
House vacation 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.

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.

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

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.

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.

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!*

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!

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.

SeaRenity Villa With Private Pool Indigo Bay
Welcome to SeaRenity Villa, your private escape in the exclusive gated community of Indigo Bay. This modern and tastefully decorated villa offers the perfect balance of comfort, style, and Caribbean charm. Wake up to breathtaking ocean views from the airy, light-filled living spaces, and step outside to your own private pool surrounded by lush privacy. Whether you’re lounging with a book, sharing meals on the terrace, or watching the sunset over the bay, every moment here feels effortless.

Luxurious villa with magnificent view ALSO 6bedr!
This gorgeous 4 bedroom - 4 bath villa is the best place to stay for your next vacation. The villa is also available as 6 bedroom. please reach out to us. The views are the best on the island as you will be overlooking Simpson Bay, the airport, the lagoon, the bridge and of course Anguilla. You are minutes away from restaurants, bars, shops and activities. This luxurious villa with teak furniture inside and outside has a beautiful pool with stunning ocean views and sleeps up to 8 people.

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!

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!

BeachComber Nest | 2BR Near Maho Beach & Airport
This cozy 2-bedroom home in Beacon Hill is just 5 minutes from the airport and within walking distance of iconic Maho Beach and vibrant Maho Village. Ideal for travelers seeking comfort and relaxation, it’s close to shops, restaurants, pharmacies, and nightlife less than a 5-minute drive or 10-minute walk. Located in a secure, exclusive residence with nighttime security and parking.
Popular amenities for Simpson Bay house rentals
House rentals with a pool

Villa Paradis - The best views of the island!

Princess Villa with Sea View and Private Pool Anse Marcel

Villa Blue Lagoon SXM

No Name in Paradise, 2 bdr house with private pool

Beautiful villa with private swimming pool.

Prestigious Villa with Breathtaking Ocean View

LODGE Elegant Cocoon, Tropical Terrace, Sea View

3 B Large Hilltop Villa with Ocean & Pond view
Weekly house rentals

Spacious 3 Bedroom 2 Bathroom Marigot Home

Casa Bay Studio, Cole Bay

Bahia - Villa 2

Coco's Beach House - Simpson Bay Beach

Caribbean Style Family Home

3-Bedroom Home In Philipsburg, Near the Beach

Villa Allamanda a Indigo Bay

House on Orient Bay, ideally located
Private house rentals

Villa Prospère

Villa Incognito on the Beach

Peaceful Paradise

VILLA CECILIA

Sea La’Vie — 2mins walk from the beach!

Luxury Villa "Villamour" w/ Private Pool

Victoria Villa with private pool

Villa Myles Maho Beacon Hill
When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $324 | $310 | $297 | $273 | $272 | $200 | $296 | $297 | $125 | $200 | $200 | $275 |
| Avg. temp | 79°F | 79°F | 79°F | 80°F | 82°F | 84°F | 84°F | 84°F | 84°F | 83°F | 82°F | 80°F |
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 $40 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!
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