House vacation 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.

0 of 0 items showing

1 of 3 pages

Guest favourite

Home in Sint Maarten

5 out of 5 average rating, 20 reviews

Luxury Villa "Villamour" w/ Private Pool

Villamour is a brand new, multilevel 5 bed, 4.5 bath villa overlooking the Caribbean Sea. You can watch boats and cruise ships sail by from the comfort of your private pool and patio. The villa was decorated by a top interior designer in South Florida. It is modern, chic, and inviting. It is only a 5 min walk to the beach and a short drive to restaurants, nightlife, supermarkets, & shopping. Top chef available for booking. This is an ideal spot for a romantic getaway or a group/family vacation.

Guest favourite

Home in Orient Bay

4.88 out of 5 average rating, 51 reviews

Paradise View, Creole house and private pool

Spacious independant house with private swimming pool 5 min walk from Orient Bay. Magnificent view on the surrounding beaches and islands. Softness of the Caribbean breeze. Lots of space with a large 600 sq ft deck to relax facing the sea. Kitchen and dining room of 250 sq ft open very widely onto the terrace. Large conditioned & ventilated living room of 350 sq ft with large sofa bed and bathroom. Upstairs, large, very bright conditioned bedroom of 350 sq ft with its office space and bathroom.

Guest favourite

Home in Sint Maarten

5 out of 5 average rating, 15 reviews

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!*

Guest favourite

Home in Marigot

5 out of 5 average rating, 5 reviews

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.

Guest favourite

Home in Phillipsburg

4.94 out of 5 average rating, 33 reviews

Villa Fleur de Mer Endless Ocean view /Priv. Pool

Villa Fleur de Mer is one of Sint Maarten's top-rated Villas. Private estate villa with a breathtaking 180-degree ocean view! Seclusion and tranquility, tempered by cool ocean breezes, with a private pool. Enjoy this adventurous yet tranquil paradise home between France and Holland. Spectacular views of the Atlantic Ocean with an unparalleled view of St. Barths. Minutes drive to downtown Phillipsburg and the French side. Enjoy the video below and Welcome, Home! https://fb.watch/7uxXstBra7/

Guest favourite

Home in Upper Prince's Quarter

4.92 out of 5 average rating, 25 reviews

Teresa’s Ocean Paradise

St. Maarten’s best kept secret with spectacular 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.

Superhost

Home in Cole Bay

4.89 out of 5 average rating, 9 reviews

Charming Cottage with large deck in quiet area

Charming one bedroom house with private deck situated in the beautiful and quiet residential community of Almond Grove with 24 hour gated security. A 5 minute walk to the main road one will find a bus stop as well as some restaurants and small grocery stores. Beaches and nightlife are a short drive away. The unit has wifi, Flat screen television with many channels & movies as well as Apple TV and netflix, a portable BOSE blue tooth speaker, Gas BBQ grill, etc. Beach towels are provided.

Superhost

Home in Saint Martin

5 out of 5 average rating, 3 reviews

La maison de l 'île

Welcome to our home away from home! Sint Maarten has been our favorite island getaway for several years and we are excited to share it with you! This spacious 6 bedroom newly renovated home has panoramic Caribbean Sea views and breezes. Spend the day at the pool watching boats pass by with distant views of St Barths. The home is located in a gated community in Dawn Beach, close to the French line and some amazing quaint, local restaurants and tucked away from the tourist hustle-bustle.

Superhost

Home in Lowlands

4.85 out of 5 average rating, 46 reviews

ALOHA penthouse

The penthouse up for rent is situated in the heart of the Maho area in St. Maarten. It is called the Aloha penthouse apartment and has 2 levels with a large terrace on top. The photos will give you a good idea of what the premises have to offer. The apartment has been fully renovated in November-December 2019. It has been outfitted with all the amenities that you can expect of a superb vacation location. Your host (Paul) is the owner and lives in the adjacent house and is always available.

Superhost

Home in Pic Paradis

4.91 out of 5 average rating, 34 reviews

Newly Renovated! Villa Paradis - A jungle getaway.

Welcome to the newly renovated Villa Paradis, a different side of St. Martin! Discover breathtaking views and be surrounded by nature. A unique experience with iguanas in the trees and the sound of monkeys echoing through the valley. This exclusive property is the nature lover's paradise, ideal for those seeking to get away from it all while being centrally located only 10 mins from the beach. *Spa services/private chef available *No children *No parties Social Media: #theparadisepeak

Guest favourite

Home in Great Bay Beach

4.86 out of 5 average rating, 57 reviews

PrivateHome In Greatbay FreeWi-fi &Private Parking

The Cosy’Nest is located just one minute away from the Great Bay beach; four minutes away from the boardwalk. The Bobby's Marina for boat excursions and water transfers is also in the area. Explore Historic sites like Fort Amsterdam and Fort Willem. Experience Island Style living on this ideal family estate. This Unique, Single Family Home is perfect for that romantic getaway or retreat of 2 to 4 persons. With its Franco-Dutch essence, you will love this modern Caribbean experience.

Superhost

Home in Sint Maarten

5 out of 5 average rating, 3 reviews

Villa Twin Palms

Twin Palms’ offers a unique opportunity to enjoy your own private & luxurious tropical villa while enjoying breathtaking and endless ocean views. The villa is tucked into the beautiful hillside inside the secluded ‘Dawn Beach Estates'. The tropical garden leads to the beach. This villa is a 2 bedroom ensuite and a studio apartment. The villa can sleep up to 6 guests. You can enjoy this villa by renting 2 or 3 bedrooms the 3rd bedroom is an additional rate of $115 per night.