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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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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, 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.

Guest favourite
An outdoor terrace features a wooden deck, complemented by various potted plants. A glass table is surrounded by light-colored chairs. In the background, a sparkling blue pool is visible, alongside a lush green area and a view of the coastline and sky.
Home in Les Terres Basses
5 out of 5 average rating, 12 reviews

Modern Bungalow with Stunning Seaview & Pool

Découvrez notre Luxueux & Cosy Bungalow Kombawa, chambre séparée, cuisine tout équipée, canapé lit à disposition dans le salon, grand placard, douche à l'italienne, idéal à 2 ou 3, ou en famille. Il est situé à quelques minutes à pied de la très belle plage de Baie aux Prunes, la vue époustouflante vous permettra d'admirer les couchers de soleil sur la mer. Venez vous ressourcer au coeur de cet écrin de verdure à la douce mélodie du chant des oiseaux idéalement situé entre les 2 parties de l'île

Guest favourite
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
4.88 out of 5 average rating, 16 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.

Top Guest favourite
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, 50 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 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
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 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
4.97 out of 5 average rating, 58 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.

Guest favourite
A modern villa exterior features a sleek infinity pool surrounded by a tiled terrace. A spacious dining area is set beneath a pergola, complemented by tropical plants and a distant hillside view. Sunlight reflects off the pool's surface, enhancing the inviting atmosphere.
Home in Sint Maarten
5 out of 5 average rating, 23 reviews

Infinite Blue – Elegant Villa & Turquoise Views

Infinite Blue is an elegant 3-bedroom, comfortable villa with the perfect relaxing atmosphere. The kitchen is fully equipped, and all social areas are comfortable spaces, with a nice design and excellent ocean views. The terrace area has a spacious dining room (area), Inf. pool, outside BBQ, outside shower, and a jacuzzi 36 C degrees depending on the weather, from 6pm until 12 am. For couples or families. The community location is great and safe! It is close to the main sites of interest.

Guest favourite
Home in Lowlands
5 out of 5 average rating, 6 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!

Guest favourite
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 favourite
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, 33 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!

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, 194 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, 29 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.

Popular amenities for Simpson Bay house rentals

When is the best time to visit Simpson Bay?

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Avg. price$536 NZD$513 NZD$491 NZD$451 NZD$450 NZD$331 NZD$489 NZD$491 NZD$207 NZD$331 NZD$331 NZD$455 NZD
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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 $66 NZD per night before taxes and fees

  • Verified guest reviews

    Over 610 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, Wi-Fi and Pool across Simpson Bay rentals

  • 4.9 Average rating

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