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House vacation rentals in Simpson Bay

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Top-rated house rentals in Simpson Bay

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Top guest favorite

An outdoor dining area is set for a meal with an expansive table that accommodates eight or more guests. The space features sleek chairs and offers unobstructed views of the ocean and horizon, framed by clear skies. The surrounding area reflects a serene coastal ambiance.

Home in Sint Maarten

5 out of 5 average rating, 38 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!*

A panoramic view of the turquoise sea is captured from the rooftop, with the coastline and palm trees visible in the foreground. Soft white clouds drift over the lush green mountains in the distance, creating a serene backdrop to the vibrant scene.

Home in Simpson Bay

4.92 out of 5 average rating, 12 reviews

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 commune 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.

A spacious bedroom is showcased with a large bed featuring neutral-toned linens. A panoramic window offers stunning views of the ocean and coastline, framed by soft drapes. A bedside table holds a lamp, and a television is positioned across the room, enhancing the modern decor.

Home in Upper Prince's Quarter

5 out of 5 average rating, 63 reviews

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!

Two lounge chairs are positioned on a wooden deck, facing the turquoise waters. A small table is placed between them, featuring decorative items. In the background, rocky coastline and distant hills are visible under a blue sky adorned with clouds.

Home in Marigot

4.92 out of 5 average rating, 13 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.

An outdoor lounge area features a modern pergola with plush seating and neatly arranged towels. The infinity pool, with its seamless edge, reflects the vibrant blue of the ocean under a clear sky, providing expansive views of the coastline and surrounding landscape.

Home in Upper Prince's Quarter

4.96 out of 5 average rating, 53 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.

Steps leading down to a sandy beach are framed by a white railing. The clear turquoise water laps gently at the shore, revealing a mix of sand and smooth stones. Bright sunlight illuminates the tranquil scene, highlighting the serene coastal atmosphere.

Home in Cole Bay

5 out of 5 average rating, 16 reviews

Pelican key - BEACH FRONT Villa

Stunning beachfront villa of 200 sqm, 6 steps away to the beach with private pool! New to the market and fully renovated, available from December 20th. It features 3 spacious, AC bedrooms, each with a smart TV and bathroom. Large living room opens onto the Caribbean Sea, whith fully equipped kitchen, dining area that seats 8 and a bar area to enjoy. The terrace is for outdoor living, with bbq, shaded dining area comfortable sofas and sun loungers directly to the beach & swimming pool.

A well-lit bedroom features a spacious bed with crisp white linens and various decorative pillows. Matching bedside tables hold stylish lamps. A wall-mounted television is positioned in front of the bed, while light streaming through partially opened shutters adds a bright touch to the room.

Home in Simpson Bay

5 out of 5 average rating, 14 reviews

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!

A modern villa exterior features a sleek infinity pool surrounded by a tiled terrace. A spacious dining area is set beneath a pergola, complemented by tropical plants and a distant hillside view. Sunlight reflects off the pool's surface, enhancing the inviting atmosphere.

Home in Sint Maarten

5 out of 5 average rating, 19 reviews

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.

Top guest favorite

A modern kitchen and living area are visible, featuring a large island with bar seating, complemented by pendant lighting. Floor-to-ceiling glass doors provide access to an outdoor terrace with ocean views. Natural light fills the space, enhancing the contemporary decor.

Home in Upper Prince's Quarter

5 out of 5 average rating, 17 reviews

Aman Oceanview

The Aman Oceanview is an oasis of calm, luxury and elegance, built into the hillside overlooking the sublime and sparkling Atlantic Ocean and Saint Barth. This a brand new modern property consists of two master bedrooms with two bathrooms, living room with fully equipped kitchen, exterior terrace and laundry area. All two bedrooms, the living room have unobstructed views of the ocean. A breathtaking infinity pool and a sundeck overlook the ocean, form the focal point of Aman

The villa is presented from an elevated angle, showcasing a private pool surrounded by a sleek patio. Large glass doors provide a view of the inviting interior, while sun loungers are placed alongside the pool, integrating seamlessly with the lush surroundings.

Home in Lowlands

4.74 out of 5 average rating, 122 reviews

SEA TRUE VILLA,Lavish,Sea view near Maho&Mulletbay

Luxurious Three-Bedroom Villa with Private Pool and Tropical Garden Indulge in Caribbean elegance at this one-of-a-kind villa, designed and built by the owner, a master craftsman in marble and precious stones. Featuring high-end finishes, a private pool, and a lush tropical garden, this villa offers the perfect blend of sophistication and comfort. Located just a 5-minute walk from vibrant Maho Village Daily room service included during high season (Dec 15–Apr 15).

Top guest favorite

An infinity pool reflects the bright blue sky and shimmering sea, creating a tranquil contrast. The edges of the pool are lined with clear glass panels, providing unobstructed views of the horizon. The sunlight sparkles on the water's surface, emphasizing the serene setting.

Home in Indigo Bay

5 out of 5 average rating, 20 reviews

Life's Good

Located in the only planned community in Sint Maarten in the beautiful and gated “Indigo Bay”. The whole villa to yourself and just 10 minutes from the airport. Villa "Life’s Good" with infinity pool is located on the mountainside with a 180 degree view of the sea and view of the Islands, Saba, St Kitts & Nevis and Sint Eustatius.. A spectacle of breathtaking sunrises and sunsets. Just a 3 minute drive from the villa: are beaches, restaurants and all amenities.

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

4.89 out of 5 average rating, 151 reviews

THE HILL HOUSE, 2 Bdr, pool, panoramic view

Accommodation with private 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!

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Popular amenities for Simpson Bay house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

A spacious swimming pool is surrounded by tropical plants and palm trees, gently swaying in the breeze. The clear blue water reflects the bright sky, and comfortable lounge chairs are positioned nearby. The area showcases a relaxed atmosphere, ideal for leisure and enjoyment.

Home in Collectivity of Saint Martin

5 out of 5 average rating, 22 reviews

Fantastic 2 bedroom villa, swimming pools, tennis

A private pool is framed by a wooden deck, with lounge chairs positioned for relaxation under the sun. A covered terrace area offers a dining table, enhancing outdoor living. Lush greenery surrounds the property, with a palm tree adding a tropical touch.

Home in Cul-de-Sac

4.9 out of 5 average rating, 20 reviews

Maison Ti Case, private pool, near Pinel Island

A refreshing freeform pool is bordered by tropical palm trees and decorative planters. A modern structure with transparent walls opens to the pool area, featuring a striking piece of wall art depicting a dog. The serene atmosphere is complemented by clear blue skies.

Home in Sint Maarten lowlands Maho

4.79 out of 5 average rating, 66 reviews

Villa Blue Lagoon SXM

Top guest favorite

An outdoor terrace features a sleek design with minimalist white seating arrangements and a shimmering pool. Tropical greenery frames the area, and expansive views of the ocean and sky create a serene backdrop. The layout encourages relaxation and enjoyment of the surrounding beauty.

Home in Collectivité de Saint-Martin

5 out of 5 average rating, 15 reviews

Prestigious Villa with Breathtaking Ocean View

The exterior of the villa showcases a multi-level design with large balconies and vibrant blue accents from the infinity pool. Lush greenery surrounds the property, while a well-maintained garden and pathway lead to the entrance. A wooden fence encases the yard, enhancing the private atmosphere.

Home in Little Bay

4.94 out of 5 average rating, 16 reviews

5B Oceanview villa near Philipsburg

A private pool is bordered by a terrace with lush palm trees and an outdoor dining area. The ocean view extends into the distance under a partly cloudy sky, with sunlight reflecting off the water's surface.

Home in Pelican Key

5 out of 5 average rating, 15 reviews

Pelican Pearl Villa with Pool and Generator

A private swimming pool is seen alongside a wooden deck, bordered by lush greenery and palm trees. Two lounge chairs are positioned for relaxation under the shade of a roof overhang, with outdoor dining furniture visible nearby, creating a seamless connection to the home's exterior.

Home in Anse Marcel

4.96 out of 5 average rating, 25 reviews

House - Private Pool & Sea View – Anse Marcel

Home in Upper Prince's Quarter

5 out of 5 average rating, 3 reviews

Villa Kanoa - 4 bedroom villa with Ocean View

Weekly house rentals

Two blue lounge chairs are positioned on a sandy beach, facing the turquoise sea. Gentle waves can be seen lapping at the shore, with green mountains visible in the background under a clear blue sky.

Home in Collectivity of Saint Martin

4.94 out of 5 average rating, 47 reviews

New! On the beach, 2 bedroom villa, sea view, pool

An open living space is featured, with a round dining table surrounded by six white chairs. A sleek black sofa is positioned near a window with horizontal blinds. A large floral artwork adorns the wall, complemented by a small green plant in the corner.

Home in Marigot

5 out of 5 average rating, 19 reviews

Spacious 3 Bedroom 2 Bathroom Marigot Home

Clear turquoise waters gently lap against a sandy shore, where fallen leaves in varied colors are scattered across the beach. The scene is framed by lush green foliage, offering a soothing natural backdrop.

Home in Grand Case

4.95 out of 5 average rating, 66 reviews

Comfortable beach house

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

4.86 out of 5 average rating, 57 reviews

ALOHA penthouse

A spacious terrace features wooden flooring, with comfortable seating arranged for relaxation. Lush greenery is visible alongside the edge, and a stunning view of the sea is showcased in the background, complemented by a partially cloudy sky.

Home in SAINT-MARTIN

4.89 out of 5 average rating, 9 reviews

Sunset View

Top guest favorite

The beach scene features soft white sand gently curving along a tranquil turquoise bay. Various shades of blue umbrellas and beach chairs dot the shoreline. A backdrop of colorful buildings and green hills adds to the coastal charm, while people enjoy the water and sun.

Home in Philipsburg

4.98 out of 5 average rating, 54 reviews

3-Bedroom Home In Philipsburg, Near the Beach

A crystal-clear swimming pool is set against a backdrop of the Caribbean Sea and distant hills. Blue lounge chairs are positioned along the pool deck, inviting relaxation. The vibrant blue sky above complements the serene landscape, enhancing the tranquil environment of the villa.

Home in Upper Prince's Quarter

4.97 out of 5 average rating, 71 reviews

Villa Tamarind | Luxury Oasis | Ocean views | 4BDR

A sunlit deck area surrounds a tranquil pool, featuring six lounge chairs arranged for relaxation. Lush tropical plants frame the scene, while distant ocean views are visible under a blue sky dotted with clouds.

Home in Cul-de-Sac

4.87 out of 5 average rating, 45 reviews

Luxury villa with ocean views

Private house rentals

A cozy bedroom features a spacious bed dressed in patterned linens, complemented by decorative pillows. Soft lighting from wall sconces creates a calming atmosphere. A small bedside table holds a remote, and a minimalist decor style is evident throughout the room.

Home in Cole Bay

4.78 out of 5 average rating, 40 reviews

Annettes B&B - Private | Wasmachine | Kingsize bed

A modern villa is depicted in a gated community, featuring a multi-level structure with large windows. An infinity pool is surrounded by several lounge chairs, and a patio area with dining furniture is visible. Lush greenery enhances the outdoor space.

Home in Upper Prince's Quarter

5 out of 5 average rating, 8 reviews

Ocean Pearl - Spacious Villa in Dawn Beach

A white gate opens to a sandy path leading to a turquoise ocean. Lush greenery frames the view, and a single tree stands on the left, creating a serene entryway to the beach.

Home in Simpson Bay

4.92 out of 5 average rating, 13 reviews

Coco's Beach House - Simpson Bay Beach

A spacious verandah features a comfortable seating area with a light-colored couch and a dark wicker coffee table. Lush greenery is displayed in a yellow planter, with panoramic views of the hills and bright blue sky in the background.

Home in Indigo Bay

4.77 out of 5 average rating, 175 reviews

La Pearle - Luxurious 1 Bedroom Condo By the Beach

A vibrant view of the coastline and distant hills is framed by the greenery of palm leaves and a tall cactus. The blue rooftops of nearby houses contrast with the clear blue water, creating a serene outdoor setting.

Home in Collectivité de Saint-Martin

4.93 out of 5 average rating, 28 reviews

NEW House 2 bathrooms, 3 terraces and ocean view

An inviting living area showcases comfortable seating with soft cushions arranged around a glass coffee table. A clean, open layout leads to a dining space in the background, while elegant wooden stairs ascend to the upper level, accented by decorative wall plates.

Home in Upper Prince's Quarter

4.94 out of 5 average rating, 49 reviews

Caribbean Style Family Home

A serene beach scene features rows of sun loungers adorned with white umbrellas set against soft, sandy shores. Gentle waves lap at the coastline, while palm trees sway softly in the breeze. The distant hills provide a scenic backdrop under a clear blue sky.

Home in Collectivité de Saint-Martin

5 out of 5 average rating, 7 reviews

Orient Bay-Villa 48 Esmeralda Resort-Accès Plage

Two sun loungers are positioned on a terrace overlooking a vibrant blue ocean. Lush greenery and colorful flowers frame the view, complementing the calm waves in the distance under a clear sky.

Home in Philipsburg

4.95 out of 5 average rating, 59 reviews

Villa Allamanda a Indigo Bay

Quick stats about house rentals in Simpson Bay

Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ147 before taxes and fees
Total number of reviews
660 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Wifi availability
20 properties include access to wifi

Destinations to explore