Leeward Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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Top Leeward Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
per person
Oct 16 - Oct 19
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to Gustavia (SBH)
10/10 Exceptional! (38 reviews)
Super on the accommodations! Enjoyed the privacy and offered many extras! But, time to change the mattress, window blinds do not work and the grounds need a some attention. Other than that it was definitely a pleasant experience

Reviewed on Jun. 2, 2025

Leeward Hotel Deals

GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Le Colombier, St. Barthelemy
The price is CA $1,008 per night from Aug 16 to Aug 17
CA $1,008
CA $1,058 total
Aug 16 - Aug 17
includes taxes & fees
9.6/10 Exceptional! (78 reviews)
"Definitely recommend"

Reviewed on Jul. 9, 2025

GYP SEA Saint Barth
Pearl Beach Hotel

Pearl Beach Hotel

Plage De St. Jean BP1058, St. Barthelemy, French West Indies
The price is CA $779 per night from Jul 26 to Jul 27
CA $779
CA $818 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (175 reviews)
"Fantastic place Strongly recommend !"

Reviewed on Jul. 16, 2025

Pearl Beach Hotel
Reve de Saint Barth

Reve de Saint Barth

Les Hauts de Flamands, Merlette, St. Barthelemy
The price is CA $659 per night from Aug 4 to Aug 5
CA $659
CA $695 total
Aug 4 - Aug 5
includes taxes & fees
9.8/10 Exceptional! (41 reviews)
"Excellent! Definitely recommend!"

Reviewed on Feb. 19, 2025

Reve de Saint Barth
See all 1,458 properties in Leeward
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Leeward vacation package cost?
The most affordable Leeward vacation package is CA $4,236, so the trip of your dreams can become a reality — without burning a hole in your pocket. Combine flights, hotels and car rentals to customize a package that matches your traveling style.
How do I get a cheap travel package to Leeward?
Crafting your own Leeward vacation package with Expedia is one of the best ways to save. We offer access to over 550 air carriers and 1,000,000 properties across the globe. With such an amazing range to select from, you'll have no trouble pulling together your perfect getaway.
How far in advance should I book my Leeward vacation?
Get rewarded with the widest variety and the cheapest prices by booking your Leeward adventure early. Air carriers generally release flight tickets around a year before departure, so reserve your spot as soon as you can. That said, Expedia is committed to giving you the best deals around, so it's always a good time to book your dream vacation!
What does an Expedia Leeward travel package include?
Hotels, flights and a shiny set of wheels for all your fun road trip adventures. Simply choose your favorite bundle and gain access to great discounts. Once you've made your booking, add on a couple of experiences and tours and watch your savings grow. When it comes to creating your Leeward escape, you're the one in control!
What should I know before booking a Leeward travel package?
A package can be easier on the bank balance than separately booking all you need for your trip. For example, combine your flights, hotels and rental cars and save a packet. No matter your vacation plans, there's bound to be a package that best suits your budget.
Can I choose my airline with a Leeward Expedia vacation package?
Yes, you're in control. We offer more than 550 partner airlines globally, so you can customize your Leeward vacation according to your needs and budget.
If I'm not able to travel, can I cancel my Leeward vacation package?
Don't worry if you're rethinking your Leeward vacation package — you can cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We get that your circumstances can suddenly change, so look up our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.

What to do in Leeward

High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

CA $102
per adult
76% of travellers recommend
High-Speed Ferry to St. Barths
Panoramic view of vibrant St. Martin

Edge Ferry Tickets to St. Barts

CA $137
per adult
84% of travellers recommend
Edge Ferry Tickets to St. Barts
Lunch at Meads BAy

Ultimate Prickly Pear and Anguilla Experience

CA $203
per adult
82% of travellers recommend
Ultimate Prickly Pear and Anguilla Experience
See all activities in Leeward
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.