
Leeward Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Leeward Vacation Deals
Price found within the past 48 hours. Click for updated prices.


Le Toiny Hôtel & Beach Club
Toiny
Price was CA $8,800, price is now CA $7,880 per person
CA $7,880
per person
Aug 13 - Aug 20
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Gustavia (SBH)
9.8/10 Exceptional! (51 reviews)
Property is beautiful. The staff is very courteous. The concierge was excellent with restaurant and site seeing suggestions.
Truly enjoyed our stay.
Reviewed on Jun 8, 2026

GYP SEA Saint Barth
Colombier
Price was CA $17,909, price is now CA $17,438 per person
CA $17,438
per person
Aug 13 - Aug 20
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Gustavia (SBH)
9.8/10 Exceptional! (98 reviews)
Very quiet, nice property that allows relaxing and enjoyment of views of the island. Staff very helpful.. we got lost one night and the front desk staff stayed on the phone to guide us back. Any issue was attended to immediately.
Reviewed on Jun 29, 2026


Le Barthélemy Hotel & Spa
Grand Cul-de-Sac
Price was CA $7,907, price is now CA $7,907 per person
CA $7,907
per person
Aug 13 - Aug 17
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Gustavia (SBH)
9.8/10 Exceptional! (90 reviews)
My wife and I travel extensively, and we both agreed: Le Barthélemy has the absolute best service of any hotel we have ever visited. It is a true 6-star experience. The staff genuinely cares and goes out of their way for everything—whether it’s arranging a midnight taxi across the island or preparing a custom breakfast box for an early departure.
Rooms & Amenities
The rooms are spectacular—spacious, modern, and loaded with premium amenities (ours featured a private pool). The property boasts an exceptional spa and a smallish but well-equipped gym that was thankfully empty most of the time. Breakfast was one of the finest we’ve ever had at a luxury resort. Dinner and the restaurant cocktails were superb, though the pool bar drinks weren't quite at that same elite level.
Important Caveats
While this is a flawless stay for us, note a few things depending on what you seek in St. Barth:
The Beach: Incredible for spotting sea turtles and rays, but there is noticeable seaweed, so the water isn't as crystal-clear as other spots.
The Vibe: This is a classy, relaxed sanctuary meant for disconnecting. It is not a party hotel.
Location: Away from the main action in Gustavia, you will need a car or a taxi for nightlife. The hotel makes renting a vehicle effortless, which suited us perfectly as we ventured out daily.
Verdict
An absolute masterpiece of hospitality. If you want unmatched service, spacious luxury, and a serene atmosphere to unwind, look no further.
Reviewed on Jun 20, 2026
Leeward Hotel Deals

GYP SEA Saint Barth
Le Colombier St. Barthelemy
The price is CA $1,021 per night from Jul 9 to Jul 10
CA $1,021
CA $1,073 total
Jul 9 - Jul 10
includes taxes & fees
9.8/10 Exceptional! (100 reviews)
"Very quiet, nice property that allows relaxing and enjoyment of views of the island. Staff very helpful.. we got lost one night and the front desk staff stayed on the phone to guide us back. Any issue was attended to immediately."
Reviewed on Jun 29, 2026

Fouquet's Saint-Barth
Rue des Normands, Lieu Dit Lurin St. Barthelemy Leeward
The price is CA $2,184 per night from Jul 16 to Jul 17
CA $2,184
CA $2,293 total
Jul 16 - Jul 17
includes taxes & fees
9.8/10 Exceptional! (35 reviews)
"Great location, luxury and very comfortable room with great terrace and best view in St Barts. Will be back!"
Reviewed on May 25, 2026

Pearl Beach Hotel
Plage De St. Jean BP1058 St. Barthelemy French West Indies
The price is CA $874 per night from Jul 9 to Jul 10
CA $874
CA $917 total
Jul 9 - Jul 10
includes taxes & fees
9.4/10 Exceptional! (201 reviews)
"Pearl Beach Hotel is one of a kind. We went for my girlfriends birthday and loved every minute of our stay. The staff was amazing throughout our time there - they were attentive, patient and helpful. The manager and front desk staff were awesome and always pleasant. The room was immaculate and spacious. ..."
Reviewed on Jun 8, 2026
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.
Frequently asked questions
What to do in Leeward

Underwater Sculpture Park Snorkel Adventure
CA $62
per adult

High-Speed Ferry to St. Barths
CA $103
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.








