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House vacation rentals in Simpson Bay

Find and book unique houses on Airbnb

Top-rated house rentals in Simpson Bay

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

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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, 20 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.

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

Sunset 2BR 2BH House in Cupecoy with Private Pool

This Brand New Luxurious town house is perfectly located in the sought after area of Cupecoy. Offering a perfect blend of comfort, convenience & Caribbean charm for a memorable stay that fits perfectly to your weekend getaways, staycation, or work from home This house will bring your Caribbean dream vacation come true. It is walking distance to the Cupecoy beach and just 5 minutes drive from MulletBay & Maho Beach It has a private plunge pool and a rooftop terrace with amazing lagoon views.

Top guest favorite
A private pool sits on a spacious wooden deck, surrounded by lush greenery. Lounge chairs are positioned nearby, offering a place to relax. The serene view encompasses a calm body of water and distant islands under a clear blue sky.
Home in Orient Bay
4.91 out of 5 average rating, 68 reviews

Paradise View, Creole house with private pool

Spacious independant house with private swimming pool 5 min walk from Orient Bay. Magnificent view on the surrounding beaches and islands. Softness of the Caribbean breeze. Lots of space with a large 600 sq ft deck to relax facing the sea. Kitchen and dining room of 250 sq ft open very widely onto the terrace. Large conditioned & ventilated living room of 350 sq ft with large sofa bed and bathroom. Upstairs, large, very bright conditioned bedroom of 350 sq ft with its office space and bathroom.

Top guest favorite
An outdoor dining area is set for a meal with an expansive table that accommodates eight or more guests. The space features sleek chairs and offers unobstructed views of the ocean and horizon, framed by clear skies. The surrounding area reflects a serene coastal ambiance.
Home in Sint Maarten
5 out of 5 average rating, 52 reviews

Ocean View Villa-Indigo Bay W/Private Pool/0 Steps

Welcome to paradise in Indigo Bay, St. Maarten! Our brand new property offers ultimate indoor-outdoor living with sliders opening to breathtaking sea views. Open-concept layout, fully-equipped kitchen, private pool and courtyard, NO STEPS, and three ocean-view bedrooms. Experience luxury and comfort at our oceanfront villa. Book now for an unforgettable vacation! *There is construction of a new hotel in the bay. Noise has been minimal but is subject to change. Contact us with any questions!*

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
5 out of 5 average rating, 82 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 favorite
An outdoor lounge area features a modern pergola with plush seating and neatly arranged towels. The infinity pool, with its seamless edge, reflects the vibrant blue of the ocean under a clear sky, providing expansive views of the coastline and surrounding landscape.
Home in Upper Prince's Quarter
4.97 out of 5 average rating, 59 reviews

Teresa’s Ocean Paradise

St. Maarten’s best kept secret with breathtaking ocean views from every room! Step into Teresa’s Ocean Paradise where you’ll wake up to panoramic views of turquoise water. Nestled in a private gated community with a communal pool overlooking the ocean, fully equipped kitchen, and two king bedrooms – each with private bathrooms. Perfectly located to enjoy the best of the Dutch and French side’s beaches and restaurants. A one-of-a-kind property to make your vacation an unforgettable retreat.

Top guest favorite
A refreshing pool area is surrounded by palm trees and colorful tropical plants. Lounge chairs are positioned near the pool, offering views of the turquoise Caribbean Sea and nearby coastline. Natural light illuminates the space, emphasizing the vibrant outdoor environment.
Home in Philipsburg
5 out of 5 average rating, 29 reviews

2 Bedroom Ocean Front Villa, Private Infinity Pool

Clearwater is a cliffside waterfront property with one of the most spectacular views on the island! Overlooking Great Bay, Philipsburg, Divi Little Bay, the turquoise Caribbean Sea and the magnificent cruise ships, this one-of-its-kind location will be sure to Wow you. It is perfectly situated for easy access to all SXM has to offer; 2 nearby beaches, restaurants, grocery stores, downtown shopping, bars and entertainment. If you are interested, checkout the 3 Bedroom option here on Airbnb.

Guest favorite
The open-concept kitchen features a central island with modern appliances and ample storage. A cozy seating area is positioned nearby, with natural light flowing in from large sliding doors leading to a furnished terrace, creating a seamless connection between indoor and outdoor spaces.
Home in SAINT MARTIN
5 out of 5 average rating, 9 reviews

2 bedroom villa on the beach!

Here begins paradise on the beach of Nettlé Bay, by the Caribbean Sea in the highly sought-after residence Nettlé Bay Beach Club with swimming pools, tennis courts. The duplex villa with sea view "Chez Tonton Zé" is a wonderful accommodation, renovated and very nicely decorated. Two beautiful king size suites, each with its own bathroom, two toilets, a very nice equipped kitchen, a spacious terrace on the sand. "Chez Tonton Zé" will be your favorite destination for your next vacation!

Guest favorite
A spacious outdoor dining area features a modern table and chairs, with a view of the beach and palm trees. The clear sky and distant mountains create a serene backdrop. Sunlight reflects off the table, adding to the inviting setting.
Home in Collectivité de Saint-Martin
4.87 out of 5 average rating, 53 reviews

"Salty Beach" - Amazing 1 bedroom beachfront

Nouveau, entièrement rénové! “Salty Beach” c’est l’idéal pour des vacances les pieds dans le sable. Situé dans la jolie résidence du Nettle Bay Beach Club sur la plage, face à la mer des Caraïbes avec une vue sublime sur les montagnes de Pic Paradis.“Salty Beach” saura vous séduire pour que vous passiez des vacances inoubliables. La résidence possède 4 piscines et 2 courts de tennis. À proximité immédiate vous trouverez une supérette, une boulangerie, des restaurants, pharmacie etc

Guest favorite
A well-lit bedroom features a spacious bed with crisp white linens and various decorative pillows. Matching bedside tables hold stylish lamps. A wall-mounted television is positioned in front of the bed, while light streaming through partially opened shutters adds a bright touch to the room.
Home in Simpson Bay
4.97 out of 5 average rating, 34 reviews

The beachcomber

Welcome to your perfect island retreat! Located in the heart of Beacon Hill, this cozy unit offers the ideal home base for exploring all that Sint Maarten has to offer. Just steps away from the island’s top attractions, you'll be within walking distance to: Maho Beach, Casinos,Restaurants & Bars. This unit is perfect for couples or solo travelers. Don’t miss out on the best location on the island – book your stay in Beacon Hill today and live like a local just steps from the action!

Top guest favorite
A shaded terrace is surrounded by lush greenery, featuring a comfortable seating area with light-colored chairs and a low table. Natural light filters through the leaves, creating a serene and inviting space for relaxation.
Home in Cul-de-Sac
4.92 out of 5 average rating, 48 reviews

LODGE Elegant Cocoon, Tropical Terrace, Sea View

Welcome to the LODGE, a unique, bright and refined style accommodation, nestled in a green setting in Cul-de-Sac, with stunning views of Îlet Pinel, Saint-Barth and the Caribbean Sea. A real cocoon for two, ideal for a romantic stay or a quiet getaway: * Terrace with panoramic view * Bright living room with TV and air conditioning * Fully equipped open kitchen * Large bedroom * Shaded terrace with dining area and outdoor lounge * Small private pool (2x2)

Guest favorite
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
4.78 out of 5 average rating, 195 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!

Popular amenities for Simpson Bay house rentals

When is the best time to visit Simpson Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ1,190ﺩ.ﺇ1,138ﺩ.ﺇ1,091ﺩ.ﺇ1,003ﺩ.ﺇ999ﺩ.ﺇ735ﺩ.ﺇ1,087ﺩ.ﺇ1,091ﺩ.ﺇ459ﺩ.ﺇ735ﺩ.ﺇ735ﺩ.ﺇ1,010
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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 ﺩ.ﺇ147 per night before taxes and fees

  • Verified guest reviews

    Over 610 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

  • 4.9 Average rating

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