
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$14,642 GYD per night before taxes and fees

Verified guest reviews
Over 620 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!
Top-rated house rentals in Simpson Bay
Guests agree: these houses are highly rated for location, cleanliness, and more.

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.

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.

Slowlife - Villa Wellness 4 beds
Wellness Villa is a luxury vacation home, this villa will be your majestic vacation home in the Caribbean. Since the moment you step into the elegant entrance surrounded by a beautiful tropical garden. This elegant villa was designed for our guest’s greatest comfort and relaxation, located in Terres Basses with spectacular lagoon and ocean view from our large terrace with an infinity pool and a jacuzzi, just 5 minutes from the exclusive and gorgeous Long Bay, you will experience a unique holiday

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
Just a short walk from the sea, in a peaceful setting, Villa Bahia is spacious, bathed in light, and designed with a warm atmosphere, offering an elegant retreat amidst greenery and turquoise water. The villa offers 3 bedrooms with large walk-in closets and their own bathrooms. The kitchen is welcoming, functional, and opens onto a large living room; it has a sea view and is fully equipped. Located in a secure residence currently being renovated, close to a supermarket and restaurants.

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!

Breathtaking view of St Barth – 8 people
🛏️ King Size Bed 🌊 Incredible panoramic sea views 🏊 Heated pool 💧 Tank and generator for guaranteed comfort in all circumstances ❄️ Fully air conditioned 🛰️ Starlink Internet 🚗 Private parking ⚡ 110V and 220V 🔐 Secure residence with access gate 🔥 Gas barbecue 🧹 Complimentary housekeeping for stays of 6 nights or more 📺 International TV 🛁 Bedrooms and bathrooms with sea views 🌿 Not overlooked for complete privacy 🏡 New construction 2025

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.

Slowlife! Blooming Villa! Freshly Renovated
Located in Terres Basses, near Baie Rouge beach, and with a magnificent view of the ocean, you will find a fully private 2 bedrooms, 2 bathrooms villa, ideal place for a family, couples or friends. With a large covered terrace, a pretty salt water swimming pool in the middle of a deck, all in the heart of a tropical garden, where you will definitely enjoy the wonderful ocean view that will allow you to relax.

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!

Bahia - Villa 1
The Bahia Villas are located in the heart of Simpson Bay. If you're looking to have you're own private villa but want to be on walking distance to our beautiful beaches and bars and restaurants this is just the place to stay. With 3 bedrooms and 2.5 bath you can either share the villa with family or friends up to 6 guests per Villa. Or decide to have a romantic getaway.
Popular amenities for Simpson Bay house rentals
House rentals with a pool

SABLE house, sleeps 2. Sea view, private pool.

Villa Pandora

Modern 3BR with Private Pool

Teresa’s Ocean Paradise

Upscale Villa Hideaway in Orient Bay

Villa Paradis - The best views of the island!

Pelican Pearl Villa with Pool and Generator

PALM BLUE Caribbean Pinel Bay View
Weekly house rentals

Villa Kansha | 3BR Wellness Escape & Hot Tub

Villa Josefa SXM · Ocean View Above Friar’s Bay

Luxurious Villa "Sea La Vie"

"Sweet Home on the Beach"

Tropical Pool Villa

No Name in Paradise, 2 bdr house with private pool

3 Bed 3 Bath Villa | Private Pool | Pelican | SXM

Bungalow luxueux avec piscine privée
Private house rentals

Vista Azul SXM

Water access, snorkeling gear & kayaks

Villa Taïana - Oyster Pond

Villa Tamarind | Luxury | Spectacular Views | 4BDR

Comfortable beach house

Stunning Ocean View from Balcony & Pool - Sleep 10

Villa Terres Basses

THE HILL, 2 bedrooms, pool, panoramic views
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$62,544 GYD | G$48,738 GYD | G$57,523 GYD | G$57,105 GYD | G$56,896 GYD | G$41,835 GYD | G$61,916 GYD | G$62,125 GYD | G$26,147 GYD | G$41,835 GYD | G$41,835 GYD | G$57,523 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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