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House vacation rentals in Simpson Bay

Find and book unique houses on Airbnb

Quick stats about house rentals in Simpson Bay

  • Total vacation rentals

    Explore 20 vacation rentals in Simpson Bay

  • Nightly prices starting at

    Simpson Bay vacation rentals start at G$12,555 GYD per night before taxes and fees

  • Verified guest reviews

    Over 710 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Vacation rentals with a pool

    10 properties feature pools

  • Wi-Fi availability

    20 of Simpson Bay vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Simpson Bay rentals

  • 4.8 Average rating

    Simpson Bay stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated house rentals in Simpson Bay

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

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Top guest favorite
An open-plan living area showcases a modern kitchen with a marble countertop and sleek cabinetry. Large glass doors provide expansive ocean views and access to an outdoor terrace. A comfortable seating area includes neutral-toned furnishings, while dining space is set for meals with panoramic vistas.
Home in Upper Prince's Quarter
5 out of 5 average rating, 37 reviews

Sunrise Over St. Barths

BRAND NEW CONDO in a quiet gated community! "Sunrise Over St. Barths" is an oasis of luxury and elegance, built into the hillside overlooking the Atlantic Ocean and St Barth. Enjoy the sunrise every morning in this modern property consisting of 2 master bedrooms with 2 bathrooms, living room with fully equipped kitchen, exterior terrace and laundry area. Each bedroom and the living room have unobstructed panoramic views of the ocean. A breathtaking infinity pool and a sundeck overlook the ocean.

Guest favorite
The private patio features a saltwater pool with ocean views, complemented by lounge chairs and tropical plants. Soft clouds drift overhead, enhancing the serene atmosphere. Nearby, a dining area offers an inviting space for meals while overlooking the lush garden and the expansive sea.
Home in Cole Bay
4.85 out of 5 average rating, 40 reviews

Luxury Villa Turquoise Heaven in Pelican Key

Welcome to Villa Turquoise Heaven- Modern Luxury in Pelican Key, SXM Experience the pinnacle of Caribbean elegance at Villa Turquoise Heaven, the newest luxury villa in the exclusive Tepui Residence. Designed for relaxation and style, this modern retreat offers a seamless blend of indoor-outdoor living with unparalleled views of the turquoise Caribbean Sea. From waking up to the gentle sound of waves to savoring sunsets from your private infinity pool, Villa TH offers an unforgettable escape.

Top guest favorite
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.
Home in Upper Prince's Quarter
4.99 out of 5 average rating, 101 reviews

Endless Views @ Acqua Bleu

Nestled in the heart of Saint Martin, Acqua Bleu offers breathtaking views of turquoise waters and pristine beaches. You'll have direct access to some of the most gorgeous spots on the island, ensuring endless fun in the sun. You’ll enjoy access to various amenities, including a fully equipped kitchen, spacious living areas, a refreshing swimming pool, and much more! Acqua Bleu features two king bedrooms, each accompanied by a private bathroom. Get ready to enjoy a truly rejuvenating vacation!

Superhost
A serene outdoor space is framed by lush green palm leaves, leading to a tranquil swimming pool. Terracotta pots and a comfortable lounge area with plush cushions are visible, inviting relaxation in a natural setting surrounded by vibrant foliage.
Home in Cul-de-Sac
5 out of 5 average rating, 4 reviews

PALM BLUE Caribbean Pinel Bay View

Relaxez-vous aux Caraïbes dans cette superbe maison avec sa vue extraordinaire sur la baie de Pinel, élue 3ème plus belle destination des Caraïbes. Au milieu d'une réserve naturelle avec vue sur St Barthélémy, vous nagerez avec les tortues et les poissons exotiques. Avec un accès à la mer en contre-bas de la maison, vous profiterez des kayaks mis à disposition pour aller déguster une langouste ou un cocktail dans l'un des 2 restaurants sur l'ilet Pinel. St Martin - La perle des Caraïbes !

Top guest favorite
Home in Philipsburg
5 out of 5 average rating, 35 reviews

Stunning Panoramic Views Of The Ocean & St Barth!

“Villa Senorita” is located in the private residential and secured Mandara Residences. This brand new modern condominium features 164sqm/1766 sqft of interior and exterior space with WIFI throughout. The Condo consists of two master bedrooms with two bathrooms, living room with kitchen area, exterior terrace, and laundry area. All two bedrooms, the living room have unobstructed and breathtaking views of the ocean, Guana Bay Beach, Saint Barthélémy and the beautiful island nature.

Top guest favorite
A serene coastal view is captured, showcasing the shimmering blue ocean under a clear sky. Lush greenery and well-maintained gardens are visible in the foreground, while white buildings with decorative elements rest subtly along the coastline.
Home in Cole Bay
4.95 out of 5 average rating, 20 reviews

Blue Palm Estate Townhouse w/ Ocean View

Welcome to Blue Palm Estate! Sint Maarten/Saint Martin is a very small island owned by the Netherlands and France. This 2 bedroom 3 bathroom is located in Pelican Key. It is a beautiful, safe and private area in a gated 4 unit villa. It is walking distance to many restaurants on the main street which is a very popular area with tons of delicious restaurants and wonderful shops to peruse. You will also see a beautiful sandy beach within 5 minute walking distance to the unit!

Top guest favorite
Steps leading down to a sandy beach are framed by a white railing. The clear turquoise water laps gently at the shore, revealing a mix of sand and smooth stones. Bright sunlight illuminates the tranquil scene, highlighting the serene coastal atmosphere.
Home in Cole Bay
5 out of 5 average rating, 41 reviews

Pelican key - BEACH FRONT Villa

Stunning beachfront villa of 200 sqm, 6 steps away to the beach with private pool! It features 3 spacious, AC bedrooms, each with a smart TV and bathroom. Large living room opens onto the Caribbean Sea, whith fully equipped kitchen, dining area that seats 8 and a bar area to enjoy. The terrace is for outdoor living, with bbq, shaded dining area comfortable sofas and sun loungers directly to the beach & swimming pool.

Guest favorite
Home in saint-martin
4.91 out of 5 average rating, 67 reviews

Slowlife! Blooming Villa! Freshly Renovated

Located in Terres Basses, near Baie Rouge beach, and with a magnificent view of the ocean, you will find a fully private 2 bedrooms, 2 bathrooms villa, ideal place for a family, couples or friends. With a large covered terrace, a pretty salt water swimming pool in the middle of a deck, all in the heart of a tropical garden, where you will definitely enjoy the wonderful ocean view that will allow you to relax.

Top guest favorite
A shaded outdoor seating area features a comfortable sectional sofa and a natural wood coffee table. Tropical palm trees and a view of the pool enhance the space, while loungers are positioned nearby. Soft textiles in muted colors contribute to a laid-back ambiance.
Home in SAINT MARTIN
5 out of 5 average rating, 30 reviews

The best view on the island!

Casa Victoire is fully equipped with everything you might need for a comfortable and relaxing stay! Enjoy relaxing moments while taking in the view from your private terrace or relaxing in the heated pool while enjoying stunning ocean views. Canoes and kayaks are available for an unforgettable experience in the Cul de Sac Bay Nature Reserve Looking forward to hosting you at La Casa Victoire!

Superhost
An inviting infinity pool stretches toward the horizon, offering uninterrupted views of the ocean and coastline. A covered terrace with two lounge chairs is positioned nearby, framed by a modern architectural structure that enhances the surrounding scenic beauty.
Home in Indigo Bay
4.84 out of 5 average rating, 210 reviews

Préstige - Luxurious 3 bedroom by the Beach

Nestled on the hills of Indigo Bay, Préstige is located midway between Philipsburg and the Simpson Bay touristic hangout. Préstige exudes relaxation the minute you walk through the door, elegant and distinguished! The 3-bedroom spacious residence sleeps six! Overlooking Indigo Beach with private swimming pool! Caribbean living, yours to enjoy!

Top guest favorite
Home in Indigo Bay
4.93 out of 5 average rating, 15 reviews

Fleur De Lis, Private POOL, 2 bed. 2 bath

Kick back and relax in this calm, stylish space, with your own private pool. Both bedrooms and living room have ocean views. Located in Indigo Bay that is central to all the restaurants, market and walking distance to the beach and Indigo Bay Beach Club and restaurant.

Superhost
A bright living area features a spacious sofa with light-colored pillows, positioned opposite a wall-mounted television. Two circular coffee tables are placed on a natural fiber rug. A modern lamp and wooden chair add texture, while indoor plants bring a touch of greenery.
Home in Cole Bay
4.91 out of 5 average rating, 34 reviews

Designer 3BR House w Pool, Sunsets & Ocean Views

Designer 3 bedroom home in Pelican Key. Pelican Key is the best location in Sint Maarten on a hill above Simpson Bay. Walk to restaurants, bars, and beaches. Spend time by the large communal pool and garden. And sunsets every day from the terrace!

Popular amenities for Simpson Bay house rentals

When is the best time to visit Simpson Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$62,566 GYDG$48,755 GYDG$57,544 GYDG$57,125 GYDG$56,916 GYDG$41,850 GYDG$61,938 GYDG$62,147 GYDG$26,156 GYDG$41,850 GYDG$41,850 GYDG$57,544 GYD
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