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Villa vacation rentals in Simpson Bay

Find and book unique villas on Airbnb

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$37,631 GYD per night before taxes and fees

  • Verified guest reviews

    Over 560 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 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!

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 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.

ValueLocationView

4.95 out of 5 average rating, 81 reviews
Luxe
An inviting infinity pool reflects the clear blue sky and ocean, creating a seamless horizon. A floating tray with refreshments is positioned in the water, while a contemporary chair is seen at the pool's edge, enhancing the tranquil atmosphere.
Villa

Ocean Breeze B

Welcome to unparalleled luxury at Indigo Bay, Sint Maarten. Nestled in one of the island's most sought-after gated communities, this 3-bedroom villa offers modern elegance with breathtaking views of the Caribbean Sea. The villa is thoughtfully designed with an expansive living room, full kitchen, bar, and a TV room for relaxation. Step outside to your private oasis featuring a private pool, BBQ area, and sun-soaked deck, perfect for alfresco dining or unwinding with a cocktail. The master suite

LocationValueDecor

5.0 out of 5 average rating, 16 reviews
Guest favorite
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.
Villa

VILLA I LOVE VIEW - villa luxe avec vue mer

Villa I LOVE VIEW est une oasis de tranquillité – avec sa piscine privative (naturisme possible), sa grande terrasse et son espace de cuisine luxueux. Venez découvrir sa vue aux multiples nuances de bleues en vous relaxant sur les transats au bord de la piscine aux reflets pierres naturelles zen Située à Cul de Sac, face à Saint Barth , l'ilet Pinel et la Baie Orientale. A proximité des plus belles plages de l'ile, restaurants, divertissements nautiques, c'est le lieu idéal pour vos vacances.

LocationFamilyLong stay

5.0 out of 5 average rating, 110 reviews
Superhost
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

Villa Bella vue mer piscine et jacuzzi 3 chambres

Réveillez-vous chaque matin face à l’île Pinel, dans une villa moderne baignée de lumière, avec piscine privée et un environnement calme et verdoyant. La Villa est située dans la residence Horizon Pinel vue sur îlet Pinel, petite Clef, Orient Bay, Tintamarre et Saint Barthélemy. Elle donne vue sur l'incroyable et célèbre réserve naturelle de la baie de Cul de Sac, connue pour sa population de tortues, raies et pélicans. La baie peu profonde et toujours calme est idéale pour le snorkeling

ValueLocationLong stay

4.85 out of 5 average rating, 157 reviews
Top guest favorite
Villa in Upper Prince's Quarter

Villa Blue Roc

Cette villa luxueuse , est situee dans une residence securisee avec une vue epoustouflante , face a l ocean et l ile de St Barthelemy, Perchee sur les hauteurs de Dawn Beach, a 15 minutes des fameuses plages/restaurants d Orient Bay et Grand Case en partie francaise. La villa est egalement a 5 minutes de la capital hollandaise , Philipsburg, un incontournable du shopping. Grace aux grands espaces exterieurs et a la piscine a debordement , cette villa vous offrira un sejour inoubliable.

FamilyValueQuiet

4.94 out of 5 average rating, 88 reviews
Top 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

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

LocationFamilyGetting around

4.97 out of 5 average rating, 92 reviews
Guest favorite
A dining area is set outdoors under a ceiling fan, featuring a round table with floral-patterned plates. Surrounding lounges provide comfortable seating, with a barbecue grill in view. Vibrant ocean views stretch beyond, framed by the villa's modern architecture.
Villa in Indigo Bay

SeaBreeze Luxury Villa Pool & Hot Tub Indigo Bay

The SeaBreeze Villa combines modern architectural design with expansive views of the sky at Indigo Bay, the top-tier gated community in St. Maarten. With four bedrooms and a convenient location just a brief stroll from the beach, this residence features sliding glass walls that lead to a spacious sun terrace and a private pool with stunning vistas of the Caribbean Sea. Offering all the amenities for luxurious island living, The Villa epitomizes upscale coastal lifestyle.

LocationFamilyQuiet

4.91 out of 5 average rating, 87 reviews
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

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.

ValueLocationDecor

4.87 out of 5 average rating, 89 reviews
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

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.

LocationValueWalkability

4.93 out of 5 average rating, 73 reviews
Top guest favorite
A serene infinity pool extends to the horizon, bordered by smooth stone tiles. Three light blue loungers are positioned for relaxation, overlooking the expansive sea and a clear blue sky scattered with clouds.
Villa in Beacon Hill

Infinity Ocean Edge - Luxury Oceanfront Penthouse

✨ Infinity at Ocean Edge with IRE Vacations✨ Come take advantage of this luxury property located on the end of the Beacon Hill peninsula, ensconced on all sides by the inviting Caribbean Sea! This spectacular waterfront property is one of a kind. Located just minutes from several of St. Maarten’s most popular beaches and beach bar hangouts, a great day is always guaranteed. This property is not kid friendly.

ValueLocationBathroom

5.0 out of 5 average rating, 27 reviews
Guest favorite
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.

ValueFamilyBeach

4.77 out of 5 average rating, 154 reviews
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

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.

LocationValueLayout

4.98 out of 5 average rating, 47 reviews

Popular amenities for Simpson Bay villa rentals

When is the best time to visit Simpson Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$419,372 GYDG$322,996 GYDG$322,996 GYDG$277,630 GYDG$245,226 GYDG$248,362 GYDG$255,052 GYDG$237,909 GYDG$237,909 GYDG$237,909 GYDG$237,909 GYDG$338,675 GYD
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