
House vacation rentals in Simpson Bay
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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 G$12,525 GYD per night before taxes and fees

Verified guest reviews
Over 710 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

4.8 Average rating
Simpson Bay stays are highly rated by guests—averaging 4.8 out of 5!
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.

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.

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!

Villa Bahia
À quelques pas de la mer, dans un environnement paisible, la Villa Bahia, spacieuse, baignée de lumière et pensée dans un esprit chaleureux, offre une parenthèse élégante entre verdure et eau turquoise. La villa propose 3 chambres avec de larges dressings et leurs salle de bain. La cuisine, conviviale, fonctionnelle, est ouverte sur une vaste pièce de vie, vue mer et entièrement équipée. Située dans une résidence sécurisée en cours de rénovation, à proximité d’un supermarché et de restaurants.

Stunning Panoramic Views Of The Ocean & St Barth!
“Villa Senorita” is located in the private residential and secured Mandara Residences. This brand new modern condominium features 164sqm/1766 sqft of interior and exterior space with WIFI throughout. The Condo consists of two master bedrooms with two bathrooms, living room with kitchen area, exterior terrace, and laundry area. All two bedrooms, the living room have unobstructed and breathtaking views of the ocean, Guana Bay Beach, Saint Barthélémy and the beautiful island nature.

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!

New "The Beach House"
By the Caribbean Sea, come spend your next vacation with your feet in the water in this wonderful air-conditioned duplex villa, 2 bedrooms, 2 bathrooms, 2 toilets, swimming pool, tennis, parking. "La maison sur la plage" renovated, decorated, and perfectly furnished, is located in the very beautiful secure residence: Le Nettlé Bay Beach Club, within immediate walking distance of a small supermarket, 5 good restaurants, a deli, a bakery, a wine cellar, and a delicatessen.

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!

Pelican key - BEACH FRONT Villa
Stunning beachfront villa of 200 sqm, 6 steps away to the beach with private pool! It features 3 spacious, AC bedrooms, each with a smart TV and bathroom. Large living room opens onto the Caribbean Sea, whith fully equipped kitchen, dining area that seats 8 and a bar area to enjoy. The terrace is for outdoor living, with bbq, shaded dining area comfortable sofas and sun loungers directly to the beach & swimming pool.

The best view on the island!
Casa Victoire is fully equipped with everything you might need for a comfortable and relaxing stay! Enjoy relaxing moments while taking in the view from your private terrace or relaxing in the heated pool while enjoying stunning ocean views. Canoes and kayaks are available for an unforgettable experience in the Cul de Sac Bay Nature Reserve Looking forward to hosting you at La Casa Victoire!

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!

Villa Pandora
Charming House with Sea View and Pool in Cul-de-Sac for 4 People Welcome to our large two bedroom house located in the Cul-de-Sac district close to Pinel Island and a few minutes from Anse Marcel, Orient Bay or Grand Case beach on the French part of the island. Ideal for a relaxing holiday, our house offers all the comforts for a memorable stay.
Popular amenities for Simpson Bay house rentals
House rentals with a pool

Villa Paradis - The best views of the island!

Ocean View Villa-Indigo Bay W/Private Pool/0 Steps

Simpson Bay Yacht Club condo

Slowlife! Blooming Villa! Freshly Renovated

Townhouse Villa LX

SeaRenity Villa With Private Pool Indigo Bay

Prestigious Villa with Breathtaking Ocean View

2 Bedroom Ocean Front Villa, Private Infinity Pool
Weekly house rentals

Stunning Ocean View from Balcony & Pool - Sleep 10

ALOHA penthouse

ALMOND BLUE ...Pinel bay view - caribbean feeling

Luxurious Villa "Sea La Vie"

"Sweet Home on the Beach"

Villa Leones spectacular view, authentic charm

Villa Kansha | 3BR Wellness Escape & Hot Tub

Villa M: Brand-new with breathtaking ocean views
Private house rentals

Bahia - Villa 1

Villa Prospère

Casa Bay Studio, Cole Bay

Coco's Beach House - Simpson Bay Beach

Pelican Paradise

3-Bedroom Home In Philipsburg, Near the Beach

No Name in Paradise, 2 bdr house with private pool

Atypik Villa
When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$62,418 GYD | G$48,640 GYD | G$57,407 GYD | G$56,990 GYD | G$56,781 GYD | G$41,751 GYD | G$61,791 GYD | G$62,000 GYD | G$26,094 GYD | G$41,751 GYD | G$41,751 GYD | G$57,407 GYD |
| 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 |
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