shore. Lush greenery adds a natural touch to the scenic view, framed by bright blue skies and fluffy clouds.

4.94 out of 5 average rating, 82 reviews

Five Star Luxury Beachfront Condo Private Hot Tub

4.96 out of 5 average rating, 115 reviews

A private terrace features a round table and chairs, offering a view of the tranquil Caribbean beach and clear blue waters. Palm trees gently sway in the foreground, providing a serene backdrop to the picturesque shoreline and distant rocky outcrops.

Condo in Marigot

Studio «SeaBird» les pieds dans l’eau sur la plage

4.96 out of 5 average rating, 23 reviews

The living area features a cozy dark sofa adorned with decorative pillows and a soft throw. Two vibrant framed photographs are displayed on light blue walls, complementing the warm wood flooring. Natural light streams through the open door, enhancing the welcoming ambiance.

Apartment in Lowlands

Villa Spice For Life SXM 2

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, 133 reviews

Simpson bay beach, spacious, beautiful views!

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.

5 out of 5 average rating, 12 reviews

Beacon Hill Hideaway: Luxury Condo in Simpson Bay

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, 6 reviews

Spacious Studio just minutes to the Beach

Place to stay in Simpson Bay

A compact living area features a wall-mounted Murphy Bed that converts to a sofa, offering flexible space. A kitchenette with a refrigerator and sink is included. Natural light enters through an arched window, complementing the light-colored wood flooring and neutral furnishings.

4.95 out of 5 average rating, 20 reviews

The Hideaway

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Other great vacation rentals in Simpson Bay

4.89 out of 5 average rating, 9 reviews

A serene outdoor area is showcased, featuring a clear swimming pool with a jetted hot tub adjacent to it. The deck is lined with wooden planks, complemented by lush greenery in decorative planters. Views of the lagoon and surrounding hills are visible in the background.

Condo in Cole Bay

B256 - Amazing Top Floor Apartment With Balcony

A large swimming pool is surrounded by tall palm trees and lush tropical foliage. The clear blue water reflects the sunshine, creating a vibrant visual. A beautiful residence with a red-tiled roof is visible in the background, blending with the natural landscape.

5 out of 5 average rating, 35 reviews

CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub

A private verandah features a comfortable seating arrangement with wicker-style chairs and a low table. Beyond large sliding glass doors, an inviting interior area can be seen. The expansive ocean view showcases calm blue waters and a cloudy sky, creating a serene atmosphere.

Home in Indigo Bay

4.77 out of 5 average rating, 155 reviews

La Pearle - Luxurious 1 Bedroom Condo By the Beach

Apartment in SAINT MARTIN

5 out of 5 average rating, 10 reviews

Nouveau un Paradis sur la plage !

Villa in Indigo bay, Sint Maarten

A modern bathroom is presented, featuring tiled walls and a large mirror above a wooden vanity. A toilet is positioned to the side, while a glass shower enclosure allows for natural light. The space is complemented by a woven mat and neatly arranged toiletries.

5 out of 5 average rating, 20 reviews

Ocean Dream Villa

Apartment in Collectivité de Saint-Martin

The modern kitchen features sleek cabinetry and a wooden countertop, complemented by a dining area with a table and black chairs. Large glass doors allow natural light to flood the space while offering views of the serene beach and ocean beyond.

4.98 out of 5 average rating, 58 reviews

"Paradise Beach" - Impressive 2 bedrooms seafront

4.86 out of 5 average rating, 44 reviews

A modern living space features an open layout with large glass doors that provide views of palm trees. A sleek dining table is complemented by black chairs, while a light-colored sofa invites relaxation. Natural light illuminates the area, enhancing the airy atmosphere.

Apartment in Cole Bay

1 Bedroom- ocean view - Walk to beach - Generator