Leeward Vacation Packages

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Top Leeward Vacation Deals

Price found within the past 48 hours. Click for updated prices.
GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Price was CA $8,685, price is now CA $6,920 per person
CA $6,920
per person
Nov 24 - Nov 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Gustavia (SBH)
9.8/10 Exceptional! (82 reviews)
We loved this hotel, however there were no locks on the door of one of the bedrooms in our suite. The room could be accessed from the outside. The hotel is on a beautiful hilltop but, we couldn’t let our kids sleep in that room. The hotel had no way to rectify. The hotel and staff are amazing but that would be a consideration for not returning to the 3 bedroom suite.

Reviewed on Aug. 1, 2025

Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Price was CA $13,694, price is now CA $9,931 per person
CA $9,931
per person
Nov 24 - Nov 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Gustavia (SBH)
9.8/10 Exceptional! (91 reviews)
Expensive but it's St Barts as expected...this an amazing hotel.,loved the location, the views, the service,the rooms and Beeakfast was good as well..will definitely go back again.10/10

Reviewed on Jul. 31, 2025

Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
Price was CA $12,861, price is now CA $10,272 per person
CA $10,272
per person
Nov 24 - Nov 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Gustavia (SBH)
9.8/10 Exceptional! (43 reviews)
It was perfect . It’s a beautiful property and the service was a dream. They thought about and catered to everything proactively.

Reviewed on Aug. 4, 2025

Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes
Price was CA $9,075, price is now CA $8,040 per person
CA $8,040
per person
Nov 24 - Nov 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Gustavia (SBH)
9.4/10 Exceptional! (64 reviews)
The property was exquisite. The entire staff was incredible, especially Noémie from Reception. She went above and beyond to make our 11th anniversary very memorable. I am already looking forward to a more extended visit to Hotel Manapany.

Reviewed on Jun. 15, 2025

Hotel Barrière Le Carl Gustaf St Barth

Hotel Barrière Le Carl Gustaf St Barth

5 out of 5
Lurin
Price was CA $14,445, price is now CA $13,211 per person
CA $13,211
per person
Nov 24 - Nov 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Gustavia (SBH)
9.8/10 Exceptional! (26 reviews)
A superb hotel in Gustavia with easy access to beach and dining

Reviewed on Aug. 2, 2025

Leeward Hotel Deals

GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Le Colombier, St. Barthelemy
Get rates
GYP SEA Saint Barth
Reve de Saint Barth

Reve de Saint Barth

Les Hauts de Flamands, Merlette, St. Barthelemy
The price is CA $624 per night from Sep 2 to Sep 3
CA $624
CA $655 total
Sep 2 - Sep 3
includes taxes & fees
Reve de Saint Barth
Pearl Beach Hotel

Pearl Beach Hotel

Plage De St. Jean BP1058, St. Barthelemy, French West Indies
The price is CA $780 per night from Sep 2 to Sep 3
CA $780
CA $819 total
Sep 2 - Sep 3
includes taxes & fees
Pearl Beach Hotel
See all 1,428 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 $6,920, 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 $103
per adult
76% of travellers recommend
High-Speed Ferry to St. Barths
Lunch at Meads BAy

Ultimate Prickly Pear and Anguilla Experience

CA $205
per adult
82% of travellers recommend
Ultimate Prickly Pear and Anguilla Experience
Sightseeing Tour of the French and Dutch Sides of the Island

St-Martin and St Maarten: Sightseeing Tour of the French and Dutch Sides of the Island

CA $77
per adult
80% of travellers recommend
St-Martin and St Maarten: Sightseeing Tour of the French and Dutch Sides of the Island
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.