
House vacation rentals in Simpson Bay
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Top-rated house rentals in Simpson Bay
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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.

Casa Rish-2BR 2.5BH TownHouse with pool in Cupecoy
This brand new gorgeous town house is located in the sought-after area of Cupecoy. Offering a perfect blend of comfort, convenience & Caribbean charm for a memorable stay. This house will bring your Caribbean dream vacation come true. It is walking distance to the Cupecoy beach. It has a private plunge pool and a rooftop terrace with great lagoon views. It is a Combination of charming and contemporary that fits perfectly to your weekend getaways, staycation, business trip or work from home.

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.

La Villa du Lagon : cosy villa for 8 people
Ravissante villa située à la baie Nettlé, parfait pour un séjour en famille ou entre amis. Chaque pièce de cette maison a été décorée avec des meubles et des éléments de décoration de très haute qualité, créant une ambiance luxueuse et chaleureuse. Quatre belles chambres, un salon spacieux, une belle cuisine très bien équipée, une belle terrasse couverte et non couverte, une piscine et un jacuzzi : tout est prévu pour que vous passiez un séjour inoubliable dans notre "Friendly Island".

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!

Caribbean Style Family Home
This lovely dwelling is a Caribbean style home with a modern tropical twist; Ideal for groups/families looking for real Caribbean experience. located in a quiet residential area (+valley view) with a private enclosed yard, parking and backyard with home grown organic herbs for natural teas. Come and live like a local among the locals: A 7 minute drive to our beautiful boardwalk beach in Philipsburg and its duty free shops. 7-10 mins to the famous orient beach.

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!

Simpson Bay Yacht Club condo
This beautiful 2 bed - 2 bath luxurious condo in Simpson Bay Yacht club (SBYC) is located in the best spot of the island. 2 bedrooms with king size beds, we can also add a crib. SBYC has 3 pools and 2 tennis courts for you to use. The Beach is at 5 min walking and so are supermarkets, restaurants, bakeries, bars, casinos etc. This is the perfect 2bdr house if you want to enjoy all of SXM. This condo has everything you need.

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 Coral | Collection Villas Saint-Martin
Carefully designed, Villa Coral offers two spacious and comfortable bedrooms, perfect for two couples looking travelling as a group, or a small family. The villa's elegant pool (4.30 m x 13.32 m / 14' x 43') provides a serene space to unwind, and its length is ideal for those who enjoy a few laps in complete privacy.
Popular amenities for Simpson Bay house rentals
House rentals with a pool

Villa Paradis - The best views of the island!

ALMOND BLUE ...Pinel bay view - caribbean feeling

Villa close to the beach

Villa Louisiana, Orient Bay

Sea Shell Villa- Grand Case

2 Bedroom Ocean Front Villa, Private Infinity Pool

MAHI-MAHI Logde, private pool, Orient Bay

"Sweet Home on the Beach"
Weekly house rentals

Spacious 3 Bedroom 2 Bathroom Marigot Home

Comfortable beach house

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

Casa Bay Studio, Cole Bay

Coco's Beach House - Simpson Bay Beach

3-Bedroom Home In Philipsburg, Near the Beach

House on Orient Bay, ideally located

Coconut Beach Villa Sxm
Private house rentals

Villa Prospère

Peaceful Paradise

Villa Incognito on the Beach

VILLA CECILIA

Luxury Villa "Villamour" w/ Private Pool

Victoria Villa with private pool

Villa Myles Maho Beacon Hill

Stunning 7 BR Beachfront Villa w/Pool
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$62,532 GYD | G$48,729 GYD | G$57,513 GYD | G$57,095 GYD | G$56,886 GYD | G$41,828 GYD | G$61,905 GYD | G$62,114 GYD | G$26,142 GYD | G$41,828 GYD | G$41,828 GYD | G$57,513 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 |
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$12,548 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!
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