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House holiday rentals in Simpson Bay

Find and book unique houses on Airbnb

Quick stats about house rentals in Simpson Bay

  • Total holiday rentals

    Explore 20 holiday rentals in Simpson Bay

  • Nightly prices starting at

    Simpson Bay holiday rentals start at $97 AUD per night before taxes and fees

  • Verified guest reviews

    Over 620 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Holiday rentals with a pool

    10 properties feature pools

  • Wi-Fi availability

    20 of Simpson Bay holiday rentals include Wi-Fi 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!

Top-rated house rentals in Simpson Bay

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

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Guest favourite
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 Koolbaai
4.87 out of 5 average rating, 47 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.

Guest favourite
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
4.98 out of 5 average rating, 44 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.

Top Guest favourite
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, 106 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!

Guest favourite
An expansive infinity pool extends toward scenic ocean views, framed by gentle hills. Several lounge chairs line the pool area, inviting relaxation. The tranquil bay is dotted with boats, while the horizon features a backdrop of distant islands under a partly cloudy sky.
Home in Pelican
5.0 out of 5 average rating, 18 reviews

Luxurious villa with magnificent view ALSO 6bedr!

This gorgeous 4 bedroom - 4 bath villa is the best place to stay for your next vacation. The villa is also available as 6 bedroom. please reach out to us. The views are the best on the island as you will be overlooking Simpson Bay, the airport, the lagoon, the bridge and of course Anguilla. You are minutes away from restaurants, bars, shops and activities. This luxurious villa with teak furniture inside and outside has a beautiful pool with stunning ocean views and sleeps up to 8 people.

Top Guest favourite
Home in Philipsburg
5.0 out of 5 average rating, 42 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 favourite
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 Koolbaai
4.95 out of 5 average rating, 22 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!

Guest favourite
A spacious verandah features a comfortable seating area with a light-colored couch and a dark wicker coffee table. Lush greenery is displayed in a yellow planter, with panoramic views of the hills and bright blue sky in the background.
Home in Indigo Bay
4.79 out of 5 average rating, 218 reviews

La Pearle - Luxurious 1 Bedroom Condo By the Beach

Nestled on the hills of Indigo Bay, La Pearle is located midway between Philipsburg and the Simpson Bay touristic hang out. La Pearle exudes relaxation the minute you walk through the door! Awake to watching the Allure of the Seas make its way into the harbor. La Pearle, elegant, sophisticated and distinguished! The 1- bedroom spacious condo sleeps two! Experience luxury with a huge verandah overlooking the Indigo beach, Caribbean living, yours to enjoy!

Guest favourite
A tranquil pool reflects the azure sky and distant boats. Surrounded by lush greenery, the pool area features a cascading waterfall and is bordered by smooth stones. A wooden partition provides privacy, enhancing the serene atmosphere of the waterfront retreat.
Home
4.89 out of 5 average rating, 100 reviews

ALMOND BLUE ...Pinel bay view - caribbean feeling

Relax in the Caribbean in this beautiful house with its extraordinary view of Pinel Bay, voted the 3rd most beautiful destination in the Caribbean. In the middle of a nature reserve overlooking St Barthélémy, you will swim with turtles and exotic fish. With access to the sea below the house, you can enjoy the kayaks available to go and enjoy a lobster or cocktail in one of the 2 restaurants on Pinel Island. St Martin – The Pearl of the Caribbean!

Superhost
A panoramic view of the turquoise sea is captured from the rooftop, with the coastline and palm trees visible in the foreground. Soft white clouds drift over the lush green mountains in the distance, creating a serene backdrop to the vibrant scene.
Home in Simpson Bay
4.8 out of 5 average rating, 25 reviews

Townhouse Villa LX

Beautiful townhouse, part of a small secure condominium in the Beacon Hill neighborhood. Located 5 minutes from the airport, you can admire the unique ballet of planes over Maho Beach, without noise pollution, from the shared rooftop pool. Very spacious with 3 beautiful bedrooms, 2 bathrooms, fully air-conditioned, wooded terrace and equipped kitchen. Located close to restaurants and clubs. Direct beach access in 1 minute.

Guest favourite
Home in Saint Martin
4.91 out of 5 average rating, 70 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.

Superhost
Home in Lowlands
5.0 out of 5 average rating, 4 reviews

Villa Calma – Lagoon view, pool & tranquillity

Villa Calma is a spacious, fully air-conditioned 3-bedroom, 3-bathroom villa offering stunning lagoon views, a private pool, multiple terraces and a private jetty with a boat lift. Ideally located in the ultra-secure and very quiet area of Point Pirouette, right near Maho and the airport, this villa captivates with its beautiful open spaces and abundant natural light.

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
4.83 out of 5 average rating, 215 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!

Popular amenities for Simpson Bay house rentals

When is the best time to visit Simpson Bay?

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Avg. price$416 AUD$324 AUD$382 AUD$382 AUD$417 AUD$542 AUD$411 AUD$413 AUD$174 AUD$278 AUD$278 AUD$382 AUD
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