Hosted Villas
Inspirations
Contact Information: 1-800-374-6637
Experience contemporary Caribbean elegance at Villa Upside, a luxury St. Barth’s villa rental set on the scenic hills of Pointe Milou. Designed to capture sweeping ocean views from every angle, this three-bedroom villa combines modern sophistication with effortless island living. The open-concept main level features floor-to-ceiling windows, a fully equipped gourmet kitchen, and an airy living area that opens onto a sun-drenched terrace. Outside, a dramatic infinity pool appears to float above the turquoise horizon—perfect for a morning swim or sunset cocktail. Each of the three ensuite bedrooms offers privacy, comfort, and refined décor, creating an inviting sanctuary for families or small groups. Alfresco dining, shaded lounging areas, and soft evening breezes complete the relaxed, luxurious atmosphere. Ideally located just five minutes from Lorient Beach and a short drive to St. Jean’s boutiques and restaurants, Villa Upside is the ultimate Caribbean hillside retreat—where panoramic views, thoughtful design, and the charm of St. Barth’s come together in perfect harmony.
The corals – filled with lots of small, colourful reef fish – here are definitely worth seeing up-close. The most spectacular dives are around Pain de Sucre, an islet off Gustavia harbour, and around l’Ane Rouge, a small cape off Colombier Bay.
From casual beachfront eateries to upscale establishments, the dining scene here is superb. Check out the freshly renovated Latin-French restaurant, Bonito or opt for Italian at the world-renowned restaurant, L'Isola.
One of the best things about being on an island is the opportunity to eat really fresh fish. A great place to watch local fisherman, and buy your entrée for the night, is the Fish Market in Gustavia. Get there early for the best selection.
A local fave is Saline Beach, which is deep and long tends to be quiet (there are no resorts directly on the beach). Colombier Beach is the most famous and one of the best places to watch the sunset; while Gouverneur Beach is a must visit.
Located at La Pointe on Gustavia Harbor in a recently restored historic building that dates back to the island’s Swedish period (1785-1878), it features artifacts and pictorial documents from St. Barths’ past.
St. Jean and Lorient are great for kids. St. Jean has 2 beaches to choose from, one where older kids can try out windsurfing and other that is calm and sheltered; while Lorient has magnificent natural pools that are great for little ones to swim in.
At the lagoon in Grand Cul-de-Sac, kids as young as 5 can get out in a kayak with a transparent bottom to take a look at sea turtles and the fauna in the seabed, while older kids can try out kite-surfing.
Play with friends or take a private lesson with the professional coaches at the St. Barth Tennis Club.
Built in 1787 by the Swedish as one of 3 forts to protect the harbour, it offers amazing panoramic views of Gustavia and the harbour. There is also the remains of a lighthouse and a couple of fiberglass cannons.
In order to kick-start the planning process, it would help us immensely if you could provide us with your contact details and answer a couple of quick questions about your travel plans. Please fill out and submit this form and we will be in touch shortly, or engage us in a live chat.If you would prefer to speak to someone by phone during regular business hours, please call us at 1-800-374-6637 and one of our Experience Managers will be happy to assist you.
For all other general inquiries, please email us at
info@hostedvillas.com
