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.

0 of 0 items showing

1 of 3 pages

Guest favorite

Villa in Cul-de-Sac

4.97 out of 5 average rating, 38 reviews

Spacious Villa - Saint Martin - Pool/4 Bedrooms

Discover your Spacious Villa BNB – contemporary island vibes and stunning views, designed just for you. Its airy open-plan layout and four sunlit bedrooms, this retreat is a symphony of comfort. Immerse yourself in the experience – sip wine by the private pool or relax in the gazebo with ocean views. No water worries here; our cistern guarantees a seamless supply. Your family's vacation dreams await. Book now to secure your spot in this haven of tranquility and luxury! Can't wait to welcome you.

Guest favorite

Villa in Oyster Pond

4.93 out of 5 average rating, 40 reviews

Ultra Modern Tropical Villa with backup generator

Villa Helios overlooks the Ocean with 210 degree views, including St. Barts. Views from every room. Private and secure, the villa is suitable for an extended family or three/four couples - rooms are well separated. The wind provides a steady cooling breeze on the Atlantic side of the island. Open the sliding door in the morning and enjoy the topical breeze all day. Located on the prestigious quiet peaceful Plateau, a small gated community of 6 homes. Includes backup Diesel generator

Superhost

Villa in Lowlands

4.91 out of 5 average rating, 46 reviews

Villa Sonrisa, Beachfront and stunning ocean view

As the plane lands in St. Martin, your soul lifts. To preserve that feeling, where you stay is important. Look no further because you have found your dream vacation destination. Villa Sonrisa is a 2400 sq. ft. (250 sq. m), two-level villa located in Cupecoy. The main living space is on the first floor, both bedrooms with ensuite baths are on the second. This VERY private villa is perched on a bluff overlooking Cupecoy Beach. Enjoy an unobstructed panorama of the islands of Saba, Statia, and St

Superhost

Villa in Upper Prince's Quarter

4.88 out of 5 average rating, 34 reviews

Villa Mila | The Pearl of Oyster Bay | St. Maarten

Experience refined luxury at the newly transformed Villa Mila Estate – an avant-garde masterpiece with 5 lavish beds and 5.5 baths. Overlooking serene Oyster Pond in Sint Maarten, it invites with breathtaking ocean panoramas. Relax by the hillside infinity pool, where sailboats and St. Barths grace the backdrop. Elevate at Villa Mila Estate – where opulence and sophistication intertwine. Each corner exudes indulgence. Your desires become reality, etching every moment into exquisite memory.

Guest favorite

Villa in Upper Prince's Quarter

4.9 out of 5 average rating, 39 reviews

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.

Guest favorite

Villa in Cay Bay

4.99 out of 5 average rating, 67 reviews

Make your dream come true!

Overlooking the private beach of Indigo Bay, Villa Olisa is in a tropical environment with spectacular sea view; it offers a private swimming pool, marble terrace, trendy outdoor living room, outdoor dining room on the sea, equipped with a power BBQ, large indoor dining room, a large super-equipped kitchen (where you can show off your talents as a chef), 3 bedrooms with 2 Queen beds and a King bed, 2 large bathrooms with glass showers, an outdoor toilet and shower on the pool.

Guest favorite

Villa in Collectivity of Saint Martin

5 out of 5 average rating, 56 reviews

VILLA I LOVE VIEW - Luxury Villa with Sea View

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

Guest favorite

Villa in Upper Prince's Quarter

5 out of 5 average rating, 44 reviews

EXQUISITE 5-STAR BEACHFRONT VILLA

Guaranteed to create a 5-Star experience! Fully air-conditioned 3 BR, 3 1/2 bath Beachfront Villa w/private pool. If you love the ocean & spectacular views, but fine living & comfort are important to you, we have it all! My home offers Personal housekeeper, Private Chef for hire, full Concierge Service, private garage, and gym. Also, food and groceries delivered prior to your arrival, access to all the services and amenities next door at the Oyster Bay Hotel.

Superhost

Villa in Orient Bay

4.82 out of 5 average rating, 67 reviews

Villa Allamanda, sublime view, heated hot tub

Villa Allamanda is a very spacious house located in the secure Parc de la Baie Orientale, French side. It offers many assets for holidays for families or groups of friends: * Large terrace with pool, and its HEATED and overflowing JACUZZI * Spectacular view of the bay and surrounding islands * Beach, water activities and shops within a 10-minute walk * 4 bedrooms with private bathrooms * Bluetooth speakers around the pool, with USB charger * Wifi

Guest favorite

Villa in MF

4.96 out of 5 average rating, 54 reviews

Private Orient Bay Villa with Spectacular Views

Villa La Sarabande can be your perfect Caribbean getaway! This villa offers a stylish setting and fabulous 180° panoramic views of Orient Bay. A wonderfully secluded hillside location within the upscale villa neighborhood of the Orient Bay gated community, paired with many luxury amenities and services, make this fine property the perfect place to enjoy your Caribbean vacation in elegance, style and total relaxation.

Guest favorite

Villa in Collectivité de Saint-Martin

4.94 out of 5 average rating, 51 reviews

Slowlife Harmony - Caribbean Villa Three Bedrooms!

Harmony is your perfect vacation home, will give you the feeling of being at home in the Caribbean, this spacious 3-bedroom Caribbean style villa, we can accommodate a family, couples and friends. Harmony will be your home away from home, and at the same time you will have a personalized service for requests and to guide you with information about all the activities and places that you must experience on our island.

Guest favorite

Villa in Cul-de-Sac

4.96 out of 5 average rating, 45 reviews

Villa Atao, sublime view of Orient Bay and the islands

Villa Atao is a gorgeous vacation home with 180° ocean views featuring 4 bedrooms and 4 bathrooms, close to Orient Bay. Villa Atao has many assets for a relaxing holiday with family or friends. * Large living spaces * Private pool * Air conditioning in all rooms, * Secure residence with camera * Wifi 100 Mbps * Villa completely renovated in 2020