Upside

Pointe Milou

3 bedrooms

3 bathrooms

From $6,000 P/W

Chic and contemporary with top-notch views

As the name suggests, there is very little downside to the contemporary Villa Upside (UPS). The luxury rental property was designed to have vast ocean views, and a recent renovation gives it an easy St. Barth style of living and all the conveniences one could hope for in an island vacation home.

A highlight of Villa Upside is its panoramic views. The main social area contains an open-plan living room and good-size kitchen that are laid out to let guests gaze out over the Caribbean at every turn. A breakfast bar makes the space more versatile. The living area and kitchen also extend seamlessly onto the wraparound terrace, which has a covered dining table with eight seats and a grill nearby. Its swimming pool is easily accessible and has an infinity edge to blend with the sea below.

With its location in Pointe Milou, the villa also has a view of Lorient Bay and the small islands of Île Toc Vers, Île Fregate, and Île Bonhomme. It is just above the Christopher Hotel, a short drive from the beaches in Lorient and Marigot, and an easy drive to the shops and restaurants in St. Jean. Gustavia is a 20-minute drive away.

Villa Upside is spread over two floors, which are decorated in a chic style with pops of color. The indoor-outdoor public areas are on the upper level, along with one of the bedrooms, which has floor-to-ceiling windows on two of the walls to maximize the water views.

An internal staircase takes you down to the two additional bedrooms below, or these also have direct access from outside. They are equal in size, and one of them has two twin beds that can be converted into a king. Like the upstairs bedroom, each one has an ensuite bathroom and a television.

All of this makes Villa Upside well suited for a variety of groups. And of course, the Sibarth Concierge can customize activities to make a stay memorable for any type of traveler – or simply streamline things by pre-stocking the refrigerator or booking a babysitter.

Sibarth Bespoke Villa Rentals is proud to offer the elegance and views of Villa Upside.

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1 bedroom

2 bedrooms

3 bedrooms

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Summer Season (2026)

Apr 15 – Dec 14, 2026

1 bedroom$6,000 P/W
2 bedrooms$7,000 P/W
3 bedrooms$8,000 P/W

Holiday Season (2026)

3 bedrooms$22,500 P/W

High Season (2027)

Dec 15, 2026 – Apr 14, 2027

1 bedroom$8,000 P/W
2 bedrooms$9,000 P/W
3 bedrooms$10,000 P/W

Summer Season (2027)

Apr 15 – Dec 14, 2027

1 bedroom$6,000 P/W
2 bedrooms$7,000 P/W
3 bedrooms$8,000 P/W

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Rate doesn’t include 5% tourism tax and 10% service fee.

Services included with every booking

Reservation assistance

We’re here at every step, even before you book. Share your dates and wishes, and our reservations team will help you find the villas that fit.

Concierge services

Every booking includes a dedicated concierge; your on-island insider before and during your stay. From dinner reservations to yoga at sunrise, we’ll do our best to arrange it.

Travel support

From arrival to departure, we’re here to guide you. From your first steps on the island to your final farewell, we’ll take care of the details.

Welcome gift

When you book directly with us, each villa is prepared with a thoughtful welcome gift. Wine, snacks, and a few extra touches to begin your stay the right way: laid back.

Daily housekeeping

Our daily housekeeping service keeps your villa fresh and tidy, leaving you free to swim, explore, relax, and truly switch off. Provided every day except Sundays and holidays.