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Villa holiday rentals in Simpson Bay

Find and book unique villas on Airbnb

Quick stats about villa rentals in Simpson Bay

  • Total holiday rentals

    Explore 30 holiday rentals in Simpson Bay

  • Nightly prices starting at

    Simpson Bay holiday rentals start at £133 per night before taxes and fees

  • Verified guest reviews

    Over 560 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    30 properties feature pools

  • Wifi availability

    30 of Simpson Bay holiday rentals include wifi 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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Luxe
Villa in Cole Bay
5 out of 5 average rating, 8 reviews

Las Brisas Penthouse A

Welcome to this stunning 3-bedroom penthouse located in the prestigious gated community of Las Brisas, Cole Bay, St. Maarten. This luxurious residence offers an unmatched living experience with breathtaking views and modern amenities. The penthouse features three spacious bedrooms, each designed with elegance and comfort in mind. The master suite boasts an en-suite bathroom and private balcony, perfect for soaking in the serene surroundings. The open-concept living and dining areas flow seamles

Guest favourite
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
4.95 out of 5 average rating, 78 reviews

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.

Guest favourite
A serene pool reflects the vibrant colors of a sunset, with bougainvillea blossoms floating gently on the water's surface. Lush green foliage frames the view, creating a peaceful atmosphere that invites relaxation.
Villa in Simpson Bay
4.97 out of 5 average rating, 86 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, 84 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 favourite
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
5 out of 5 average rating, 105 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.

Top guest favourite
Villa in Upper Prince's Quarter
4.94 out of 5 average rating, 86 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.

Guest favourite
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
4.85 out of 5 average rating, 150 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 favourite
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
4.95 out of 5 average rating, 64 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.

Top guest favourite
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
5 out of 5 average rating, 24 reviews

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.

Top guest favourite
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
4.99 out of 5 average rating, 98 reviews

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.

Top guest favourite
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.
Villa in Cul-de-Sac
4.99 out of 5 average rating, 156 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.

Guest favourite
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
4.92 out of 5 average rating, 26 reviews

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.

Popular amenities for villa rentals in Simpson Bay

When is the best time to visit Simpson Bay?

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Avg. price£1,482£1,141£1,141£993£901£901£901£841£841£841£841£1,196
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