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, 109 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

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

A stretch of sandy beach is lined with gentle waves, meeting the clear turquoise water. In the background, low-rise buildings and palm trees are visible, along with distant mountains under a partly cloudy sky.

4.86 out of 5 average rating, 44 reviews

NEW Double S Suite

In the heart of Simpsonbay, close to bars, restaurants, and the beach, you'll find this stylish and newly constructed apartment. Only 4 min from the airport and have double-paned windows to keep out the noise. The apartment has a queen-size bed, free Wi-Fi, and 2 flat-screen TVs; it's also only 2 minutes from Simpson bay beach, known for its clear water. This chic grey and white studio comes with all the amenities necessary for a restful and romantic beach getaway in the middle of St. Maarten.

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, 44 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.

4.87 out of 5 average rating, 209 reviews

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.

Apartment

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, 111 reviews

The open-concept living area features modern furniture, including a comfortable sofa and a dining table set for four. Large glass doors provide a clear view of the golf course and ocean, allowing natural light to fill the space. A stylish light fixture hangs above the dining table.

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

A tropical beach scene features a lone palm tree against a backdrop of clear turquoise waters and soft white sand. Light clouds float in a bright blue sky, creating a serene environment. Vegetation frames the sandy path leading to the water's edge.

Apartment

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.

4.92 out of 5 average rating, 63 reviews

A serene bedroom features a spacious bed dressed in light bedding with ocean-themed decorative pillows. On either side of the bed, stylish nightstands hold lamps. Above the bed, three framed artworks depict aquatic scenes. A potted plant adds a touch of greenery to the corner.

Apartment in Maho Beach

Turtle Den YOUR Maho Escape!

Welcome to Turtle Den, an enchanting ocean-inspired studio in the heart of Maho, St. Maarten. More than a stay, it's an immersive experience. Dive into a tranquil palette of oceanic hues, playful turtle motifs, and serene vibes. Just steps from Maho Beach, where planes land and take off, it's a front-row seat to breathtaking moments. Immerse in Maho's lively scene, surrounded by clubs and restaurants. Turtle Den is an invitation to savor the ocean's beauty and celebrate a world of whimsy.

An outdoor living area is highlighted by a dining table with four chairs, accompanied by a cozy built-in bench adorned with decorative pillows. Lush palms and vibrant greenery frame the view of the beach, while sunlight filters through the breezy overhead fan.

5 out of 5 average rating, 206 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 relaxing terrace is featured, overlooking the turquoise waters and lined with tropical foliage. Two comfortable seated chairs are positioned invitingly, beside a small table adorned with flowers. Nearby, sailboats can be seen gently swaying in the distance against the calm sea.

4.93 out of 5 average rating, 123 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 vibrant view of the lagoon is captured, with boats gently anchored along the shore. Palm trees frame the scene, and white fencing enhances the waterfront atmosphere. In the background, light-colored buildings with red roofs complement the natural beauty of the surrounding hills.

5 out of 5 average rating, 12 reviews

Condo in Simpson Bay

Location, Location, Location!! This delightful, newly renovated, centrally located Simpson Bay Yacht Club condo is yours to enjoy. A welcoming spacious one bedroom +Queen Sofa bed in living room. Private patio overlooking the lagoon. Two communal swimming pools / two tennis courts . 24-hour security for peace of mind. New A/C. Two designated parking spaces. Short walking distance to the beach, cafe's, supermarket, restaurant, bars and cinema.

4.99 out of 5 average rating, 81 reviews

An aerial view captures a scenic landscape where a wide, white bridge spans across a blue waterway. Sailboats dot the water, contrasting with lush green hills in the background, while the horizon meets the serene sea under a partly cloudy sky.

Apartment

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.

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Popular amenities for Simpson Bay vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Simpson Bay

4.84 out of 5 average rating, 92 reviews

A sandy beach is lined with lounge chairs and umbrellas, offering shaded spots for relaxation. The clear blue water stretches into the distance, with sunbathers and swimmers filling the shoreline. Nearby buildings are visible, contributing to the lively atmosphere of the beach.

Condo in Lowlands

Amenity-Filled Maho Studio, 5Mins to Airport/Beach

5 out of 5 average rating, 35 reviews

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.

Condo in Simpson Bay

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, 156 reviews

La Pearle - Luxurious 1 Bedroom Condo By the Beach

4.88 out of 5 average rating, 26 reviews

A modern kitchen area features a light wooden table set for dining, complemented by stylish grey chairs. Natural light floods the space through expansive glass doors, which lead to a patio with additional seating and views of the surrounding landscape and lagoon.

Apartment in Cole Bay

A101 - Outstanding Lagoon View & Garden

The image captures a serene beach scene at sunset, with gentle waves lapping at the shore. Several sailboats are anchored in the calm water, and soft clouds add depth to the colorful sky as the sun descends, reflecting light on the water's surface.

4.75 out of 5 average rating, 60 reviews

Sunshine, Sea & Sand - Apt 3

5 out of 5 average rating, 18 reviews

The image captures a serene shoreline with sandy beaches and clear turquoise water. Sailboats can be seen gently bobbing in the bay, with lush green hills in the background under a bright blue sky. Palm trees line the edge, adding to the coastal ambiance.

Condo in Marigot

New studio with superb view of the Caribbean Sea

5 out of 5 average rating, 12 reviews

A spacious covered terrace features a comfortable seating area with plush gray cushions, providing ocean views through large glass doors. Lush palm trees frame the scene, and a low coffee table complements the minimalist design, creating an inviting space for relaxation.

Condo in Simpson Bay

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.