Deals on vacations and trips to Leeward

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Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes
Save 100% on your flight
Price was $4,311, price is now $3,281 per person
$3,281
per person
Nov 5 - Nov 9
found 20 hours ago
Roundtrip flight included
Baltimore (BWI) to Gustavia (SBH)
A full-service spa, 2 outdoor pools, and a gym are all featured at this luxury hotel. Enjoy a day at the beach snorkeling, or relax with sun loungers. Bring the family and enjoy the children's pool, playground, and arcade/game room.
Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
Toiny
Save 100% on your flight
Price was $5,784, price is now $3,755 per person
$3,755
per person
Nov 5 - Nov 9
found 20 hours ago
Roundtrip flight included
Baltimore (BWI) to Gustavia (SBH)
This luxury hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas and airport shuttle. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like full breakfast and valet parking.
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Saint-Jean
Save 100% on your flight
Price was $5,211, price is now $3,927 per person
$3,927
per person
Nov 11 - Nov 15
found 17 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Gustavia (SBH)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and free airport shuttle. Relax with a drink at the poolside bar and enjoy free perks like full breakfast and valet parking.
Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou
Save 100% on your flight
Price was $4,970, price is now $4,197 per person
$4,197
per person
Nov 5 - Nov 9
found 20 hours ago
Roundtrip flight included
Baltimore (BWI) to Gustavia (SBH)
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this luxury hotel. Families will appreciate the children's pool, onsite laundry facilities, and in-room childcare. Enjoy the gym and free perks like buffet breakfast and valet parking.
Fouquet's Saint-Barth

Fouquet's Saint-Barth

5 out of 5
Lurin
Price was $6,136, price is now $5,492 per person
$5,492
per person
Nov 5 - Nov 9
found 20 hours ago
Roundtrip flight included
Baltimore (BWI) to Gustavia (SBH)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and free airport shuttle. Relax with a drink at the bar/lounge and enjoy free perks like cooked-to-order breakfast and valet parking.

Top Leeward hotels deals

GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Le Colombier St. Barthelemy
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A full-service spa, an outdoor pool, and a restaurant are all featured at this luxury hotel. Enjoy the gym and free perks like continental breakfast and valet parking. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.
Fouquet's Saint-Barth

Fouquet's Saint-Barth

5 out of 5
Rue des Normands, Lieu Dit Lurin St. Barthelemy Leeward
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A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and free airport shuttle. Relax with a drink at the bar/lounge and enjoy free perks like cooked-to-order breakfast and valet parking.
Pearl Beach Hotel

Pearl Beach Hotel

Plage De St. Jean BP1058 St. Barthelemy French West Indies
$625 nightly
The price is $656 total per night
$656 total
Aug 21 - Aug 22
Total with taxes and fees
This hotel features 2 bars/lounges, a beach bar, and a restaurant. Dine at the beachfront restaurant and relax with beach umbrellas. Enjoy the outdoor pool and perks like free self parking and a free ferry terminal shuttle.
Reve de Saint Barth

Reve de Saint Barth

Les Hauts de Flamands, Merlette St. Barthelemy
Get rates
The hotel doesn't skimp on freebies - guests receive free on-the-go breakfast and free self parking. Business travelers can take advantage of the laundry service. Enjoy the indoor pool and conveniences like a terrace and concierge services.
Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes St. Barthelemy
Get rates
A full-service spa, 2 outdoor pools, and a gym are all featured at this luxury hotel. Enjoy a day at the beach snorkeling, or relax with sun loungers. Bring the family and enjoy the children's pool, playground, and arcade/game room.
Beautiful 2-bedroom apartment in Gustavia with harbor view in Saint Barthélémy

Beautiful 2-bedroom apartment in Gustavia with harbor view in Saint Barthélémy

Gustavia Saint Barthélémy
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Stay at this apartment in St. Barthelemy. Enjoy balconies, an in-room coffeemaker, and housekeeping. Popular attractions Gustavia Harbor and Fort Karl are located nearby.
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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.

Photos of local treasures

Browse Leeward vacation photos for more inspiration

A coastal town with colorful buildings, a marina with boats, and a mountainous backdrop.
A coastal town with a marina filled with boats, surrounded by lush green hills and red-roofed buildings.
A coastal town with red-roofed houses, a marina with boats, and a clear blue sky.
A building with a sign reading "Old Alma," a balcony, and a parked car.
A coastal landscape with a view of the ocean, a sailboat, and a cluster of houses with red roofs.

Frequently asked questions

How much are vacation packages to Leeward?
Get ready to be surprised — you can find yourself in Leeward for only $3,281. At Travelocity, we save you money and hassle with our awesome vacation package deals. With experiences, hotels and flights all available at our one-stop shop, what's holding you back?
Where can I get the best vacation package deals for Leeward?
Travelocity has endless ways to score an incredible Leeward package deal. Select from 400 airlines and 1,000,000 properties worldwide and craft a travel itinerary that's right for you. With almost endless choice, you'll have plenty of inspiration for your next big adventure.
Why should I purchase my Leeward vacation package with Travelocity?
With our Price Match Guarantee, we'll match any cheaper price you find. Add to that our 24/7 customer support and top-shelf service and your perfect vacation is well within reach.
Can I save money on my Leeward car rental if I bundle it with a hotel or flight?
Definitely. And our Leeward vacation packages are the best way to do it. In just a few clicks you can save cash as well as time by bundling your bookings. Pick up the keys to your rental car then chart your own course. Looking for things to do? Add a few tours to your package and make savings on those too.
Which airport is best for Leeward?
Princess Juliana Intl. Airport (SXM) is where many travelers choose to touch down. Depending on your Leeward itinerary, Robert L. Bradshaw Intl. Airport (SKB) and Clayton J. Lloyd Intl. Airport (AXA) are also worth considering.

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