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Flights to Leeward starting at

Have you been telling yourself, “2025 is the year I travel more and sit less”? Well, here we are and there you are. So, where are you going? Looks like a flight to Leeward is calling. Good thing we can help you bag that flight out of town for cheap, so you can get your resolutions resolved.

Travel like you mean it

When you land it’s not straight to the tourist traps for you. You have things to do and see in Leeward that aren’t on a map or in the “Best of. . .” guides. You know this region is filled with hidden haunts, locals-only know favorites, and the off-beat-so-weird-it’s-amazing places. And you plan to find every last one of them. Good thing you’ll save a grip of cash on your flight so you can daytrip far and wide.

You won’t have to wing it

So how do you score that killer deal on a flight to Leeward? Easy, go through us. These aren’t pie in the sky deals, but ones you can actually score. Filter flights to Leeward by:

  • Hotwire Hot Rate: Do you have a flexible schedule? Hit up the Hotwire Hot Rate and land a super cheap flight to Leeward. We’ll reveal the airline and exact time after you book.
  • Price: How low can we go? Find out. We have prices from to .
  • Duration: Want to get to Leeward as fast as you can? Or maybe you don’t mind taking your time to save a few bucks here and there.
  • Departure or Arrival: Like to arrive in the a.m. to get your day going? Or are you a night owl that knows the best fun happens late night? The choice is yours.

So are you going to live up to those travel plans or kick the can to next year? Book your flight to Leeward today and get going.

Last Minute Hotel Deals in Leeward

GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Le Colombier, St. Barthelemy
The price is $1,078 per night from Apr 11 to Apr 12
$1,078
per night
Apr 11 - Apr 12
Stay at this 5-star luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free valet parking. Popular attractions Gustavia Harbor and Flamands ...
9.6/10 Exceptional! (64 reviews)
"Absolutely the best !!!!!!! I would return in a heartbeat!"

Reviewed on Feb 14, 2025

GYP SEA Saint Barth
Hotel Barrière Le Carl Gustaf St Barth

Hotel Barrière Le Carl Gustaf St Barth

5 out of 5
Rue des Normands, Lieu Dit Lurin, St. Barthelemy, Leeward
The price is $1,799 per night from Apr 13 to Apr 14
$1,799
per night
Apr 13 - Apr 14
Stay at this 5-star luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free valet parking. Popular attractions Gustavia Harbor and Plage du ...
9.6/10 Exceptional! (21 reviews)
"By far one of the best hotels on the island From service to dining beach . Great staff always friendly and ready to accommodate all your needs."

Reviewed on Feb 3, 2025

Hotel Barrière Le Carl Gustaf St Barth
Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes, St. Barthelemy
The price is $1,272 per night from Apr 7 to Apr 8
$1,272
per night
Apr 7 - Apr 8
Stay at this 5-star luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Gustavia Harbor and Anse des Cayes ...
9.4/10 Exceptional! (62 reviews)
"It's a nice place to stay. It's a solid 4 star hotel. Lovely people that work there. I would recommend LE Toiny for an Extraordinary stay - but it is also about 1.5-2x the price The location of this hotel is good. It's close to St Jean (where EdenRoc is, Nikki Beach and Gyp Sea) and close to Gustavia. ..."

Reviewed on Jan 10, 2025

Hotel Manapany
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Pearl Beach Hotel

Pearl Beach Hotel

Plage De St. Jean BP1058, St. Barthelemy, French West Indies
The price is $841 per night from Mar 17 to Mar 18
$841
per night
Mar 17 - Mar 18
Book a stay at this beach hotel in St. Barthelemy. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Gustavia Harbor and St. Jean Beach ...
9.2/10 Wonderful! (159 reviews)
"Beach front near the Eden Rock. Perfect little boutique hotel where you can eat breakfast two feet from the sand. Large, modern rooms. Great stay."

Reviewed on Feb 16, 2025

Pearl Beach Hotel
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.