Perched high on the hillside of Pointe Milou, Villa Upside blends sleek contemporary design with sweeping Caribbean panoramas. With three king suites, a luminous great room, and an iconic pool suspended above the sea, it is one of the most stylish St Barthelemy vacation rentals. Families and friends will find a sanctuary here, the villa is modern yet welcoming, offers privacy, and provides easy access to the island’s most vibrant beaches.
Perched atop a hill in Pointe Milou, Villa Upside blends modern island elegance with dramatic panoramic views, for those who appreciate stylish design and serenity.
Architecture & Layout
Spread over two levels, Villa Upside features a luminous great room with floor-to-ceiling glass, flowing seamlessly to a teak terrace and an unforgettable pool hovering above the Caribbean.
Suites & Interiors
Three King Suites:
One on the main level with terrace access and ocean views
Two downstairs, both with en-suite bathrooms and breathtaking vistas
Each is refined with A/C, ceiling fans, HD-TV + Apple TV, iPod docks, safes, and luxurious finishes.
Interior Style: A clean palette of white walls, neutral furnishings, pops of soft color, and sleek lighting, calm, stylish, and modern.
Shared Social Spaces
An open-plan living area with generous couches and a dining table for eight sits next to a fully equipped kitchen with a breakfast bar, framed by ocean views.
Pool & Outdoor Features
The highlight: a visually arresting pool, alongside sunbeds, a teak terrace, and an outdoor dining area with BBQ, perfect for sunsets and lounging.
Signature Service
Every stay at Villa Upside is enhanced by our Signature Service, offering chef and butler services included at no extra cost, crafted to elevate the villa’s contemporary elegance and immersive setting.
- 3 king suites
- Main-level suite with en-suite bathroom, terrace access, and ocean views
- Two lower-level suites with en-suite bathrooms and sea vistas
- En-suite bathrooms with shower, vanity, WC
- Air conditioning and ceiling fans in bedrooms
- HD-TV with Apple TV, iPod docks, safes in each suite
- Fully modern kitchen with dishwasher, espresso & filter coffee makers, oven, breakfast bar
- Open-plan great room with lounge seating and dining table for eight
- Floor-to-ceiling glass with expansive ocean views
- Swimming pool
- Teak terrace with sun loungers
- Outdoor dining area with gas BBQ
- Daily housekeeping (excluding Sundays & holidays)
- Welcome basket
- Airport or pier meet-and-greet
- Pool and garden maintenance
- Linens and beach towels
- Wi-Fi
- Personalized concierge services
- Optional services: private chef, provisioning, spa treatments, yacht charters, babysitting, VIP transfers, event planning
Private Chef & Multilingual Local Butler included, at No Extra Charge
Chef Experience:
- Each villa comes with its own private chef at no extra cost.
- Your private chef will prepare the delicious gourmet dishes that elevate your dining experience during your stay in St Barts.
- Each fine dining experience is customised to your dietary preferences and desires. Sample an vast array of dishes only limited by your desire and your appetite.
- Enjoy your meals upon request, ask for any style of international cuisine your taste buds crave, favourite dishes from back home or explore the local French-Creole cuisine.
- Our chefs specialise in a wide variety of fine dining experiences.
Butler Service:
- Relax with a seamless luxury experience made special by your multilingual butler without the price point of your rental changing.
- We want your stay to be exclusive, private, and tailored to your needs so your only job on the island will be to relax and have fun.
- Discover the island without a language barrier when you stay with us you get a complimentary Multilingual Butler to serve your every need.
- If you don’t speak English, or French, which are the main languages of the island, with your butler you’ll still be able to navigate St. Barts and easily communicate with locals and other travellers.
- Your butler wants to make your experience in St Barts bespoke by: mixing your cocktails, driving to the beach ahead of you to set up umbrellas and lounge chairs, and guide you to popular or exclusive island experiences.
Our Guest Experience Concierge service transforms your St. Barts getaway into an unforgettable luxury experience tailored precisely to your needs.
From the moment you book your villa, our dedicated team works behind the scenes to ensure every aspect of your stay exceeds expectations.
Your personal concierge will:
- Arrange all your transportation from arrival to departure
- Create custom itineraries based on your interests
- Secure reservations exclusive restaurants found in St. Barts
- Organize activities from yacht charters to snorkeling expeditions
- Provide 24/7 travel expertise and guest support services throughout your stay
Our concierge experts hold the secrets that are set to open you to the St. Barts hidden venues and most coveted experiences. For you, they’ll arrange anything you want from a private sunset champagne picnic on a secluded beach to a helicopter tour of St. Barts stunning coastline. Our guest services specialize in making your experience one of a kind.
Leave the details to us while you immerse yourself in the unparalleled beauty and sophistication that makes St. Barts the Caribbean’s crown jewel of luxury travel.
- “Breathtaking panoramic views, magical sunsets and impeccable service. We’re already planning our return!”
- Villa Upside marries contemporary design with tropical comfort, crafting a serene escape that thrills with every sunset.
Perfect For
Families or friends looking for refined design, privacy, and unspoiled views, an effortlessly chic sanctuary set for intimate group stays.
Villa Upside in Pointe Milou, St Barts.
A three-bedroom villa with a dramatic pool, panoramic ocean views, and concierge service. Perfect for families or groups seeking privacy and style.
Villa Upside – Modern Hillside Villa in Pointe Milou, St Barts
See
Gaze out over a glassy pool that seems to disappear into the ocean, with daily views of Lorient Bay and distant islets like Frégate.
Private Chef & Multilingual Local
Butler Included, at No Extra Charge
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Upside
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Outdoor Features
A pool anchors the teak terrace, where sun loungers and shaded spaces invite relaxation. Al-fresco dining with a gas BBQ complements the setting, all framed by sweeping ocean panoramas.
Dining & Living Areas
The air-conditioned great room features comfortable lounge seating and a dining area for eight, enhanced by expansive ocean-facing glazing that fills the space with natural light and breathtaking views.
Kitchen
The fully modern kitchen is equipped with a dishwasher, oven, and both espresso and filter coffee makers. A breakfast bar opens directly into the living areas, creating a functional and social hub for cooking and casual dining.