Deals on vacations and trips to Leeward

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Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Price was $4,839, price is now $3,526 per person
$3,526
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Chicago (CHI) 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.
Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
Price was $6,196, price is now $4,584 per person
$4,584
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Gustavia (SBH)
A full-service spa, 2 restaurants, and 2 outdoor pools are all featured at this luxury hotel. Enjoy a day at the beach surfing, or relax with sun loungers. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like full breakfast and valet parking.
Fouquet's Saint-Barth

Fouquet's Saint-Barth

5 out of 5
Lurin
Price was $7,862, price is now $5,864 per person
$5,864
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Gustavia (SBH)
A full-service spa, 2 restaurants, and a 24-hour gym 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.
Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes
Price was $5,243, price is now $3,997 per person
$3,997
per person
Jun 21 - Jun 27
found 1 day ago
Roundtrip flight included
Nashville (BNA) 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.
GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Price was $4,232, price is now $3,578 per person
$3,578
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Gustavia (SBH)
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.

Top Leeward hotels deals

GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Le Colombier St. Barthelemy
$906 nightly
The price is $951 total per night
$951 total
May 3 - May 4
Total with taxes and fees
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.
Pool
Breakfast included
Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes St. Barthelemy
$1,439 nightly
The price is $1,511 total per night
$1,511 total
Apr 29 - Apr 30
Total with taxes and fees
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.
Pool
Breakfast included
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.
Fouquet's Saint-Barth

Fouquet's Saint-Barth

5 out of 5
Rue des Normands, Lieu Dit Lurin St. Barthelemy Leeward
$1,565 nightly
The price is $1,643 total per night
$1,643 total
May 3 - May 4
Total with taxes and fees
A full-service spa, 2 restaurants, and a 24-hour gym 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.
Breakfast included
Spa
Pearl Beach Hotel

Pearl Beach Hotel

Plage De St. Jean BP1058 St. Barthelemy French West Indies
$942 nightly
The price is $989 total per night
$989 total
Apr 5 - Apr 6
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.
Pool
Pet friendly
🏝REAL VILLA ON THE BEACH !SURFSPOT🏝CLOSE TO FLAMANS-STJEAN BEACH .REST.BARS

🏝REAL VILLA ON THE BEACH !SURFSPOT🏝CLOSE TO FLAMANS-STJEAN BEACH .REST.BARS

St. Barthélemy
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This villa features an outdoor pool and a gym. Families will appreciate the playground and barbecue grills. A garden and laundry facilities are also provided.
Pool
Kitchen
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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.

Popular places to visit

Flamands Beach

Flamands Beach

Why not spend a carefree afternoon at Flamands Beach during your travels in Gustavia? Discover the area's museums and shops.

Flamands Beach
Colombier Beach

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.

Colombier Beach

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.

Le P’tit Collectionneur

Photos of local treasures

Browse Leeward vacation photos for more inspiration

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Frequently asked questions

How much are vacation packages to Leeward?
Get ready to be surprised — you can find yourself in Leeward for only $3,526. 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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