
House holiday rentals in Simpson Bay
Find and book unique houses on Airbnb
Top-rated house rentals in Simpson Bay
Guests agree: these houses are highly rated for location, cleanliness and more.

Townhouse Villa LX
Superbe Maison mitoyenne, faisant partie d’une petite copropriété sécurisée dans le quartier de Beacon Hill. Située à 5 minutes de l’aéroport, vous pourrez admirer le ballet unique des avions au dessus de la plage de Maho, sans nuisances sonores, depuis la piscine partagée installée sur un rooftop. Très spacieuse avec ses 3 belles chambres, 2 salles de bain, entièrement climatisée, terrasse arborée et cuisine équipée. Située à proximité des restaurants et clubs. Accès plage direct en 1 minute.

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!*

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!

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.

Luxury Bungalow with Amazing Seaview & Pool
Come and enjoy our very comfortable modern Kombawa Bungalow with his spacious bathroom, fully equipped kitchen, covered terrace and amazing view with gorgeous sunsets. The huge pool and peaceful garden will assure you a perfect relaxing stay. It’s located in a very secure gated community, 5 minutes walking distance from the beautiful plum bay beach. On the French side but still only a few minutes from the Dutch side and all convenient stores, gas station, restaurants, pharmacy, beauty salon…

2 Bedroom Ocean Front Villa, Private Infinity Pool
Clearwater is a cliffside waterfront property with one of the most spectacular views on the island! Overlooking Great Bay, Philipsburg, Divi Little Bay, the turquoise Caribbean Sea and the magnificent cruise ships, this one-of-its-kind location will be sure to Wow you. It is perfectly situated for easy access to all SXM has to offer; 2 nearby beaches, restaurants, grocery stores, downtown shopping, bars and entertainment. If you are interested, checkout the 3 Bedroom option here on Airbnb.

Soleil & Sage Haven,2BR 2.5BH Townhouse in Cupecoy
Located in one of SXM's upscale neighborhoods, Cupecoy, this rental is an absolute treat for any vacationer! Having two of the most beautiful beaches on the island, Mullet Bay & Cupecoy Beach few minutes away, excellent location for snorkeling. Private Plunge Pool, Rooftop Terrace & Bbq grill for personal use. This amazing town house is also located within a short distance of the popular Maho Beach where you can watch the planes land over the beach. It is truly a vacationer's paradise!

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.

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 !

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!
Popular amenities for house rentals in Simpson Bay
House rentals with a pool

Life's Good

Ocean View House 3 Terraces/2BR/2BA - Shared Pool

Sunset View

Prestigious Villa with Breathtaking Ocean View

Red Rock Villa: 3 bedrooms & private pool

Luxurious Villa "Sea La Vie"

Villa Tamarind | Luxury Oasis | Ocean views | 4BDR

Kanoa - 3 bedroom Remote Luxe Escape
Weekly house rentals

Oceanview Paradise - Villa Del Sol w/ Generator

Fantastic 2 bedroom villa, swimming pools, tennis

Modern 2-Bed Hilltop Apartment- Loma Vista

Spacious 3BR with Private Cozy Pool

Blue Palm Estate Townhouse w/ Ocean View

5B Oceanview villa near Philipsburg

Modern artist's villa

Palm Paradise - Tropical Villa in Oyster Pond
Private house rentals

Villa Paradis - The best views of the island!

Quiet beachfront house

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

Villa Carib sxm piscine.

3-Bedroom Home In Philipsburg, Near the Beach

Villa Tukan, Baie Orientale Village

“Les Medes” 3 bedroom in Beautiful Beacon Hill

House - private pool & sea view - Anse Marcel
When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $416 SGD | $398 SGD | $381 SGD | $350 SGD | $349 SGD | $257 SGD | $380 SGD | $381 SGD | $160 SGD | $375 SGD | $316 SGD | $428 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 $51 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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