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House vacation rentals in Simpson Bay

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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, 36 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
Home in Lowlands
4.9 out of 5 average rating, 20 reviews

Casa Rish-2BR 2.5BH TownHouse with pool in Cupecoy

This brand new gorgeous town house is located in the sought-after area of Cupecoy. Offering a perfect blend of comfort, convenience & Caribbean charm for a memorable stay. This house will bring your Caribbean dream vacation come true. It is walking distance to the Cupecoy beach. It has a private plunge pool and a rooftop terrace with great lagoon views. It is a Combination of charming and contemporary that fits perfectly to your weekend getaways, staycation, business trip or work from home.

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, 97 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!

Top 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
4.96 out of 5 average rating, 71 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.

Superhost
The outdoor area features a large swimming pool, surrounded by lounge chairs and tropical plants. A table is set with colorful cups and striped accessories, contributing to a relaxed ambiance. The villa can be seen in the background, offering a serene and inviting space.
Home in SAINT MARTIN
5 out of 5 average rating, 6 reviews

La Villa du Lagon : cosy villa for 8 people

Ravissante villa située à la baie Nettlé, parfait pour un séjour en famille ou entre amis. Chaque pièce de cette maison a été décorée avec des meubles et des éléments de décoration de très haute qualité, créant une ambiance luxueuse et chaleureuse. Quatre belles chambres, un salon spacieux, une belle cuisine très bien équipée, une belle terrasse couverte et non couverte, une piscine et un jacuzzi : tout est prévu pour que vous passiez un séjour inoubliable dans notre "Friendly Island".

Top guest favorite
Home in Philipsburg
5 out of 5 average rating, 33 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!

Guest favorite
An inviting living area showcases comfortable seating with soft cushions arranged around a glass coffee table. A clean, open layout leads to a dining space in the background, while elegant wooden stairs ascend to the upper level, accented by decorative wall plates.
Home in Upper Prince's Quarter
4.94 out of 5 average rating, 68 reviews

Caribbean Style Family Home

This lovely dwelling is a Caribbean style home with a modern tropical twist; Ideal for groups/families looking for real Caribbean experience. located in a quiet residential area (+valley view) with a private enclosed yard, parking and backyard with home grown organic herbs for natural teas. Come and live like a local among the locals: A 7 minute drive to our beautiful boardwalk beach in Philipsburg and its duty free shops. 7-10 mins to the famous orient beach.

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, 211 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 favorite
Home in Simpson Bay
5 out of 5 average rating, 9 reviews

Simpson Bay Yacht Club condo

This beautiful 2 bed - 2 bath luxurious condo in Simpson Bay Yacht club (SBYC) is located in the best spot of the island. 2 bedrooms with king size beds, we can also add a crib. SBYC has 3 pools and 2 tennis courts for you to use. The Beach is at 5 min walking and so are supermarkets, restaurants, bakeries, bars, casinos etc. This is the perfect 2bdr house if you want to enjoy all of SXM. This condo has everything you need.

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, 208 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!

Superhost
Home in Les Terres Basses
5 out of 5 average rating, 3 reviews

Villa Coral | Collection Villas Saint-Martin

Carefully designed, Villa Coral offers two spacious and comfortable bedrooms, perfect for two couples looking travelling as a group, or a small family. The villa's elegant pool (4.30 m x 13.32 m / 14' x 43') provides a serene space to unwind, and its length is ideal for those who enjoy a few laps in complete privacy.

Popular amenities for Simpson Bay house rentals

When is the best time to visit Simpson Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$62,532 GYDG$48,729 GYDG$57,513 GYDG$57,095 GYDG$56,886 GYDG$41,828 GYDG$61,905 GYDG$62,114 GYDG$26,142 GYDG$41,828 GYDG$41,828 GYDG$57,513 GYD
Avg. temp26°C26°C26°C27°C28°C29°C29°C29°C29°C29°C28°C27°C

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$12,548 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!