
Leeward Vacations & Trips from $1,838
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The Latest Leeward Vacation Packages
Price found within the past 48 hours. Click for updated prices.

GYP SEA Saint Barth
Colombier
Price was $2,232, price is now $1,838 per person
$1,838
per person
Aug 7 - Aug 11
found 21 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 Toiny Hôtel & Beach Club
Toiny
Price was $3,082, price is now $2,492 per person
$2,492
per person
Aug 7 - Aug 11
found 21 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) 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

Hotel Manapany
Anse des Cayes
Price was $2,716, price is now $2,268 per person
$2,268
per person
Aug 3 - Aug 6
found 18 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Gustavia (SBH)
9.4/10 Exceptional! (71 reviews)
Lovely, “barefoot chic” hotel that is top class in all respects
Reviewed on Apr 27, 2026

Fouquet's Saint-Barth
Lurin
Price was $3,893, price is now $3,383 per person
$3,383
per person
Aug 7 - Aug 11
found 21 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Gustavia (SBH)
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
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
$682 nightly
The price is $717 total per night from Jul 22 to Jul 23
$717 total
Jul 22 - Jul 23
Total with taxes and 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
$1,383 nightly
The price is $1,452 total per night from Aug 1 to Aug 2
$1,452 total
Aug 1 - Aug 2
Total with taxes and 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
$614 nightly
The price is $645 total per night from Jul 4 to Jul 5
$645 total
Jul 4 - Jul 5
Total with taxes and 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.
What to do in Leeward

Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
$159
per adult
90% of travellers recommend

For hotel guests: Guided ATV Tour Dutch/French St. Maarten - Highlights & Beach
$120
per traveler
100% of travellers recommend
Explore a world of travel with Expedia
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