The scenery of Pointe Milou, on St. Barts, is known for being inspiring and stunning. However, the design of the Villa Upside on St Barts somehow manages to enhance the already fabulous views. The three-bedroom villa is set atop a hill and features an impressive terrace and infinity pool that put guests directly into the amazing views and settings.
Fregate Island will greet visitors each day, and whether they are enjoying it while taking a swim in the elegant pool or from the many lounge, dining, and vantage points, it will never cease to inspire. The open floor plan and the enormous walls of glass that accent all areas of this villa also guarantee that a sense of the outdoors is always present.
The large indoor living area is adjacent to the luxurious gourmet kitchen that features everything from an espresso machine to a dishwasher. Al fresco dining is possible, thanks to the open floor plan, and a separate terrace with gas barbecue supplies guests with the truly ultimate in relaxed and casual dining. The breakfast bar is great for completely relaxed morning coffee or even for a casual cocktail in the evenings.
The Villa Upside is split between two levels. Two of the large and luxurious bedrooms are on a lower level and enjoy large en suite bathrooms, and wonderful ocean views. A third bedroom is on the main floor and also features a lovely sea view and is designed with a king sized bed. The entire villa has Wi-Fi, and the living room features a full array of electronics suited for entertainment.
Though the villa is close to several popular shopping and dining areas, and just moments from Lorient Beach, you may find it hard to tear yourself away from this location. Offering a family or a small group the most private and yet full-featured accommodation, it is the perfect place to experience St. Barts.
We booked through St. Barths Blue and couldn't be more pleased with their service from start to finish. Rhona at St. Barths Blue deserves particular recognition for truly understanding our needs and accomplishing every request we made. Her attentiveness to our preferences and responsive communication made planning our stay completely stress-free. She anticipated details we hadn't even considered, ensuring our villa experience was perfectly tailored to our tastes.
Our stay at Villa Upside on Pointe Milou was nothing short of magical. Perched on the hillside with breathtaking panoramic views of the Caribbean, this villa exceeded all our expectations.
Our experience began wonderfully when Lucien, the concierge, personally greeted us at the ferry and efficiently organized our luggage transfer. Throughout our stay, his attentiveness was remarkable - arranging dinner reservations at short notice, organizing a sunset sailing trip, and even surprising us with fresh local pastries one morning. No request was too small or too complicated; Lucien handled everything with grace and efficiency.
The cleanliness of Villa Upside deserves special mention. The housekeeping team performed extraordinary daily service, leaving the villa immaculate. From perfectly pressed linens to spotless floors and gleaming surfaces, their attention to detail was exceptional. Even the outdoor areas were meticulously maintained, with pool areas refreshed each morning before we awoke.
Between the stunning location on Pointe Milou, the luxurious amenities, Lucien's exceptional concierge service, and the impeccable cleanliness, Villa Upside provided the perfect sanctuary for our St. Barths getaway. We're already planning our return!
We booked through St. Barths Blue and couldn't be more pleased with their service from start to finish. They found us the perfect villa to match our needs and ensured everything was arranged flawlessly.
The Villa was in great shape and had everything we needed. We had excellent service from the concierges as well.
This villa was amazing. From the decor to the views!! We loved it. Only thing would be to heat the pool. It was chilly at times and we didn’t use it as much because of this.
Great service and very nice.
Very comfortable. Everything I needed.
We found this villa to be beyond our expectations. The view was stellar and the sunsets were spectacular! We were happy that there was umbrellas, beach chairs, and snorkel equipment available for our use. The villa is located in a fairly built up area, but we still felt it was private enough to "skinny dip" in the very nice infinity pool. The kitchen was very well equipped and easy to use.
Everything about our stay was perfect! The villa is gorgeous and the layout is ideal--we didn't need the downstairs so the master and upper floor is perfect for a couple. The view is the best on the island. So peaceful but not isolated. We WILL be back!! Our greeter Clement gave us some great tios and refreshed our memory of the island so we knew exactly where we wanted to go and how to find anything we needed.
Very comfortable. Has everything you might need. Amazing views!
Bedroom 1: Main floor bedroom with a king-size bed, ceiling fan, A/C, TV, WiFi, safe, sea view, access to the pool, and en-suite bathroom with shower, vanity and WC. 2 guests maximum.
Bedroom 2: Lower floor bedroom with a king-size bed, ceiling fan, A/C, TV, WiFi, safe, sea view, and en-suite bathroom with shower, vanity and WC. 2 guests maximum.
Bedroom 3: Lower floor bedroom with a king-size bed, ceiling fan, A/C, TV, WiFi, safe, sea view, and en-suite bathroom with shower, vanity and WC. 2 guests maximum.
Interior Access Bedrooms: 3
- Air Conditioning - Bedrooms
- Apple TV
- Blender
- Ceiling Fans
- Coffee Maker
- Coffee Maker (Espresso/Nespresso)
- Dishwasher
- DVD Player
- Internet
- iPod Dock
- Iron
- Microwave
- Outdoor Grill - Gas
- Safe
- Smart TV
- TV - Flat-Screen
- View - Ocean/Sea
- Voltage - 220
- WiFi
- Housekeeper(s)
- Pool Person
- Outdoor
- Private
| SEASON | BEDROOMS | DAILY | WEEKLY | |||||||||
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| 2025 Apr 15 to Aug 31 April 15, 2025 - August 31, 2025 (5 night minimum) |
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| 2025 Aug 31 to Nov 15 August 31, 2025 - November 15, 2025 (5 night minimum) |
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| 2025 Nov 15 to Nov 23 November 15, 2025 - November 23, 2025 (7 night minimum) |
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| 2025 Nov 23 to Nov 30 November 23, 2025 - November 30, 2025 (7 night minimum) |
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| 2025 Nov 30 to Dec 15 November 30, 2025 - December 15, 2025 (7 night minimum) |
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| 2025 Dec 15 to Dec 19 December 15, 2025 - December 19, 2025 (7 night minimum) |
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| 2025 Dec 19 to Dec 27 December 19, 2025 - December 27, 2025 (14 night minimum) |
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| 2025 Dec 27 to 2026 Jan 11 December 27, 2025 - January 11, 2026 (14 night minimum) |
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| 2026 Jan 11 to Mar 9 January 11, 2026 - March 9, 2026 (7 night minimum) |
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| 2026 Mar 9 to Mar 16 March 9, 2026 - March 16, 2026 (7 night minimum) |
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| 2026 Mar 16 to Apr 15 March 16, 2026 - April 15, 2026 (7 night minimum) |
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| 2026 Apr 15 to Apr 20 April 15, 2026 - April 20, 2026 (5 night minimum) |
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| 2026 Apr 20 to Aug 31 April 20, 2026 - August 31, 2026 (5 night minimum) |
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| 2026 Aug 31 to Nov 15 August 31, 2026 - November 15, 2026 (5 night minimum) |
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| 2026 Nov 15 to Nov 23 November 15, 2026 - November 23, 2026 (7 night minimum) |
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| 2026 Nov 23 to Nov 30 November 23, 2026 - November 30, 2026 (7 night minimum) |
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| 2026 Nov 30 to Dec 15 November 30, 2026 - December 15, 2026 (7 night minimum) |
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| 2026 Dec 15 to Dec 19 December 15, 2026 - December 19, 2026 (7 night minimum) |
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| 2026 Dec 19 to Dec 27 December 19, 2026 - December 27, 2026 (14 night minimum) |
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| 2026 Dec 27 to 2027 Jan 11 December 27, 2026 - January 11, 2027 (14 night minimum) |
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| 2027 Jan 11 to Mar 12 January 11, 2027 - March 12, 2027 (7 night minimum) |
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| 2027 Mar 12 to Mar 19 March 12, 2027 - March 19, 2027 (7 night minimum) |
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| 2027 Mar 19 to Apr 15 March 19, 2027 - April 15, 2027 (7 night minimum) |
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Rates based on 6 guests.
Note: The rates above are subject to 15% Tax/Service Charge.
Payments accepted in US Dollars, Canadian Dollars, Euros, British Pound, Swiss Franc, Australian Dollars, New Zealand Dollars.
Major credit cards accepted in US Dollars.
Rates are subject to change without prior notice.
- Reservation deposit is 30%. Full balance is due 90 days prior to arrival.
- Holiday/Festive Booking Condition: 50% deposit required. Balance due by September 1st.
- Cancellation Policy: All payments are nonrefundable.
- Check In / Check Out: 4pm / 11am
- Damage Deposit: US $1000
- Restricted to age 15 years and above
- Pets allowed with permission
- No Smoking
- Housekeeping: Daily maid service except Sundays & holidays
- Airport meet and greet with escort
- All bookings that include Christmas Day or New Year Day will be charged at the Peak Season Rate and for a minimum of 14 days. Shorter stays are only on request, but for a minimum of 7 days (Christmas week or NYE Week).
- All payments are nonrefundable
- Head guests must be over 21 years of age and be present at check-in and check-out.
- Provisions and groceries are not included
- Rates are set in US Dollars. Prices in other currencies may fluctuate.
- The pools are heated only from November 15th to April 30th period. Temperature is between 27 °- 30 °C
- Villa orientation
Once a vacation home is selected, the pampered adventure begins. Our concierge team will assist with creating a magical and immersive vacation experience. Our services include
- Arrival Logistics & Transfers
- Chef and Catering Services
- Experiences & Activities
- In Villa Spa Services
- Private Charters
- Provisioning/Pre-Stocking
- Rental Cars
- Rental Equipment (crib, kayak, etc)
- Ferry Ticketing
- Tradewind Flight Charters
While available for advanced requests, the concierge team connects with guests 30 days prior to arrival to coordinate arrivals and to reserve desired services and experiences. Guests with scheduled Christmas/New Year stays will be contacted 90 days prior to arrival.
For example, a 5 bedroom villa that offers a 3 bedroom rate will be the exclusive use of the guest but two bedrooms and their en-suite bathrooms will be locked off. Capacity is capped at 2 guests per bedroom.
Once a reservation is confirmed, a concierge will welcome you to the planning stages of your vacation to assist with arrival logistics, rental cars, transfers, and a host of concierge services.
The arrival procedures due vary from villa to villa, select villas may include welcome provisioning while other properties will provide basic arrival information.
For more details, please visit Travel Protection
In the near future, we expect to accept a greater variety of payment methods and currencies via Stripe.
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Complimentary Rental Car
Book a 5-night stay or longer with a minimum weekly rate of US$ 7000 or more, and enjoy a Kia Picanto complimentary rental car.
Terms and Conditions:
- Promotion valid for new bookings made between May 28 and July 31, 2025.
- Not valid for Festive dates.
- Credit is non-transferable and has no cash value.
- Upgrade to other vehicles for an additional charge.
- Services are subject to availability and must be booked in advance.
- Other terms and conditions may apply.
Indulge in a luxurious escape with our St. Barts Promotion and make your stay unforgettable!
Blackout Dates: November 22, 2025 - November 29, 2025
December 15, 2025 - January 11, 2026
November 21, 2026 - November 28, 2026
December 15, 2026 - January 11, 2027
Offer ends: July 31, 2025 Guest is responsible for gas, taxes and insurance | Offer includes only the base rate of rental car | Upgrades available for an additional charge | Offer cannot be combined with other offers | Offer based on availability | Minimum night stay required | Non-transferrable | No cash value | Guest is responsible for price difference on upgraded models | Guest is liable for damages, theft or injury resulting from use of rental car | Rental car must be reserved and coordinated by the concierge | Guest is responsible for ensuring adequate insurance coverage
Availability subject to change.
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