Leeward Vacations & Trips from $3,998
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The Latest Leeward Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Tropical Hotel St Barth
Save 100% on your flight
Price was $6,069, price is now $3,998 per person
$3,998
per person
Feb 3 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Gustavia (SBH)
19.6/10 Exceptional! (94 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
Save 100% on your flight
Price was $50,402, price is now $33,937 per person
$33,937
per person
Dec 25 - Jan 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Gustavia (SBH)
19.6/10 Exceptional! (44 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
GYP SEA Saint Barth
Save 100% on your flight
Price was $6,804, price is now $5,276 per person
$5,276
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Gustavia (SBH)
19.6/10 Exceptional! (83 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
Hotel Manapany
Anse des Cayes
Save 100% on your flight
Price was $5,622, price is now $4,491 per person
$4,491
per person
Jan 12 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Gustavia (SBH)
18.8/10 Exceptional! (66 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
Find the Best Leeward Vacation Packages
Leeward Essential Information
Language | French |
|---|---|
Currency | Euros |
Local Welcome | Salut / Bonjour |
Local Goodbye | Au revoir / À bientôt |
Closest Airport | Gustaf III Airport (SBH) |
Leeward Hotel Deals
GYP SEA Saint Barth
Le Colombier St. Barthelemy
$980 nightly
The price is $1,029 total per night from Nov 19 to Nov 20
$1,029 total
Nov 19 - Nov 20
Total with taxes and fees
9.6/10 Exceptional! (83 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 ...
Reviewed on Aug 1, 2025
Hotel Barrière Le Carl Gustaf St Barth
Rue des Normands, Lieu Dit Lurin St. Barthelemy Leeward
$2,028 nightly
The price is $2,129 total per night from Nov 23 to Nov 24
$2,129 total
Nov 23 - Nov 24
Total with taxes and fees
9.6/10 Exceptional! (26 reviews)
A superb hotel in Gustavia with easy access to beach and dining
Reviewed on Aug 2, 2025
Pearl Beach Hotel
Plage De St. Jean BP1058 St. Barthelemy French West Indies
$563 nightly
The price is $591 total per night from Nov 20 to Nov 21
$591 total
Nov 20 - Nov 21
Total with taxes and fees
9.2/10 Wonderful! (185 reviews)
The staff here was amazing. When we went to the airport, my girlfriend actually left a dress in our room. The staff grab the dress drove to the airport and gave us the address while we were waiting for our flight about to board! The restaurant here was incredible. The lobster was absolutely amazing. ...
Reviewed on Oct 7, 2025
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.
Discover the most popular places to visit in Leeward
Flamands Beach
Why not spend a carefree afternoon at Flamands Beach during your travels in Gustavia? Discover the area's museums and shops.
Colombier Beach
If a restful vacation is part of your travel plans, Colombier Beach might be the perfect place to seek out during your trip to Colombier.
Le P’tit Collectionneur
You can spend an afternoon studying the exhibits at Le P’tit Collectionneur during your travels in Gustavia. Stroll along the beaches or visit the spas in this romantic area.
What to do in Leeward
St-Martin and St Maarten: Sightseeing Tour of the French and Dutch Sides of the Island
$56
per adult
80% of travellers recommend
5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix
$139
per adult
100% of travellers recommend
St Maarten Shore Excursion: Maho Beach Round-Trip Transfer
$28
per adult
100% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.