Villa Upside on St. Barts provides the ultimate in indoor/outdoor living in Pointe Milou on the magical island of St. Barts. This chic, brand new villa is designed with special architectural touches that put you in touch with the natural beauty all around. An infinity edge pool seems to blend with the azure blue ocean, and strategic placement of see-through panels insures panoramic views of Freggate Island and the surrounding waters from the pool terrace.
Villa Upside is decorated with contemporary yet comfortable furnishings in a neutral color scheme punctuated by splashes of blue and green to echo the colors of the island. The layout features an open design with the living area, gourmet kitchen and pool terrace flowing together to create an exceptional setting for lounging, entertaining and relaxing.
Guests will enjoy spectacular ocean views from each of the three ensuite bedrooms. For added luxury and convenience, the bedrooms are air-conditioned and provide flat screen TV, DVD players and a security safe. The kitchen is separated from the dining area by a breakfast bar and includes amenities like a dishwasher, a microwave and an espresso machine. There is an outdoor gas barbecue to prepare quick and easy meals to be served at the dining room table or al fresco overlooking island greenery and the ocean. Stay connected with WiFi Internet access throughout.
Villa Upside is situated in popular Point Milou near the beautiful beach of Lorient, the Christopher Hotel and just a short walk from the fabulous restaurants that make St. Barts so famous. Ask about the attractive pricing available for this gorgeous St. Barts villa.
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
- WiFi
- Housekeeper(s)
- Pool Person
- The pools are heated only from November 15th to April 30th period. Outside of these dates, pool heating is available on request for an additional cost.
- Welcome basket
- Outdoor
- Private
| SEASON | BEDROOMS | DAILY | WEEKLY | |||||||||
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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 21 November 15, 2026 - November 21, 2026 (7 night minimum) |
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| 2026 Nov 21 to Nov 28 November 21, 2026 - November 28, 2026 (7 night minimum) |
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| 2026 Nov 28 to Dec 15 November 28, 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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| 2027 Apr 15 to Apr 20 April 15, 2027 - April 20, 2027 (5 night minimum) |
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| 2027 Apr 20 to Aug 31 April 20, 2027 - August 31, 2027 (5 night minimum) |
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| 2027 Aug 31 to Nov 15 August 31, 2027 - November 15, 2027 (5 night minimum) |
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| 2027 Nov 15 to Nov 23 November 15, 2027 - November 23, 2027 (7 night minimum) |
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| 2027 Nov 23 to Nov 30 November 23, 2027 - November 30, 2027 (7 night minimum) |
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| 2027 Nov 30 to Dec 15 November 30, 2027 - December 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
- 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.
- 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 *
- Excursions
- Experiences & Activities
- In Villa Spa Services *
- Private Charters *
- Provisioning/Pre-Stocking
- Rental Cars with Free Delivery *
- Rental Equipment (crib, kayak, etc)
- VIP Fast Track Arrivals *
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.
Plan an unforgettable vacation by booking some of our favorite experiences that our
guests loved.
Recommended St Barts Experiences
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 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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Winter Sale Event – Receive Up to US$ 1,000 in Concierge Credit
Book your winter villa escape and enjoy up to US$ 1,000 in concierge credit to elevate your stay with private chefs, spa services, yacht charters, rental cars, airport transfers, and curated experiences.
Offer ends: February 4, 2026
Winter Concierge Credit Tiers
• US$ 200 concierge credit on bookings between US$ 5,000 and US$ 9,999
• US$ 500 concierge credit on bookings between US$ 10,000 and US$ 19,999
• US$ 1,000 concierge credit on bookings of US$ 20,000 or more
Booking window: January 20– February 4, 2026
Terms and conditions
• Credit is based on total booking value before taxes and fees
• Credit applies to experiences only and cannot be used toward villa rental, taxes, or fees
• Credit must be used during the booked stay and expires at checkout
• Cannot be combined with other offers and has no cash value
• Valid only on new reservations made within the booking window
Offer cannot be combined with other offers | Offer based on availability | Minimum night stay required | Non-transferrable | No cash value | Promotion is only valid on new reservations | Black-out dates may apply | Rates subject to tax and service charge | Credit can only be used on one selected service and cannot be split between multiple services.
Availability subject to change.
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