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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 $100 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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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, 40 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
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 Cole Bay
4.85 out of 5 average rating, 41 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.

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
4.78 out of 5 average rating, 23 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
A spacious outdoor terrace features a stunning infinity pool overlooking the sea, complemented by comfortable sun loungers. A shaded dining area with a stylish table set for gatherings is visible, showcasing panoramic views of the coastline and vibrant blue ocean.
Home in Upper Prince's Quarter
4.96 out of 5 average rating, 24 reviews

Vue époustouflante sur St Barth - 8 personnes

🛏️ Lit King Size 🌊 Incroyable vue panoramique sur la mer 🏊 Piscine chauffée 💧 Citerne et groupe électrogène pour un confort garanti en toute circonstance ❄️ entièrement climatisée 🛰️ Internet Starlink 🚗 Parking privé ⚡ 110V et 220V 🔐 Résidence sécurisée avec portail d'accès 🔥 Barbecue à gaz 🧹 Housekeeping offert pour les séjours de 6 nuits et plus 📺 TV internationales 🛁 Chambres et salles de bain avec vue mer 🌿 Aucun vis-à-vis pour une intimité totale 🏡 Construction neuve 2025

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, 21 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, 31 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
4.79 out of 5 average rating, 215 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
A private pool is framed by timber decking, with two wooden lounge chairs featuring light blue cushions positioned nearby. Tropical plants and palm trees surround the area, contrasting against a bright blue sky scattered with fluffy white clouds, while distant views of the sea are visible.
Home in Cul-de-Sac
4.94 out of 5 average rating, 34 reviews

Villa Pandora

Charmante Maison avec Vue sur Mer et Piscine à Cul-de-Sac pour 4 Personnes Bienvenue dans notre grande maison de deux chambres située dans le quartier de Cul-de-Sac à proximité de l’ile Pinel et à quelques minutes de Anse Marcel, la plage de Orient Bay ou de Grand Case sur la partie française de l'île. Idéale pour des vacances reposantes, notre maison offre tout le confort nécessaire pour un séjour inoubliable.

Guest favourite
Home in saint-martin
4.91 out of 5 average rating, 68 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.

Guest favourite
The living area features modern furnishings, including a light gray sofa and an accent chair. A round wooden coffee table sits on a soft area rug. A unique light fixture adds a touch of style against the dark blue accent wall, while a plant brings a hint of nature.
Home in Cole Bay
4.94 out of 5 average rating, 79 reviews

Modern 3BR with Private Pool

Escape to this modern 3-bedroom, 2.5 bath retreat with own private pool on a tropical island paradise. Each bedroom features comfortable beds and quality linens. The open-concept living area includes a fully equipped kitchen, comfortable living room, and dining area. Just a short drive from the beach, restaurants, and shops. Special long term rates available. Just send an inquiry to discuss further!

Superhost
An outdoor terrace displays a dining table surrounded by four wicker chairs, with a view overlooking the water and mountains. A pool with a tiled border sits adjacent, reflecting the sky and landscape. Ceiling panels allow natural light to illuminate the space.
Home in Cole Bay
5 out of 5 average rating, 3 reviews

Bahia - Villa 1

The Bahia Villas are located in the heart of Simpson Bay. If you're looking to have you're own private villa but want to be on walking distance to our beautiful beaches and bars and restaurants this is just the place to stay. With 3 bedrooms and 2.5 bath you can either share the villa with family or friends up to 6 guests per Villa. Or decide to have a romantic getaway.

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, 211 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$427 AUD$333 AUD$393 AUD$390 AUD$389 AUD$286 AUD$423 AUD$424 AUD$179 AUD$286 AUD$286 AUD$393 AUD
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