House holiday rentals in Simpson Bay

4.87 out of 5 average rating, 47 reviews

The private patio features a saltwater pool with ocean views, complemented by lounge chairs and tropical plants. Soft clouds drift overhead, enhancing the serene atmosphere. Nearby, a dining area offers an inviting space for meals while overlooking the lush garden and the expansive sea.

Home in Koolbaai

Luxury Villa Turquoise Heaven in Pelican Key

Welcome to Villa Turquoise Heaven- Modern Luxury in Pelican Key, SXM Experience the pinnacle of Caribbean elegance at Villa Turquoise Heaven, the newest luxury villa in the exclusive Tepui Residence. Designed for relaxation and style, this modern retreat offers a seamless blend of indoor-outdoor living with unparalleled views of the turquoise Caribbean Sea. From waking up to the gentle sound of waves to savoring sunsets from your private infinity pool, Villa TH offers an unforgettable escape.

An open-plan living area showcases a modern kitchen with a marble countertop and sleek cabinetry. Large glass doors provide expansive ocean views and access to an outdoor terrace. A comfortable seating area includes neutral-toned furnishings, while dining space is set for meals with panoramic vistas.

4.98 out of 5 average rating, 44 reviews

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.

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.

4.99 out of 5 average rating, 106 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!

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.

4.99 out of 5 average rating, 72 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!*

5.0 out of 5 average rating, 4 reviews

Home in Indigo Bay

Indigo Bay Condo Shamrock 2 Bed 2 Bath Ocean Views

Welcome to Condo Shamrock, a refined luxury vacation rental in Indigo Bay, St. Maarten, where modern comfort meets Caribbean elegance. This 2-bedroom, 2-bathroom residence offers panoramic ocean views, upscale finishes, and access to Indigo Bay’s exclusive gated community. Whether you’re visiting St. Maarten for romance, family time, or a long island escape, Condo Shamrock provides the perfect blend of style, security, and serenity.stylish experience at this centrally-located place.

4.95 out of 5 average rating, 22 reviews

A serene coastal view is captured, showcasing the shimmering blue ocean under a clear sky. Lush greenery and well-maintained gardens are visible in the foreground, while white buildings with decorative elements rest subtly along the coastline.

Home in Koolbaai

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!

4.79 out of 5 average rating, 219 reviews

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

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!

A tranquil pool reflects the azure sky and distant boats. Surrounded by lush greenery, the pool area features a cascading waterfall and is bordered by smooth stones. A wooden partition provides privacy, enhancing the serene atmosphere of the waterfront retreat.

4.89 out of 5 average rating, 100 reviews

ALMOND BLUE ...Pinel bay view - caribbean feeling

Relax in the Caribbean in this beautiful house with its extraordinary view of Pinel Bay, voted the 3rd most beautiful destination in the Caribbean. In the middle of a nature reserve overlooking St Barthélémy, you will swim with turtles and exotic fish. With access to the sea below the house, you can enjoy the kayaks available to go and enjoy a lobster or cocktail in one of the 2 restaurants on Pinel Island. St Martin – The Pearl of the Caribbean!

4.83 out of 5 average rating, 23 reviews

Home in Koolbaai

3 Bed 3 Bath Villa | Private Pool | Pelican | SXM

(Formerly Villa Domila) This stylish Caribbean villa is perfect for group or family trips. Horizon View Villa is spacious and modern with ocean views, set in the exclusive community of Pelican Key. Just minutes from lively Simpson Bay, it still feels like a secluded escape. Enjoy your own pool, all-day sun, and unforgettable sunsets over the sea. The villa is completely private, no shared spaces, just your own peaceful slice of paradise.

4.8 out of 5 average rating, 25 reviews

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

Townhouse Villa LX

Beautiful townhouse, part of a small secure condominium in the Beacon Hill neighborhood. Located 5 minutes from the airport, you can admire the unique ballet of planes over Maho Beach, without noise pollution, from the shared rooftop pool. Very spacious with 3 beautiful bedrooms, 2 bathrooms, fully air-conditioned, wooded terrace and equipped kitchen. Located close to restaurants and clubs. Direct beach access in 1 minute.

4.91 out of 5 average rating, 70 reviews

Home in Saint Martin

Slowlife! Blooming Villa! Freshly Renovated

Located in Terres Basses, near Baie Rouge beach, and with a magnificent view of the ocean, you will find a fully private 2 bedrooms, 2 bathrooms villa, ideal place for a family, couples or friends. With a large covered terrace, a pretty salt water swimming pool in the middle of a deck, all in the heart of a tropical garden, where you will definitely enjoy the wonderful ocean view that will allow you to relax.

5.0 out of 5 average rating, 4 reviews

Home in Lowlands

Villa Calma – Lagoon view, pool & tranquility

Villa Calma is a spacious, fully air-conditioned 3-bedroom, 3-bathroom villa offering breathtaking views of the lagoon, a private pool, multiple terraces, and a private dock with a boat lift. Conveniently located in the ultra-secure and very quiet area of Point Pirouette, right next to Maho and the airport, the villa is appealing thanks to its beautiful layout and abundant natural light.

Popular amenities for Simpson Bay house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Luxe

Home in saint martin

Villa Josefa SXM · Ocean View Above Friar’s Bay

5.0 out of 5 average rating, 29 reviews

5.0 out of 5 average rating, 5 reviews

Home in Cul-de-Sac

Villa ELIOS 2BR SeaView

4.97 out of 5 average rating, 36 reviews

Home in Indigo Bay

SeaRenity Villa With Private Pool Indigo Bay

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.

4.96 out of 5 average rating, 76 reviews

Teresa’s Ocean Paradise

4.94 out of 5 average rating, 36 reviews

A private pool is framed by timber decking, with two wooden lounge chairs featuring light blue cushions positioned nearby. Tropical plants and palm trees surround the area, contrasting against a bright blue sky scattered with fluffy white clouds, while distant views of the sea are visible.

Home in Cul-de-Sac

Villa Pandora

4.9 out of 5 average rating, 59 reviews

A serene view showcases a pool surrounded by lush palm trees, leading to the tranquil ocean. Colorful lounge chairs and shaded cabanas are positioned poolside, providing relaxation options. The bright blue sky is dotted with soft clouds, enhancing the overall scenic beauty.

Home in Cupecoy

Fun times ahead! Devine in You Cupecoy is calling.

5.0 out of 5 average rating, 7 reviews

Home in BAIE NETTLE

Sweet Home on the Beach rdc

5.0 out of 5 average rating, 32 reviews

A refreshing pool area is surrounded by palm trees and colorful tropical plants. Lounge chairs are positioned near the pool, offering views of the turquoise Caribbean Sea and nearby coastline. Natural light illuminates the space, emphasizing the vibrant outdoor environment.

Home in Philipsburg

2 Bedroom Ocean Front Villa, Private Infinity Pool

Weekly house rentals

4.94 out of 5 average rating, 17 reviews

Home in Cole Bay

Villa Kansha | 3BR Wellness Escape & Hot Tub

4.93 out of 5 average rating, 85 reviews

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

3-Bedroom Home In Philipsburg, Near the Beach

4.79 out of 5 average rating, 39 reviews

A spacious covered balcony is presented with comfortable seating arrangements, featuring a neutral-toned sofa and armchairs. A small table sits at the center, and potted plants accentuate the area. The ocean and scenic surroundings are visible beyond the railing, capturing the tranquil vibe of the outdoors.

Home in Pelican Key

3BR Townhouse in Pelican Key

4.85 out of 5 average rating, 74 reviews

Home in Lowlands

ALOHA penthouse

4.81 out of 5 average rating, 16 reviews

A spacious outdoor area is featured, showcasing a private pool surrounded by comfortable lounge chairs made of natural materials. A dining set is visible in the background, with a lush green hillside complementing the serene setting under a clear blue sky.

Home in Saint Martin

Villa.lalabay Mont Vernon 3, Saint-Martin

4.97 out of 5 average rating, 36 reviews

A spacious pool area is highlighted by a large swimming pool, surrounded by a wooden deck. A sun lounger is positioned nearby, featuring a folded towel on it. The backdrop showcases the villa's white exterior and a bright blue sky with fluffy clouds.

Home in Mont Vernon

Atypik Villa

5.0 out of 5 average rating, 17 reviews

The open-concept kitchen features a central island with modern appliances and ample storage. A cozy seating area is positioned nearby, with natural light flowing in from large sliding doors leading to a furnished terrace, creating a seamless connection between indoor and outdoor spaces.

Home in Saint Martin

2 bedroom villa on the beach!

5.0 out of 5 average rating, 14 reviews

Home in Anse Marcel

Ocean view house

Private house rentals

Home in Les Terres Basses

A private terrace is framed by lush greenery, showcasing a sleek infinity pool with a stone edge. Two lounge chairs are positioned nearby, complemented by a small seating area. A modern entrance leads to the interior space, under a bright blue sky with scattered clouds.

Luxurious bungalow with private pool

4.96 out of 5 average rating, 84 reviews

4.96 out of 5 average rating, 45 reviews

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

Spacious 3 Bedroom 2 Bathroom Marigot Home

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.

4.96 out of 5 average rating, 83 reviews

Villa Tamarind | Luxury | Spectacular Views | 4BDR

4.77 out of 5 average rating, 35 reviews

Home in Cole Bay

4 Bedroom Luxury Villa, Sea Views, Pelican Key

4.9 out of 5 average rating, 21 reviews

A private pool is positioned beside a dining area, featuring a table with seating for six. The space is framed by large windows that offer views of surrounding mountains and the nearby town. Light filters through overhead slats, creating a pattern across the floor.

Home in Philipsburg

Bahia - Villa 3

4.97 out of 5 average rating, 38 reviews

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

House - Private Pool & Sea View – Anse Marcel

A scenic view of the turquoise Caribbean Sea is framed by palm trees and lush greenery. A circular swimming pool reflects the vibrant blue sky, while two lounge chairs sit nearby, inviting relaxation in this serene outdoor setting.

4.71 out of 5 average rating, 42 reviews

Villa Simone