
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.

Villa Turquoise Heaven
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.

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!*

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.

The beachcomber
Welcome to your perfect island retreat! Located in the heart of Beacon Hill, this cozy unit offers the ideal home base for exploring all that Sint Maarten has to offer. Just steps away from the island’s top attractions, you'll be within walking distance to: Maho Beach, Casinos,Restaurants & Bars. This unit is perfect for couples or solo travelers. Don’t miss out on the best location on the island – book your stay in Beacon Hill today and live like a local just steps from the action!

New-Sunset Place Villa w Stunning Waterfront Views
Sunset Place is a lovely waterfront villa located within the exclusive gated beachfront community of Pelican Cove on St. Maarten’s beautiful Coast. The villa is on one level, fully air-conditioned includes a comfortable living/dining room, open kitchen and generator. 3 bedrooms, 3 bathrooms, swimming pool on the sea with spectacular views of the sunset. Quality designer furniture - 10 minutes from the airport - Supermarkets - Casinos - Clubs - Bars - Restaurants 5 minutes away..

Aman Oceanview
The Aman Oceanview is an oasis of calm, luxury and elegance, built into the hillside overlooking the sublime and sparkling Atlantic Ocean and Saint Barth. This a brand new modern property consists of two master bedrooms with two bathrooms, living room with fully equipped kitchen, exterior terrace and laundry area. All two bedrooms, the living room have unobstructed views of the ocean. A breathtaking infinity pool and a sundeck overlook the ocean, form the focal point of Aman

“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!

Blu Azur : Your Dream Villa on the Lagoon
Offrez-vous un séjour inoubliable dans une villa d’exception située au cœur de Maho, l’un des endroits les plus prisés de la "Friendly Island". Laissez vous séduire par sa vue exceptionnelle sur le lagon, la mer des Caraibes et l'ile d'Anguilla. Entièrement rénovée et meublée avec goût, cette demeure spacieuse et chaleureuse est parfaite pour accueillir des groupes, que ce soit en famille ou entre amis. Un cadre idyllique qui rendra chacun de vos instants unique !

Life's Good
Located in the only planned community in Sint Maarten in the beautiful and gated “Indigo Bay”. The whole villa to yourself and just 10 minutes from the airport. Villa "Life’s Good" with infinity pool is located on the mountainside with a 180 degree view of the sea and view of the Islands, Saba, St Kitts & Nevis and Sint Eustatius.. A spectacle of breathtaking sunrises and sunsets. Just a 3 minute drive from the villa: are beaches, restaurants and all amenities.

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!

THE HILL HOUSE, 2 Bdr, pool, panoramic view
Accommodation with private pool and breathtaking views Treat yourself to a dream break at this stylish home, nestled in the secure Almond Grove Estate neighborhood. Enjoy 2 air-conditioned bedrooms, a bright living room, a full kitchen, and especially an idyllic outdoor space with a pool and panoramic views of Simpson Bay. Just 5 min from Marigot, 10 min from the airport and 15 min from the beaches, it is the perfect address for an unforgettable stay!

Villa Josefa SXM · Ocean View Above Friar’s Bay
✨ Perched above Friar’s Bay, this villa offers a breathtaking view from Maho to Anguilla. 🏡 3 ocean-view master suites, kitchen ready for a private chef. Upstairs, a covered terrace becomes a peaceful refuge facing the sea for up to 10 guests. 🌊 Pool surrounded by a suspended deck, pergola & evening serenity. 🌴 Gated residence, beaches within walking distance. Here, luxury, nature and sunsets are lived more than described.
Popular amenities for house rentals in Simpson Bay
House rentals with a pool

Slowlife! Blooming Villa! Your ideal vacation home

Villa close to the beach

Quiet beachfront house

4 Bedroom Luxury Villa, Sea Views, Pelican Key

Water access, snorkeling gear & kayaks

"La Vue SXM" Paradise "Villa Rosa" 5 bedroom rate

Villa Allamanda a Indigo Bay

Kanoa - Luxury 3 bedroom with backup generator
Weekly house rentals

Spacious 3 Bedroom 2 Bathroom Marigot Home

Maison Ti Case, private pool, near Pinel Island

NEW House 2 bathrooms, 3 terraces and ocean view

Sea La’Vie — 2mins walk from the beach!

3-Bedroom Home In Philipsburg, Near the Beach

*NEW* SeaRenity Villa With Private Pool Indigo Bay

5B Oceanview villa near Philipsburg

MAHI-MAHI Logde, private pool, Orient Bay
Private house rentals

Sunrise Over St. Barths

Villa Louisiana

Villa Saba, dream vacation between the sea and the mountains

Villa Tamarind | Luxury Oasis | Ocean views | 4BDR

Atypik Villa

Palm Paradise - Tropical Villa in Oyster Pond

Ocean

Ocean view villa at Dawn beach
When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $421 SGD | $403 SGD | $386 SGD | $355 SGD | $354 SGD | $260 SGD | $390 SGD | $377 SGD | $328 SGD | $380 SGD | $320 SGD | $434 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 |
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 $52 SGD per night before taxes and fees

Verified guest reviews
Over 690 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

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