House vacation rentals in Simpson Bay

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Top-rated house rentals in Simpson Bay

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Guest favorite

The living room features a comfortable arrangement of light-colored sofas adorned with pillows and throws. A large flat-screen TV is mounted on the wall. Large glass sliders open to reveal sweeping ocean views, enhancing the inviting atmosphere.

Home in Sint Maarten

5 out of 5 average rating, 26 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 favorite

An outdoor terrace is presented with white loungers and a table, overlooking the sandy beach and turquoise water. Sailboats can be seen in the distance against a clear blue sky. The setting offers a tranquil and relaxing atmosphere near the sea.

Home in Marigot

4.88 out of 5 average rating, 8 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 favorite

The exterior of a modern property is showcased against a vibrant sunset sky. Soft outdoor lighting highlights the architectural design. A manicured lawn and paved path lead towards the ocean view, creating a serene connection with nature and the surrounding landscape.

Home in Upper Prince's Quarter

4.95 out of 5 average rating, 42 reviews

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.

Superhost

A private wooden deck features comfortable seating with light-colored cushions, surrounded by vibrant green plants. A white table is adorned with a decorative lantern and a small arrangement of plants, creating a serene atmosphere under the evening sky.

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 favorite

A row of comfortable lounge chairs are positioned beside a serene infinity pool, offering views of the expansive Caribbean Sea and clear blue sky. The area is surrounded by stone tiles, enhancing the outdoor relaxation space.

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.

Top guest favorite

A spacious living room features a light color palette with plush sectional seating and modern decor. Floor-to-ceiling sliding glass doors invite natural light and provide views of the surrounding landscape. A flat-screen TV is mounted on the wall, enhancing the room's contemporary feel.

Home in Little Bay

5 out of 5 average rating, 9 reviews

5B Oceanview villa near Philipsburg

Hilltop Villa w/ Stunning Ocean & Pond Views Near Philipsburg Welcome to your dream getaway in St. Maarten/St. Martin! Perched atop a picturesque hill, this villa offers nearly 3,000 square feet of interior space, a 1,200 square foot sun deck, and an infinity pool. Enjoy breathtaking views of the ocean, pond, and lush hillsides. With over 500 square feet of balcony and terrace outdoor space, this spacious retreat is ideal for families or friends seeking a peaceful, luxurious island escape.

Superhost

An aerial view of the villa showcases a private pool surrounded by a spacious terrace. Lounge chairs and a hammock are visible, with glass railings enhancing the open feel. The lush greenery and distant mountains provide a scenic backdrop under a clear blue sky.

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.

Superhost

A spacious terrace is showcased, featuring a hammock and several white chairs. A view of the sky and distant buildings is visible, with an airplane appearing above the horizon. The tiled floor reflects a warm tone, enhancing the outdoor space.

Home in Lowlands

4.85 out of 5 average rating, 53 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

Aerial view of Villa Paradis showcases its vibrant red exterior nestled among tropical greenery. The property features a spacious outdoor area with a private pool, surrounded by colorful flowers and a well-maintained garden. The surrounding hills provide a harmonious backdrop, enhancing the natural setting.

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 favorite

The upper-level house is framed by palm trees and surrounded by a spacious, paved area. A staircase leads to the entrance, while multiple seating arrangements are positioned on the balcony. The blue sky and ample sunlight create a vibrant setting.

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 favorite

A spacious outdoor seating area features comfortable wicker furniture, including a circular sofa and lounge chair. Lush tropical plants and vibrant flowers provide a scenic backdrop, while distant green hills are visible under a partly cloudy sky. A glass coffee table sits centrally among the seating.

Home in Calabash Rd, Cole Bay

4.93 out of 5 average rating, 141 reviews

THE HILL HOUSE, 2 Bdr, pool, panoramic view

Your private oasis with pool and breathtaking views Treat yourself to a dream getaway in this elegant house, 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!

Superhost

A refreshing swimming pool is set against a backdrop of the Caribbean Sea, with clear blue water reflecting the sky. Bright foliage partially frames the pool area, adding a touch of greenery to the serene outdoor space, which features a stone wall and unobstructed sea views.

Home in Cole Bay

4.86 out of 5 average rating, 29 reviews

Luxury, Villa Panoramic Sea Views, Pelican Key

Welcome to Villa del Mar, a luxurious executive home offering breathtaking panoramic views of the Caribbean Sea and stunning sunsets. From this exquisite property, you can see the islands of St. Barts, Nevis, St. Kitts, St. Eustatius, and Saba. Nestled in the premier residential area on the Dutch Side, it provides easy access to vibrant attractions and beautiful beaches while ensuring privacy and tranquility.