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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, 18 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
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, 10 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

Top guest favorite
Home in Lowlands
5 out of 5 average rating, 6 reviews

Casa Xanadu 1BR,1.5BH with private pool in Cupecoy

This Stunning 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. 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
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 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, 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 favorite
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.

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.

Superhost
Home in Orient Bay
5 out of 5 average rating, 3 reviews

Upscale Villa Hideaway in Orient Bay

À 70 mètres seulement de la plage mythique d'Orient Bay, cette villa haut de gamme vous ouvre ses portes pour un séjour inoubliable, entre élégance et art de vivre caribéen. Dès votre entrée, une piscine chauffée d'une longueur de 12 mètres. Les 3 suites raffinées et climatisées, chacune avec sa salle de bain, évoquent le calme, l’intimité et le confort. Les matières naturelles, les couleurs apaisantes et la literie haut de gamme créent une atmosphère propice au repos et aux doux réveils.

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, 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 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
4.77 out of 5 average rating, 191 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!

Superhost
Home in saint-martin
4.9 out of 5 average rating, 59 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.

Popular amenities for Simpson Bay house rentals

When is the best time to visit Simpson Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$67,748 GYDG$64,821 GYDG$62,103 GYDG$57,084 GYDG$56,875 GYDG$41,820 GYDG$61,894 GYDG$62,103 GYDG$26,138 GYDG$61,057 GYDG$51,439 GYDG$69,839 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$8,364 GYD 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!