
House vacation 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!*

"Sweet Home on the Beach"
SITUATION Exceptionnelle. Vue sur la baie de Marigot Pieds dans l’eau Face à la Mer des Caraïbes Superbe plage de sable blanc, cocotiers, mer turquoise ATOUTS Maison duplex sur la plage Situation idéale pour visiter 4 Piscines 1 tennis Un beau jardin Résidence sécurisée 24H/24H Parking gratuit A côté : supermarché, boulangerie, restaurants Idéal pour Couple Famille ou Amis BON A SAVOIR A 2 kms de Marigot Voiture location conseillée Wifi, forfait ménage, serviettes, draps inclus dans le prix.

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..

Infinite Blue – Elegant Villa & Turquoise Views
Infinite Blue is an elegant 3-bedroom, comfortable villa with the perfect relaxing atmosphere. The kitchen is fully equipped, and all social areas are comfortable spaces, with a nice design and excellent ocean views. The terrace area has a spacious dining room (area), Inf. pool, outside BBQ, outside shower, and a jacuzzi 37 to 39 C degrees depending on the weather. For couples or families. The community location is great and safe! It is close to the main sites of interest.

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

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!

Modern 2-Bed Hilltop Apartment- Loma Vista
Escape to Loma Vista, a peaceful hilltop retreat just 5 minutes from Philipsburg and the beach. This spacious two-bedroom, two-bathroom home features a fully equipped kitchen, a bright living room and a large porch with stunning view. Tucked away in a quiet setting, it's the perfect spot to relax while staying close to everything the Island has to offer. The road leading to the apartment is a bit bumpy, but is definitely a safe drive up.

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 Simpson Bay house rentals
House rentals with a pool

Villa Coco • 3BR waterfront with kayaks, Wi-Fi, AC

ALMOND BLUE ...Pinel bay view - caribbean feeling

Villa close to the beach

4 Bedroom Luxury Villa, Sea Views, Pelican Key

Prestigious Villa with Breathtaking Ocean View

Cocon Lodge Elegant, Tropical Terrace, Sea View

MAHI-MAHI Logde, private pool, Orient Bay

Kanoa - Luxury 3 bedroom with backup generator
Weekly house rentals

Spacious 3 Bedroom 2 Bathroom Marigot Home

Quiet beachfront house

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

3-Bedroom Home In Philipsburg, Near the Beach

Villa Tukan, Baie Orientale Village

Villa Allamanda a Indigo Bay

House - Private Pool & Sea View – Anse Marcel

Fun times ahead! Devine in You Cupecoy is calling.
Private house rentals

Sunrise Over St. Barths

Villa Incognito on the Beach

Ocean Pearl - Spacious Villa in Dawn Beach

*NEW* SeaRenity Villa With Private Pool Indigo Bay

Water access, snorkeling gear & kayaks

La Cool & Douce SXM, Orient Bay.

C&S Spacious 3 BDR 2.5 BTHR with sea view

5B Oceanview villa near Philipsburg
When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R5,612 ZAR | R5,370 ZAR | R5,145 ZAR | R4,729 ZAR | R4,712 ZAR | R3,464 ZAR | R5,197 ZAR | R5,023 ZAR | R4,365 ZAR | R5,058 ZAR | R4,261 ZAR | R5,785 ZAR |
| 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 vacation rentals
Explore 20 vacation rentals in Simpson Bay

Nightly prices starting at
Simpson Bay vacation rentals start at R693 ZAR per night before taxes and fees

Verified guest reviews
Over 690 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!
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