
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.

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

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.

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.

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.

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.

“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!

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!

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
House rentals with a pool

Fantastic 2 bedroom villa, swimming pools, tennis

Welcome to a slice of paradise!

Comfort & Views - LUX Fortress

Villa close to the beach

ALMOND BLUE ...Pinel bay view - caribbean feeling

Luxurious Villa "Sea La Vie"

Kanoa - 3 bedroom Remote Luxe Escape

Ocean view villa at Dawn beach
Weekly house rentals

Villa Paradis - The best views of the island!

Spacious 3 Bedroom 2 Bathroom Marigot Home

Villa Kailani 4 bedroom with Stunning Ocean Views

Aquabloom townhouse, 2BR 2.5 BH in Cupecoy

Modern 3BR AC - Views of Philipsburg & Cruise Port

3-Bedroom Home In Philipsburg, Near the Beach

BeachComber Nest | 2BR Near Maho Beach & Airport

LODGE Elegant Cocoon, Tropical Terrace, Sea View
Private house rentals

Fleur De Lis, Private POOL, 2 bed. 2 bath

Villa Prospère

Villa Incognito on the Beach

Bahia - Villa 2

Luxury Villa "Villamour" w/ Private Pool

Villa Myles Maho Beacon Hill

Stunning Panoramic Views Of The Ocean & St Barth!

Green, beaches nearby
When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £243 | £232 | £222 | £204 | £204 | £150 | £222 | £222 | £94 | £150 | £150 | £206 |
| Avg. temp | 26°C | 26°C | 26°C | 27°C | 28°C | 29°C | 29°C | 29°C | 29°C | 29°C | 28°C | 27°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!
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