Villa Upside St Barts

Upside is a contemporary villa. Its design is clean, bright, and focused entirely on the horizon. Vaulted ceilings with exposed dark beams stretch overhead, while a palette of crisp white and earthy tones forms a calm, neutral backdrop.

Vibrant color is used strategically. Lime green cushions, turquoise throws, and yellow accents pop against the serene base. This isn’t just decoration; it’s a deliberate energy that mirrors the tropical setting outside. The visual vibe is airy and modern, a space where every material and texture, from smooth dark wood floors to woven pendant lights, feels considered. The architecture serves a single purpose: to frame the panoramic ocean view from Lorient Bay out to the islands of Île Toc Vers, Île Fregate, and Île Bonhomme. This is the villa’s defining feature, confirmed across every source and evident in every room. Spaces here flow with an intuitive ease. You enter on the main upper level into a single, open-plan great room that combines living, dining, and kitchen functions. Large, statement woven pendant lights hang above a comfortable seating area arranged to face the view. A rustic wooden ladder leans against a wall as a decorative touch, and a Pioneer speaker stands ready for your playlist.

The room’s genius is its transparency. Floor-to-ceiling glass doors line the entire sea-facing wall, dissolving the boundary between inside and out. They open fully onto the wraparound terrace, pulling the Caribbean breeze and the sight of the infinity pool right into the living space. Across the room, the kitchen is well-equipped for preparing meals, with a breakfast bar adding a casual dining option. It includes a microwave, a coffee machine, an espresso machine, a toaster, a blender, and a dishwasher, plus a noted Nespresso machine. A mosquito net is also provided. This kitchen doesn’t turn its back on the action; it opens directly to the pool area, so the cook never loses the view or the conversation. The three bedrooms at Upside are all oriented toward the ocean, and each is an ensuite sanctuary with air conditioning, a safe, and a TV. The layout provides a welcome sense of separation, with the primary suite enjoying the upper level and the two guest rooms situated privately below.

Bedroom 1 is the master suite on the main floor. It’s anchored by a king-sized bed (6.56 × 6.56 feet) and its most striking feature is the wall of glass granting direct access to the terrace. You wake up to the same panoramic seascape as the living room. The room is equipped with both French and US satellite TV, a DVD player, and notably, a 3D TV. Its ensuite bathroom is fitted with a shower. This suite feels integrated with the villa’s social flow yet remains a private retreat just steps from the pool. Descend via the internal staircase, and you find the two lower-level bedrooms. They offer a quieter, more secluded atmosphere while maintaining that essential ocean view. Bedroom 2 features a queen-sized bed (5.91 × 6.56 feet) and is equipped with US satellite television. Its ensuite bathroom also has a shower. Bedroom 3 mirrors this setup exactly, with another queen-sized bed and the same suite of amenities including US satellite TV and a shower ensuite.

The equality in size and furnishings makes these rooms ideal for couples or friends traveling together, and their location on the lower floor ensures privacy from the main living area. Both rooms also have independent outside access, offering flexibility for coming and going. Outdoor living is the true centerpiece of this Pointe Milou villa. The wraparound terrace creates a series of perfect settings for every part of the day. The infinity pool, measuring 11.5 by 16.4 feet, is the visual anchor. With a glass railing on its far edge, it creates a suspended effect where the water appears to spill into the sea below. It’s not heated, but in this climate, it rarely needs to be. Sun loungers are positioned for all-day basking with that uninterrupted vista. Just off the kitchen, a gas barbecue is set up for island-style cookouts. This area becomes a secondary lounge spot, perfect for grilling fresh fish as the sky changes color.

Under a covered pergola, a rectangular wooden dining table with woven placemats is set for eight, providing an elegant, shaded spot for long meals. The space is equipped with Wi-Fi, so you can stream music to the outdoor areas, and an iron and ironing board are available inside for any needed touch-ups. From sunrise coffee to sunset cocktails, every moment outdoors is accompanied by that commanding view of Lorient Bay and the promise of exceptional evening sunsets. Location defines the Upside experience. Perched in the hills of Pointe Milou, the villa is just above the iconic Christopher Hotel, whose pool club, restaurant, and spa are within walking distance. The setting offers both elevated privacy and remarkable convenience. Direct beach access is available, putting the sand and sea within your reach. The popular sands of Lorient Bay are roughly a five-minute drive, while the quieter Marigot Bay is about the same distance in the other direction.

For provisions and dining, the shops and restaurants of St. Jean are only ten minutes away by car. Gustavia, the island’s capital, is about a twenty-minute drive. The airport is a convenient ten to twenty minutes from the villa, and a 4x4 vehicle is not required for access.

This is a mid-range three-bedroom villa in Pointe Milou that cleverly balances a private escape with easy connectivity to the best of St. Barts. Booking Upside through Premium Island Vacations means you’re supported by two decades of on-island expertise.

We handle the details, from initial inquiry to arranging any concierge services you might desire during your stay. Our team knows this villa and this area intimately, ensuring your time in this contemporary St. Barts villa is as seamless and memorable as the view from its terrace.