Deals on vacations and trips to Leeward

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Leeward flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Christopher Hotel

Christopher Hotel

5 out of 5
Save 100% on your flight
Price was $5,483, price is now $3,866 per person
$3,866
per person
Feb 16 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) 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.
Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes
Save 100% on your flight
Price was $6,659, price is now $3,989 per person
$3,989
per person
Feb 16 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) 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.
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Save 100% on your flight
Price was $6,143, price is now $3,879 per person
$3,879
per person
Feb 16 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) 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
Save 100% on your flight
Price was $12,901, price is now $9,256 per person
$9,256
per person
Mar 1 - Mar 7
found 23 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) 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.
GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Save 100% on your flight
Price was $5,104, price is now $3,890 per person
$3,890
per person
Feb 16 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) 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
$1,439 nightly
The price is $1,511 total per night
$1,511 total
Jan 12 - Jan 13, 2026
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
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.
Pool
Breakfast included
Hotel Barrière Le Carl Gustaf St Barth

Hotel Barrière Le Carl Gustaf St Barth

5 out of 5
Rue des Normands, Lieu Dit Lurin St. Barthelemy Leeward
$2,649 nightly
The price is $2,781 total per night
$2,781 total
Jan 13 - Jan 14, 2026
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
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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
Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes St. Barthelemy
$2,456 nightly
The price is $2,583 total per night
$2,583 total
Jan 20 - Jan 21, 2026
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
VILLA - POOL WITH DIVING VIEWS OVER THE OCEAN

VILLA - POOL WITH DIVING VIEWS OVER THE OCEAN

GUSTAVIA
Get rates
This villa featured laundry facilities and barbecue grills.
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 featuring rocky coastline, a sandy beach and general coastal views

Flamands Beach

4.5/5(6 reviews)

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 which includes landscape views, a bay or harbor and general coastal views

Colombier Beach

4.5/5(5 reviews)

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

Gustavia featuring drinks or beverages, food and cafe scenes
Gustavia showing a bay or harbor and heritage elements
Gustavia
Gustavia featuring general coastal views and a bay or harbor
Gustavia which includes shopping

Frequently asked questions

How much are vacation packages to Leeward?
Get ready to be surprised — you can find yourself in Leeward for only $3,866. 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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