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Waterfront holiday rentals in Simpson Bay

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Simpson Bay

Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

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Top guest favourite
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.
Flat in Simpson Bay
5 out of 5 average rating, 67 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.

Superhost
An infinity pool extends over the edge, offering panoramic views of the lagoon. The tranquil water reflects the blue sky, while steps lead from the pool's edge to the terrace. Lush greenery is visible, enhancing the serene atmosphere of the space.
Guest suite in Cupecoy
4.91 out of 5 average rating, 121 reviews

Panoramic View Terrace Infinity Pool Top Penthouse

Wake up to the magnificent panoramic view of the lagoon on the top floor, rejuvenate your body with a refreshing dip in the private rooftop infinity pool with a coffee or tropical drink. Take a 10 mins stroll to the famous Mullet bay Beach and grab a few freshly French croissants by the Square. After sunset, enjoy the plentiful neighborhood bars and restaurants or take 5 mins drive to Maho where you will find a vast variety of restaurants, casino and clubs or Porto Cupecoy for romance spot.

Guest favourite
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.
Apartment in Lowlands
4.92 out of 5 average rating, 134 reviews

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

Guest favourite
A serene beach view is captured, showcasing clear turquoise waters meeting powdery white sands. A picnic table sits on the beach, bordered by vibrant green plants and palm trees. Soft clouds drift above under a bright blue sky, completing the tranquil seaside scene.
Flat in Simpson Bay
4.95 out of 5 average rating, 220 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.

Top guest favourite
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.
Apartment in Lowlands
4.95 out of 5 average rating, 125 reviews

Saint 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...

Top guest favourite
Flat in Simpson Bay
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

Guest favourite
Flat in Simpson Bay
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

Top guest favourite
Apartment in Maho
4.91 out of 5 average rating, 237 reviews

Maho Love Shack:Unwind by the Rooftop Pool&Hot Tub

This charming, cozy, and tranquil tropical nest is located where all the action is! The golf course, iconic bars, the unprecedented landing strip, the popular Maho and Mullet bay beaches, Maho market with daily fresh take away breakfast/lunch buffets and a divine selection of exotic restaurants are all in walking distance. If you wish to just lounge and relax by the pool, jacuzzi, and private gazebo bar or enjoy the nightlife; it’s all readily available for you to indulge.

Top guest favourite
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.
Apartment in Marigot
4.96 out of 5 average rating, 140 reviews

"SeaBird" studio, feet in the water on the beach

The "SeaBird studio" is ideally located with a beautiful view of the Caribbean Sea and an idyllic beach just for you! It offers plenty of comfort and storage with refined and original decoration. The residence is perfectly secure with a large swimming pool and tropical garden. Everything is within walking distance: grocery store, local market, shops, traditional or gourmet restaurants, ferry station to other islands, etc... High-speed Wi-Fi and TV Europe and America.

Top guest favourite
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
4.99 out of 5 average rating, 183 reviews

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

Guest favourite
A bright living area features large glass doors opening to a waterfront view. Neutral-toned furnishings include a comfortable sofa and a unique wooden coffee table atop a circular area rug. Decorative greenery and modern art elements provide subtle accents against the white walls.
Flat in Point Pirouette
4.91 out of 5 average rating, 133 reviews

Secret View amazing apartment- Private pool

Welcome to Secret View! An elegant and intimate retreat with a private pool and a spacious terrace set directly on the lagoon. Designed for couples seeking calm, romance and discretion, just minutes from vibrant Maho with its restaurants, bars and casinos, and Mullet Bay Beach, one of the island’s finest beaches with stunning turquoise waters. Free private parking. This hidden gem is the perfect setting for unforgettable moments together.

Top guest favourite
A private outdoor area features a swimming pool surrounded by lounge chairs, with views of the water and distant hills. Palm trees provide shade, while a wooden structure offers a dining space. Natural stone tiles create a welcoming atmosphere, ideal for relaxation.
Villa in Cul-de-Sac
4.99 out of 5 average rating, 151 reviews

VILLA JADE 2: WATERFRONT SUITE/POOL

VILLA JADE is a complex of 3 villas located in the bay of CUL DE SAC and its islets... VILLA JADE 2 is a spacious/sea view suite for 2 people on the water, with a private pool. The 3 villas are adjoining but very quiet and private. Your unique view is the sea... Direct access to the sea via a pontoon, and kayaks at your disposal.

Popular amenities for waterfront rentals in Simpson Bay

When is the best time to visit Simpson Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$380 SGD$368 SGD$380 SGD$312 SGD$291 SGD$271 SGD$281 SGD$264 SGD$254 SGD$254 SGD$282 SGD$396 SGD
Avg. temp26°C26°C26°C27°C28°C29°C29°C29°C29°C29°C28°C27°C

Quick stats about waterfront rentals in Simpson Bay

  • Total holiday rentals

    Explore 130 holiday rentals in Simpson Bay

  • Nightly prices starting at

    Simpson Bay holiday rentals start at $103 SGD per night before taxes and fees

  • Verified guest reviews

    Over 5,360 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    70 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wifi availability

    130 of Simpson Bay holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Simpson Bay rentals

  • 4.9 Average rating

    Simpson Bay stays are highly rated by guests – averaging 4.9 out of 5!