Windward Vacations

Book a Hotel + Flight together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Windward Hotel Deals

Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9 St. Barthelemy
The price is SARĀ 2,600 per night from Aug 3 to Aug 4
SARĀ 2,600
SARĀ 3,422 total
3 Aug - 4 Aug
includes taxes & fees
9.6/10 Exceptional! (251 reviews)
"Best service in St Barths Loved the pool and view"

Reviewed on 12 July 2026

Christopher Hotel
Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac St. Barthelemy
The price is SARĀ 8,717 per night from Aug 2 to Aug 3
SARĀ 8,717
SARĀ 9,152 total
2 Aug - 3 Aug
includes taxes & fees
9.8/10 Exceptional! (71 reviews)
"We’ve stayed at many luxury resorts around the world, and Rosewood Le Guanahani easily ranks among our favorites. It exceeded every expectation and created memories we’ll cherish for years to come. We cannot wait to return to this extraordinary slice of paradise. Highly recommended."

Reviewed on 6 July 2026

Rosewood Le Guanahani St Barth
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean St. Barthelemy
The price is SARĀ 3,485 per night from Aug 14 to Aug 15
SARĀ 3,485
SARĀ 3,660 total
14 Aug - 15 Aug
includes taxes & fees
9.8/10 Exceptional! (127 reviews)
"We absolutely loved the Tropical. The entire staff, was so friendly and accommodating and the location is absolutely perfect, just a short walk down the hill to our favorite beach! We also loved the food, cocktails and the pool was the perfect spot to relax after a long day. The hotel decor is very ..."

Reviewed on 14 July 2026

Tropical Hotel St Barth
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.