
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 $89 SGD 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 & 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!
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!
4.99 out of 5 average rating, 107 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.
4.88 out of 5 average rating, 48 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!*
4.99 out of 5 average rating, 75 reviews
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.
5.0 out of 5 average rating, 19 reviews
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!
4.96 out of 5 average rating, 23 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!
4.79 out of 5 average rating, 220 reviews
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!
4.89 out of 5 average rating, 100 reviews
Sweet Home on the Beach rdc
EVENTS Exceptional. View of the bay of Marigot Feet in the water Facing the Caribbean Sea Stunning white sand beach, coconut trees, turquoise sea HIGHLIGHTS House on the beach Ideal location to visit 4 Pools 1 tennis A beautiful garden 24/7 secure residence Free parking Next door: supermarket, bakery, restaurants Great for couples GOOD TO KNOW 2 kms from Marigot Rental car recommended Wifi, cleaning fee, towels, sheets included in the price.
5.0 out of 5 average rating, 8 reviews
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.
4.81 out of 5 average rating, 26 reviews
CoCo Signature Luxurious Villa & Exceptional View
Renovated in 2022 and located in Terres Basses (French side), Villa CoCo Signature features 4 spacious bedrooms and offers breathtaking 180˚ views of the lagoon and the island of Saint-Martin. The warm Mediterranean-style ambiance and the outdoor kitchen the opens onto a private infinity-pool are perfect for enjoying the stunning scenery while relaxing, swimming or cooking.
4.95 out of 5 average rating, 62 reviews
3BR Townhouse in Pelican Key
Escape to your family's perfect Sint Maarten retreat! This bright 3-bedroom, 2.5-bath townhouse in Pelican Key comfortably hosts 8 with king beds & a fun bunk room. Enjoy a modern kitchen, two private balconies, and a shared pool just steps away. With beach access, parking, and nightlife nearby, it's the ideal home base for your unforgettable Caribbean adventure!
4.79 out of 5 average rating, 39 reviews
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!
4.83 out of 5 average rating, 215 reviewsPopular amenities for house rentals in Simpson Bay
House rentals with a pool

Sunrise Over St. Barths
4.98 out of 5 average rating, 46 reviews
3 Bed 3 Bath Villa | Private Pool | Pelican | SXM
4.83 out of 5 average rating, 23 reviews
SeaRenity Villa With Private Pool Indigo Bay
4.97 out of 5 average rating, 37 reviews
Villa Josefa SXM · Ocean View Above Friar’s Bay
5.0 out of 5 average rating, 29 reviews
Villa ELIOS 2BR SeaView
5.0 out of 5 average rating, 6 reviews
Slowlife! Blooming Villa! Freshly Renovated
4.92 out of 5 average rating, 72 reviews
Fun times ahead! Devine in You Cupecoy is calling.
4.9 out of 5 average rating, 60 reviews
Teresa’s Ocean Paradise
4.96 out of 5 average rating, 77 reviewsWeekly house rentals

Villa Kansha | 3BR Wellness Escape & Hot Tub
4.94 out of 5 average rating, 17 reviews
Macassi Beach Paradise, villa 3 chambres
5.0 out of 5 average rating, 14 reviews
Villa Amber - Spectacular Sea View - Terres Basses
5.0 out of 5 average rating, 5 reviews
Atypik Villa
4.97 out of 5 average rating, 37 reviews
New "The Beach House"
4.91 out of 5 average rating, 11 reviews
3-Bedroom Home In Philipsburg, Near the Beach
4.93 out of 5 average rating, 85 reviews
ALOHA penthouse
4.85 out of 5 average rating, 74 reviews
Villa Louisiana, Orient Bay
4.93 out of 5 average rating, 40 reviewsPrivate house rentals

Luxurious bungalow with private pool
4.96 out of 5 average rating, 85 reviews
Villa.lalabay Mont Vernon 3, Saint-Martin
4.81 out of 5 average rating, 16 reviews
Upscale Villa Hideaway in Orient Bay
4.93 out of 5 average rating, 28 reviews
2 Bedroom Ocean Front Villa, Private Infinity Pool
5.0 out of 5 average rating, 32 reviews
Prestigious Villa with Breathtaking Ocean View
5.0 out of 5 average rating, 22 reviews
Coconut Villa, Sea View, Pool, 6 People
4.92 out of 5 average rating, 12 reviews
Villa Tamarind | Luxury | Spectacular Views | 4BDR
4.96 out of 5 average rating, 83 reviews
Villa Cataleya with Jacuzzi & Pool in Orient Bay
5.0 out of 5 average rating, 9 reviewsWhen is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $382 SGD | $297 SGD | $351 SGD | $351 SGD | $383 SGD | $498 SGD | $378 SGD | $379 SGD | $159 SGD | $255 SGD | $255 SGD | $351 SGD |
| 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 apartment rentals Simpson Bay
- Rentals with pools Simpson Bay
- Pet-friendly rentals Simpson Bay
- Flat rentals Simpson Bay
- Rentals with a hot tub Simpson Bay
- Apartment rentals Simpson Bay
- Waterfront rentals Simpson Bay
- Serviced apartment rentals Simpson Bay
- Villa rentals Simpson Bay
- Beachfront rentals Simpson Bay
- House rentals Sint Maarten





