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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 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
5 out of 5 average rating, 15 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
Home in Cole Bay
4.92 out of 5 average rating, 12 reviews

Villa Kansha • Tranquil 3-BDR Island Escape

Designed to restore, Kansha is a 3-bdroom, 4-bath retreat blending island warmth with minimalist calm. Just minutes from beaches, dining, & attractions, it offers a peaceful escape for rejuvenation & reconnection. Its open & spacious layout connects indoor & outdoor spaces. Meditate in the Zen Den, unwind in lush gardens, or soak in the hot tub. “Kansha”, meaning gratitude, captures the essence of this home. Here, peace isn’t something you search for; it’s something you return to with gratitude.

Top 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
4.81 out of 5 average rating, 21 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.

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
4.83 out of 5 average rating, 18 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, 53 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!*

Top 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, 86 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, 59 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
Home in Simpson Bay
4.67 out of 5 average rating, 3 reviews

Coco's Beach House - Simpson Bay Beach

Coco's Beach House is a stunning property just steps away from the Simpson bay beach. It will leave you feeling like you are in paradise, 2 King bedrooms with ensuite, full kitchen, 2 private patios, glittering glimpses of the beautiful turquoise ocean and all the comforts of home. It is the perfect spot for 2 couples or a family with small children. Situated in the heart of the Island, we are walking distance to some of the nicest restaurants on the island, bakery, restaurants & nightlife.

Guest favourite
Home in Pelican
5 out of 5 average rating, 6 reviews

4 bedroom villa + 2bedr apt (sleeps 12) in Pelican

This 4 bedroom/ 4bathroom villa with separate 2 bedroom / 2 bathroom apartment is ideal for a group or family vacation. Enjoy time together while having enough space to relax as well. On the large deck you will find the gorgeous pool with stunning views where you can enjoy dinner, drinks or lounge time. The house is located on a hill overlooking the bay, the lagoon and you can see the planes coming in and Anguilla in the distance. The apartment has a separate entrance with 2 bdr, 2 bath.

Superhost
The upper-level house is framed by palm trees and surrounded by a spacious, paved area. A staircase leads to the entrance, while multiple seating arrangements are positioned on the balcony. The blue sky and ample sunlight create a vibrant setting.
Home in Simpson Bay
4.68 out of 5 average rating, 19 reviews

“Les Medes” 3 bedroom in Beautiful Beacon Hill

Perfectly located in Beacon Hill neighborhood, this spacious 3-bedroom, upper-level house offers the ideal vacation getaway. Just a 2-minute walk to the stunning Simpson Bay Beach, where you can enjoy clear waters and laid-back vibes of D’s Beach Bar & Grill, serving delicious food, drinks, and entertainment. 10-minute walk to Maho Beach, famous for planes flying overhead, Maho Village with great restaurants, nightlife, and shopping. The perfect vacation awaits you!

Superhost
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, 199 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 spacious pool area is highlighted by a large swimming pool, surrounded by a wooden deck. A sun lounger is positioned nearby, featuring a folded towel on it. The backdrop showcases the villa's white exterior and a bright blue sky with fluffy clouds.
Home
5 out of 5 average rating, 22 reviews

Atypik Villa

Spacious 200 m² villa with panoramic views of Orient Bay Beach. It is characterized by a very large swimming pool, adjacent to a large partially shaded terrace, equipped with a comfortable outdoor lounge and an ideal table to enjoy your aperitifs and meals while admiring the sea. Facing south, it enjoys beautiful sunshine from sunrise to sunset, as well as the softness of the trade winds.

Popular amenities for house rentals in Simpson Bay

When is the best time to visit Simpson Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price£243£232£222£204£204£150£222£222£94£150£150£206
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 £30 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 & 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

  • 4.9 Average rating

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