House holiday rentals in Simpson Bay

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Top-rated house rentals in Simpson Bay

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Guest favourite

Home in Sint Maarten

4.93 out of 5 average rating, 30 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 Sint Maarten

5 out of 5 average rating, 24 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, 6 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 Cul-de-Sac

5 out of 5 average rating, 24 reviews

Waterfront property with water access & kayaks

Shallow turquoise waters, untouched island, beach clubs and cocktails, sand bank, pelicans and turtles. What else could you possibly need? Oh, yes: a place to stay. Villa Ti Case is a new 5 bedrooms waterfront holiday rental, located in a gated luxury residence occupied by private houses, holiday rentals and hotels. Less than 5 min drive to: French bakery, restaurants and beach bars, beaches, grocery stores, souvenir and clothing shops, boat charters, water sports, equestrian center, hikes.

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.

Guest favourite

Home in Saint Martin

5 out of 5 average rating, 7 reviews

The Island House

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 Les Terres Basses

5 out of 5 average rating, 6 reviews

Villa Ellia - Modern luxury in St Martin FWI

Located in the prestigious Lowlands, this villa is your dream vacation spot with its breath-takings views on our beautiful green mountains. The villa is 5 minutes away from beaches, supermarkets, gyms, and activities. We will take great pleasure in hosting you. When renting with us you get concierge services to facilitate all things during your stay. Villa Ellia has 4 bedrooms and 4 bathrooms, the master bedroom and the kitchen have direct access to the large terrace and the private pool.

Guest favourite

Home in Great Bay Beach

4.87 out of 5 average rating, 60 reviews

The CosyNest 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 Pic Paradis

4.92 out of 5 average rating, 36 reviews

Newly Renovated! Villa Paradis - A jungle getaway.

Welcome to the newly renovated Villa Paradis, a different side of St. Martin! Discover unbeatable views of the islands below. 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 Simpson Bay

4.8 out of 5 average rating, 5 reviews

“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!

Guest favourite

Home in Calabash Rd, Cole Bay

4.93 out of 5 average rating, 139 reviews

THE HILL HOUSE, 2 Bdr, pool, panoramic view

Your private oasis with 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!

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. It is a private estate villa with a breathtaking 180-degree ocean view! You have seclusion and tranquility, 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. It is only a few minutes drive to downtown Phillipsburg and the French side.