Villa holiday rentals in Simpson Bay

4.95 out of 5 average rating, 80 reviews

A private pool is bordered by a spacious patio area, featuring two lounge chairs. Expansive ocean views are visible in the background, with lush greenery surrounding the space. A dining table is situated under a covered area, providing a shaded option for meals outdoors.

Villa in Indigo Bay

Villa Ocean - Indulge Yourself in Paradise

A three-bedroom, two-bathroom beauty overlooking beach/vast views of the ocean in Indigo Bay. Sunset viewing on the deck, private pool or down to the beach 10 min by walking. 10 min to airport, night life, other popular beaches. Close to town. groceries, restaurants. All the bedrooms have a view of beach and the ocean. There is free wireless internet, TV, air conditioning, a dishwasher, refrigerator, microwave, wine refrigerator, coffee maker, washer dryer, outdoor gas grill and private parking.

LocationValueOutdoor spaces

5.0 out of 5 average rating, 17 reviews

Villa in Philipsburg

Ocean View Villa Little Bay

🌴 Villa Little Bay – Oceanview Bliss With 360° Views Enjoy the peaceful sound of the waves and a serene, private atmosphere that’s still close to everything. We’re located within walking distance to Philipsburg, the vibrant heart of SXM—Front Street, top shopping, restaurants, and the island’s best casinos. The beach is just 5 minutes away, Step outside to your private patio for sunbathing, and shimmering ocean‑view pool. Villa offers the perfect blend of tranquility and convenience.

LocationFamilyCheckout

A stunning sunset is captured over the calm sea, reflecting vibrant colors onto the water's surface. In the foreground, a serene pool mirrors the sky, enhancing the tranquil ambiance of the outdoor space. The silhouette of trees adds a natural element to the scene.

4.97 out of 5 average rating, 90 reviews

Waterfront "Bonjour" Beacon Hill St Maarten

This stunning 4-bedrooms, 4 bathrooms villa overlooks Maho Bay and provides a front row seat to beautiful SXM sunsets, and over the famous Maho Beach. Enjoy the views while taking a dip in the home’s infinity pool overlooking the ocean or from its multiple outdoor dining and seating options conveniently and securely located minutes from restaurants, bars, nightlife, Maho Market and more, steps away from direct beach access to Simpson Bay Beach. Back up Diesel Generator

LocationValueCleanliness

A modern villa exterior is displayed under a clear blue sky. Sleek white walls are complemented by well-maintained landscaping and palm trees. An outdoor lounge area is visible, featuring comfortable seating and a shaded area for relaxation.

4.87 out of 5 average rating, 86 reviews

Modern 2 bedroom luxury beachside villa with pool

Your own private paradise. Modern 2 bedroom luxury villa in safe gated community with security. New appliances with air conditioning, WIFI, security cameras, and secured free parking including Smart TV with free NetFlix, HBO Max, and Prime access. Private pool with adjacent outdoor dining/lounge area. Perfect for families or couples. Maid and private chef service available if needed. Walking distance from dining, night clubs, and shopping. Steps away from the beach.

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A private pool is situated on a wooden deck, surrounded by lush greenery and palm trees. Sun loungers are positioned nearby, offering a view of the sea and distant boats. The clear water of the pool reflects the vibrant blue sky.

5.0 out of 5 average rating, 109 reviews

VILLA I LOVE VIEW – Luxury villa with sea view

Villa I LOVE VIEW is an oasis of tranquility – with its private pool (naturism possible), large terrace and luxurious kitchen area. Come and discover its view with multiple shades of blue while relaxing on the deckchairs by the pool with zen natural stone reflections Located in Cul de Sac, facing Saint Barth, Pinel Island and the Eastern Bay. Close to the most beautiful beaches of the island, restaurants, water sports, it is the ideal place for your vacation.

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Villa in Upper Prince's Quarter

4.94 out of 5 average rating, 87 reviews

Villa Blue Roc

This luxurious villa is located in a secure residence with a breathtaking view, facing the ocean and the island of St Barthelemy, perched on the heights of Dawn Beach, 15 minutes from the famous beaches/restaurants of Orient Bay and Grand Case in the French part. The villa is also 5 minutes from the Dutch capital, Philipsburg, a must for shopping. Thanks to the large outdoor spaces and the infinity pool, this villa will offer you an unforgettable stay.

ValueFamilySleep quality

A private pool is framed by wooden decking, complemented by two lounge chairs and a side table. A scenic view of azure waters and distant islands is visible, with sailboats dotting the horizon. Lush palm trees provide a tropical ambiance.

4.85 out of 5 average rating, 155 reviews

Villa Bella sea view pool and jacuzzi 3 bedrooms

Wake up every morning facing Pinel Island, in a modern villa bathed in light, with a private pool and a quiet and green environment. The Villa is located in the Horizon Pinel residence overlooking Îlet Pinel, Petite Clef, Orient Bay, Tintamarre and Saint Barthélemy. It overlooks the incredible and famous Cul de Sac Bay Nature Reserve, known for its population of turtles, rays and pelicans. The shallow and always calm bay is ideal for snorkeling

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Villa in Indigo bay, Sint Maarten

A private pool is set in a serene outdoor area, surrounded by lush greenery and palm trees. The pool features a tiled edge, with a wooden tray holding tropical fruits floating in the clear water. A spacious lawn complements the inviting atmosphere.

4.94 out of 5 average rating, 70 reviews

Ocean Dream Villa

Indulge in luxury at a two-bedroom villa in Indigo Bay, Sint Maarten. Enjoy modern elegance, a private pool, and ocean views. Relax indoors or outdoors, savor gourmet meals, and unwind under starlit skies. Luxurious bedrooms offer ocean vistas. Whether for romance or family, this villa promises a memorable Caribbean escape at Ocean Dream, where luxury meets natural beauty. Book now for an extraordinary island retreat.

ValueLocationGetting around

4.77 out of 5 average rating, 149 reviews

Villa in Lowlands

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

Sea View Luxury Villa Perfect for Girls Getaways & Birthday Celebrations Maho Village Celebrate in style at this stunning Sea True villa, custom designed with high end finishes and built for an unforgettable immersive sensorial experience. With 5.8 meter vaulted ceilings a private pool and every amenity you could dream of. It’s the ultimate escape for groups and special occasions.

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4.99 out of 5 average rating, 104 reviews

A panoramic view captures the serene turquoise waters of Great Bay, framed by rolling hills and lush greenery. The horizon features a blend of clouds and sunlight, creating a tranquil coastal atmosphere. Cruise ships are subtly visible along the shoreline.

Villa in Little Bay

Barefoot Villas GreatBay View in Hot Tub & Balcony

Wake up to stunning panoramic views of Philipsburg and Great Bay. Sip your morning coffee as cruise ships glide into port, all while soaking in the refreshing ocean breeze. This centrally located property puts you just minutes away from Philipsburg’s vibrant shopping scene, local supermarkets, restaurants, and some of the island’s best beaches.

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A private outdoor area features a swimming pool surrounded by lounge chairs, with views of the water and distant hills. Palm trees provide shade, while a wooden structure offers a dining space. Natural stone tiles create a welcoming atmosphere, ideal for relaxation.

4.99 out of 5 average rating, 160 reviews

VILLA JADE 2: WATERFRONT SUITE/POOL

VILLA JADE is a complex of 3 villas located in the bay of CUL DE SAC and its islets... VILLA JADE 2 is a spacious/sea view suite for 2 people on the water, with a private pool. The 3 villas are adjoining but very quiet and private. Your unique view is the sea... Direct access to the sea via a pontoon, and kayaks at your disposal.

ValueFamilyParking

4.91 out of 5 average rating, 32 reviews

A spacious living area is highlighted by large glass doors, allowing natural light to fill the room and offering unobstructed ocean views. Comfortable white sofas complement a wooden coffee table, while vibrant artwork adds a pop of color to the decor. The inviting atmosphere is enhanced by the lush surroundings visible through the windows.

Villa in Sint Maarten

Sea view 3BR Spring Sea Villa w/ pool, St Maarten

The luxurious Villa Spring Sea will offer you all the comforts for an unforgettable holiday in a dream setting: fully equipped modern kitchen open to living room and its huge terraces, 3 large bedrooms with their own bathroom, detached villa, private pool, exceptional sea view, 5 min walk to Indigo Bay beach.

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Popular amenities for Simpson Bay villa rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

An infinity pool is visible in the foreground, its clear water merging with the expansive blue sea. Beyond, the horizon features distant islands under a clear sky, complemented by palm trees swaying gently in the breeze.

4.83 out of 5 average rating, 90 reviews

Villa Indigo Dream, Indigo Bay SXM

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5.0 out of 5 average rating, 8 reviews

Seabreeze beachfront 3bedroom on Simpsonbay beach

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4.81 out of 5 average rating, 16 reviews

Villa in Indigo Bay

AZUR 4BR 4.5BA Walk to Indigo Beach- Sea Side Dr.

LocationNearbyView

5.0 out of 5 average rating, 18 reviews

An outdoor seating area features a black wicker sofa with colorful cushions. Nearby, a private pool glistens under the sun, surrounded by lush greenery. The terrace's wooden flooring leads to steps down to the pool, offering a relaxing space to enjoy the warm weather.

Villa in Koolbaai

Sol y Mar - Beachfront Penthouse with private pool

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4.93 out of 5 average rating, 29 reviews

Villa in Oyster Pond

Villa Kyanéa | Ocean View St. Barth · Private Pool

LocationFamilyComfort

5.0 out of 5 average rating, 34 reviews

The villa features a modern design with two levels, surrounded by lush greenery. An infinity pool is situated in front, with reclining chairs positioned nearby. The outdoor dining area is visible, and the expansive glass windows reflect the vibrant surroundings, inviting natural light into the space.

Villa in Indigo Bay

Life's Good

ValueLocationCleanliness

4.8 out of 5 average rating, 54 reviews

A stunning view features a vibrant infinity pool that blends into the serene landscape. Lush tropical plants surround the area, and a hillside is visible in the background, highlighting the villa's connection to its natural surroundings.

Villa in Cole Bay

SeaSoleil LuxuryVilla With Private Pool IndigoBay

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Villa in Les Terres Basses

A private pool with turquoise water is surrounded by a spacious wooden deck featuring several lounge chairs. Lush greenery frames the area, and the ocean is visible in the distance under a clear blue sky.

4.88 out of 5 average rating, 24 reviews

Private villa / beautiful View next to La Samanna

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Luxury villa rentals

An infinity pool extends toward the horizon, creating a seamless view of Orient Bay and its surrounding islands. Comfortable lounge chairs with orange accents are positioned nearby, offering relaxation against a backdrop of vibrant greenery and a clear blue sky.

4.97 out of 5 average rating, 69 reviews

Private Orient Bay Villa with Spectacular Views

LocationFamilyCheckout

5.0 out of 5 average rating, 14 reviews

Villa in Mont choisy

Sunset View – Steps from Friar’s & Happy Bay

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Villa in Upper Prince's Quarter

4.92 out of 5 average rating, 25 reviews

Villa Marant - Elegant Luxury Caribbean Escape

ValueFamilyNearby

4.68 out of 5 average rating, 44 reviews

A sleek, reflective pool extends towards the horizon, capturing the vibrant sunset. Lush greenery frames the view, adding a natural element to the scene. The setting creates a peaceful ambiance, inviting relaxation amidst the beauty of the surrounding landscape.

Villa in Cole Bay

A heavenly Sint Maarten's retreat

LocationFamilyCheckout

An open living area reveals wooden beams overhead and large glass doors that connect to the outdoor space. A light-colored sofa rests on polished wood flooring, accompanied by a coffee table. The serene view of greenery and ocean is visible through the doors.

5.0 out of 5 average rating, 48 reviews

Water access, snorkeling gear & kayaks

LocationFamilyHospitality

5.0 out of 5 average rating, 36 reviews

Villa Pure • 3BR waterfront with kayaks, Wi-Fi, AC

LocationFamilyBarbecue

4.91 out of 5 average rating, 11 reviews

A private pool is framed by a spacious wooden deck, featuring several lounge chairs and umbrellas for shade. Lush palm trees surround the area, with a clear view of the ocean in the background, complemented by a bright blue sky and gentle clouds.

Villa in Marigot

NEW Les Terres Basses - Villa Coco Paillette - Sxm

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Villa in Upper Prince's Quarter

An inviting outdoor terrace showcases a comfortable seating area with black wicker furniture, set against the backdrop of a sparkling infinity pool. The ocean horizon stretches beyond, while lush greenery and bright skies add to the serene atmosphere.

4.9 out of 5 average rating, 21 reviews

Luxe 3BR Villa: Pool & Sweeping Ocean Views

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Villa rentals with a pool

A clear blue pool is depicted surrounded by light-colored tiles. Lounge chairs are positioned beside the water, and a potted plant adds greenery to the space. The villa's walls are painted in a soft blue, and sunlight reflects off the water's surface.

4.67 out of 5 average rating, 54 reviews

Villa Sunset : very close to two beaches !

ValueLocationWi-Fi

4.9 out of 5 average rating, 40 reviews

Little Paradise 2, private pool, beautiful view

ValueFamilyHospitality

5.0 out of 5 average rating, 17 reviews

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.

Villa in Dawn Beach

Ocean Pearl - Spacious Villa in Dawn Beach

LocationValueHospitality

5.0 out of 5 average rating, 17 reviews

Villa Koala, heated pool, sea view, Cul de Sac

FamilyValueLaundry

4.97 out of 5 average rating, 33 reviews

A spacious balcony offers a circular wooden dining table surrounded by four red cushioned chairs, with panoramic views of the ocean and nearby coastline. Bright skies and distant land features enhance the serene outdoor setting, providing an inviting space to enjoy meals or relaxation.

Villa in Pelican Key

Villa Sea Forever @ Pelican Key - Paradise Awaits!

LocationValueQuiet

A serene pool area is surrounded by a wooden deck, featuring sun loungers. The turquoise water of the pool reflects the bright blue sky, scattered with white clouds. Lush greenery and palm trees frame the scene, providing a tranquil atmosphere.

4.95 out of 5 average rating, 79 reviews

Slowlife Harmony - Caribbean Villa Three Bedrooms!

ValueLocationPool

Soft cushions in neutral tones are arranged on a stone ledge, overlooking a heart-shaped pool. Lush greenery surrounds the outdoor area, with patio umbrellas providing shade and sunlight filtering through the clouds. A spacious living area is visible in the background.

5.0 out of 5 average rating, 25 reviews

Villa Véronica - Orient Bay

LocationFamilyIndoor spaces

A bright living area is highlighted by a light-colored sofa adorned with blue cushions. Large glass doors provide a view of the beach and outdoor seating, while unique wooden side tables complement the decor. Natural light fills the space, enhancing the serene atmosphere.