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Villa vacation rentals in Simpson Bay

Find and book unique villas on Airbnb

Top-rated villa rentals in Simpson Bay

Guests agree: these villas are highly rated for location, cleanliness, and more.

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Guest favorite
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
5 out of 5 average rating, 31 reviews

Villa Sea Forever @ Pelican Key - Paradise Awaits!

Experience a piece of paradise at "Villa Sea Forever" in Pelican Key, Simpson Bay, Sint Maarten! This top floor, 2-bedroom, 2.5-bathroom haven offers mesmerizing, panoramic ocean & sunset views. Dive into pure bliss with a pool, gated community, private parking space, and all the comforts you need, including a full size washer & dryer, and fully stocked kitchen. Feel the breeze from your huge double balcony. Your dream escape awaits at "Villa Sea Forever" where breathtaking moments are endless!

Guest favorite
Villa in Collectivité de Saint-Martin
5 out of 5 average rating, 5 reviews

Villa Litchi | Collection Villas Saint-Martin

Cette villa de 2 chambres entièrement rénovée, au design moderne et rafraîchissant, est désormais disponible. Admirez les couchers de soleil spectaculaires sur la mer des Caraïbes depuis la terrasse ou le salon. Parfaite pour un couple ou une petite famille, elle offre également la possibilité de se connecter avec la Villa Kiwi grâce à son jardin communicant. Ainsi, 2 familles ou groupes d’amis peuvent partager des moments mémorables tout en profitant pleinement des équipements de ces 2 villas.

Top guest favorite
An open-concept living space features large sliding glass doors that reveal views of the tranquil bay. A dining area with a wooden table and upholstered chairs sits centrally, complemented by a cozy sofa adorned with colorful throw pillows. A vibrant platter of fresh fruit and charcuterie adds a decorative touch.
Villa in Indigo Bay
4.96 out of 5 average rating, 25 reviews

Villa Solandra – 3BR Oceanfront Sunset w/ Pool

Welcome to Villa Solandra, a western facing ocean front luxury 3BR/3BA home with a private pool in Indigo Bay. Enjoy romantic & epic sunsets, this cliffside escape blends indoor-outdoor living with sweeping Sea & Bay views, two large oceanfront balconies, and designer interiors. Enjoy a chef inspired kitchen, luxury king suites w/ ensuite baths, private garden just minutes from beaches, dining, Simpson Bay and Maho’s iconic plane spotting. Perfect for families, friends, or romantic getaways.

Guest favorite
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.
Villa in Simpson Bay
4.96 out of 5 average rating, 80 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

Superhost
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.
Villa in Simpson Bay
4.87 out of 5 average rating, 69 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.

Guest favorite
An aerial view of the villa showcases its modern architecture with a terracotta-tiled roof and expansive outdoor spaces. A large infinity pool reflects the surroundings, while shaded areas with loungers and a fire pit area provide spaces for relaxation and gathering.
Villa in Upper Prince's Quarter
4.95 out of 5 average rating, 114 reviews

The Blue Door Villa - 4 bed ocean view home

At the Blue Door Villa, we offer our guests all the creature comforts of being in a well-equipped vacation home. We are located on the Dutch side, minutes from the French border in a quiet gated community. The Blue Door Villa is a perfect place to relax while you listen to ocean waves and swim in the infinity pool. There are multiple outdoor spaces offering privacy or space to gather. We are now offering our guests an exclusive, free concierge service.

Top guest favorite
A patio area is visible, featuring a private pool beside comfortable loungers, adorned with orange towels. A shaded dining space with a table is positioned near the water's edge, with picturesque views of the bay and surrounding landscape.
Villa in Cul-de-Sac
4.99 out of 5 average rating, 165 reviews

VILLA JADE 1: FEET IN THE WATER/POOL SUITE

VILLA JADE is located in the bay of "FRENCH CUL DE SAC". It is a beachfront complex consisting of 3 private villas. VILLA JADE 1 is a suite for 2 people with a private pool. The villas are quiet and private... your only view is the sea. The bay of "FRENCH CUL DE SAC" is 5 minutes from ORIENT BAY, touristy with restaurants, bars, water activities, but also a few minutes from GRAND CASE, our typical little village with gourmet restaurants by the sea....

Guest favorite
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.
Villa in Cul-de-Sac
4.84 out of 5 average rating, 133 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

Guest favorite
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.
Villa in Indigo bay, Sint Maarten
4.97 out of 5 average rating, 39 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.

Guest favorite
Villa in Lowlands
4.75 out of 5 average rating, 130 reviews

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.

Guest favorite
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 Cole Bay
5 out of 5 average rating, 13 reviews

Sol y Mar - Beachfront Penthouse with private pool

✨ Sol y Mar with IRE Vacations ✨ Beautiful beach penthouse Sol Y Mar is located in the heart of Simpson Bay. Sol Y Mar is steps away from the popular Kimsha beach, as well as many restaurants and activities of the area. This beach penthouse sits in the midst of it all. Ideal if you are looking to be within walking distance to supermarkets, restaurants, bars, clubs & watersports.

Top guest favorite
An infinity pool with crystal-clear water extends alongside the terrace, offering views of the lagoon and surrounding landscape. Palm trees and sun loungers can be seen at the water's edge, with blue skies and fluffy clouds reflecting on the water's surface.
Villa in Les Terres Basses
5 out of 5 average rating, 33 reviews

Brand new! - Slowlife - Enjoy Villa

Completely NEW Villa!! Enjoy is a beautiful house that we «placed» on the sand. Thinking on every detail for your greatest comfort, you will appreciate its unique location, an exceptional interior design, and its extraordinary outdoor spaces. In the very exclusive and secure residence of Terre Basses, very close to the beach of Baie Longue, experience an incomparable holiday.

Popular amenities for Simpson Bay villa rentals

When is the best time to visit Simpson Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$358,631 GYDG$358,631 GYDG$343,575 GYDG$281,259 GYDG$255,120 GYDG$255,120 GYDG$255,120 GYDG$237,972 GYDG$237,972 GYDG$237,972 GYDG$237,972 GYDG$358,631 GYD
Avg. temp26°C26°C26°C27°C28°C29°C29°C29°C29°C29°C28°C27°C

Quick stats about villa rentals in Simpson Bay

  • Total vacation rentals

    Explore 30 vacation rentals in Simpson Bay

  • Nightly prices starting at

    Simpson Bay vacation rentals start at G$52,279 GYD per night before taxes and fees

  • Verified guest reviews

    Over 460 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Wi-Fi availability

    30 of Simpson Bay vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Simpson Bay rentals

  • 4.8 Average rating

    Simpson Bay stays are highly rated by guests—averaging 4.8 out of 5!