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House holiday 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 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
5 out of 5 average rating, 34 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.

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
4.81 out of 5 average rating, 21 reviews

Townhouse Villa LX

Superbe Maison mitoyenne, faisant partie d’une petite copropriété sécurisée dans le quartier de Beacon Hill. Située à 5 minutes de l’aéroport, vous pourrez admirer le ballet unique des avions au dessus de la plage de Maho, sans nuisances sonores, depuis la piscine partagée installée sur un rooftop. Très spacieuse avec ses 3 belles chambres, 2 salles de bain, entièrement climatisée, terrasse arborée et cuisine équipée. Située à proximité des restaurants et clubs. Accès plage direct en 1 minute.

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, 96 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
The pool area is surrounded by lush palm trees and vibrant tropical landscaping. A spacious swimming pool reflects the clear blue sky, while lounge chairs sit invitingly on the deck. The architecture of the surrounding buildings features white walls and red-tiled roofs.
Home in Simpson Bay
5 out of 5 average rating, 15 reviews

Sbyc 3bdr with private jacuzzi and 3 shared pools

This beautiful 3 bed - 3,5 bath luxurious corner unit in Simpson Bay Yacht club (SBYC) is located in the best spot of the island. 2 bedrooms have King beds and the third has a Full size bed. We can also add a crib. Check the pictures of our private rooftop terrace with Jacuzzi. 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 3 bdr house if you want to enjoy all of SXM.

Guest favourite
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, 70 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 favourite
Home in Lowlands
4.95 out of 5 average rating, 22 reviews

Soleil & Sage Haven,2BR 2.5BH Townhouse in Cupecoy

Located in one of SXM's upscale neighborhoods, Cupecoy, this rental is an absolute treat for any vacationer! Having two of the most beautiful beaches on the island, Mullet Bay & Cupecoy Beach few minutes away, excellent location for snorkeling. Private Plunge Pool, Rooftop Terrace & Bbq grill for personal use. This amazing town house is also located within a short distance of the popular Maho Beach where you can watch the planes land over the beach. It is truly a vacationer's paradise!

Top guest favourite
Home in Philipsburg
5 out of 5 average rating, 32 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 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 favourite
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, 27 reviews

La plus belle vue de l'ile !

La Casa Victoire est entièrement équipée avec tout ce dont vous pourriez avoir besoin pour un séjour confortable et relaxant ! Profitez de moments de détente en admirant la vue depuis votre terrasse privée ou en vous relaxant dans la piscine chauffée en profitant de la vue imprenable sur l'océan. Canoés et kayak sont à votre disposition pour une expérience inoubliable dans la réserve naturel de la baie de Cul de Sac Au plaisir de vous accueillir à La Casa Victoire !

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
4.78 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!

Top guest favourite
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, 39 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.

Luxe
Home in Les Terres Basses
4.94 out of 5 average rating, 49 reviews

CoCo Signature Luxurious Villa & Exceptional View

Renovated in 2022 and located in Terres Basses (French side), Villa CoCo Signature features 4 spacious bedrooms and offers breathtaking 180˚ views of the lagoon and the island of Saint-Martin. The warm Mediterranean-style ambiance and the outdoor kitchen the opens onto a private infinity-pool are perfect for enjoying the stunning scenery while relaxing, swimming or cooking.

Popular amenities for house rentals in Simpson Bay

When is the best time to visit Simpson Bay?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$384 SGD$299 SGD$353 SGD$350 SGD$349 SGD$257 SGD$380 SGD$381 SGD$160 SGD$257 SGD$257 SGD$353 SGD
Avg. temp26°C26°C26°C27°C28°C29°C29°C29°C29°C29°C28°C27°C

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 $77 SGD per night before taxes and fees

  • Verified guest reviews

    Over 710 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    10 properties feature pools

  • Wifi availability

    20 of Simpson Bay holiday rentals include wifi 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!