
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 $122 NZD 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, Wi-Fi 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.

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!
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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.
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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.
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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!*
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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.
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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!
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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!
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ALMOND BLUE ...Pinel bay view - caribbean feeling
Relax in the Caribbean in this beautiful house with its extraordinary view of Pinel Bay, voted the 3rd most beautiful destination in the Caribbean. In the middle of a nature reserve overlooking St Barthélémy, you will swim with turtles and exotic fish. With access to the sea below the house, you can enjoy the kayaks available to go and enjoy a lobster or cocktail in one of the 2 restaurants on Pinel Island. St Martin – The Pearl of the Caribbean!
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Townhouse Villa LX
Beautiful townhouse, part of a small secure condominium in the Beacon Hill neighborhood. Located 5 minutes from the airport, you can admire the unique ballet of planes over Maho Beach, without noise pollution, from the shared rooftop pool. Very spacious with 3 beautiful bedrooms, 2 bathrooms, fully air-conditioned, wooded terrace and equipped kitchen. Located close to restaurants and clubs. Direct beach access in 1 minute.
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Villa Calma – Lagoon view, pool & tranquility
Villa Calma is a spacious, fully air-conditioned 3-bedroom, 3-bathroom villa offering breathtaking views of the lagoon, a private pool, multiple terraces, and a private dock with a boat lift. Conveniently located in the ultra-secure and very quiet area of Point Pirouette, right next to Maho and the airport, the villa is appealing thanks to its beautiful layout and abundant natural light.
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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!
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Spacious 3BR with Private Cozy Pool
This spacious 3-bedroom, 2.5-bathroom home with its own private pool is the perfect retreat for those seeking a luxurious yet cozy getaway. The home is centrally located Cole Bay. It sleeps up to 6 guests and features a private backyard, a fully equipped kitchen and a short drive to beaches, restaurants and supermarkets.
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Popular amenities for Simpson Bay house rentals
House rentals with a pool

Sweet Home on the Beach rdc
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3 Bed 3 Bath Villa | Private Pool | Pelican | SXM
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Indigo Bay Condo Shamrock 2 Bed 2 Bath Ocean Views
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Slowlife! Blooming Villa! Freshly Renovated
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Fun times ahead! Devine in You Cupecoy is calling.
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Teresa’s Ocean Paradise
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Villa ELIOS 2BR SeaView
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Villa Josefa SXM · Ocean View Above Friar’s Bay
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Weekly house rentals

3BR Townhouse in Pelican Key
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Villa Kansha | 3BR Wellness Escape & Hot Tub
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3-Bedroom Home In Philipsburg, Near the Beach
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ALOHA penthouse
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4 Bedroom Luxury Villa, Sea Views, Pelican Key
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Villa Paradis - The best views of the island!
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Luxurious bungalow with private pool
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SABLE house, sleeps 2. Sea view, private pool.
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Private house rentals

Villa Suzanna in the middle of the Orient Bay
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Prestigious Villa with Breathtaking Ocean View
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Villa Terres Basses
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Stunning Ocean View from Balcony & Pool - Sleep 10
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2 Bedroom Ocean Front Villa, Private Infinity Pool
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Upscale Villa Hideaway in Orient Bay
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Villa Areca • 3BR waterfront with kayaks, WiFi, AC
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Villa Kailani 4 bedroom with Stunning Ocean Views
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When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $523 NZD | $407 NZD | $481 NZD | $481 NZD | $525 NZD | $682 NZD | $518 NZD | $519 NZD | $219 NZD | $350 NZD | $350 NZD | $481 NZD |
| 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 |
Destinations to explore
- Family-friendly rentals Simpson Bay
- Rentals with beach access Simpson Bay
- Beach condo rentals Simpson Bay
- Rentals with pools Simpson Bay
- Pet-friendly rentals Simpson Bay
- Apartment rentals Simpson Bay
- Rentals with a hot tub Simpson Bay
- Condo rentals Simpson Bay
- Waterfront rentals Simpson Bay
- Serviced apartment rentals Simpson Bay
- Villa rentals Simpson Bay
- Beachfront rentals Simpson Bay
- House rentals Sint Maarten





