Leeward Vacation Packages 2026 from $3,125

Leeward flight + hotel vacation packages

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

Tropical Hotel St Barth

Save 100% on your flight

$3,125

per person

Apr 2 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Hotel Manapany

Anse des Cayes

Save 100% on your flight

$3,491

per person

Apr 2 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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

Save 100% on your flight

$6,012

per person

Apr 2 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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

Save 100% on your flight

$4,453

per person

Apr 2 - Apr 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Christopher Hotel

$6,854

per person

Apr 18 - Apr 25

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Top Leeward hotels deals

GYP SEA Saint Barth

Le Colombier St. Barthelemy

$1,191 nightly

$1,250 total

Mar 1 - Mar 2

Total with taxes and fees

Reve de Saint Barth

Les Hauts de Flamands, Merlette St. Barthelemy

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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

Anse des Cayes St. Barthelemy

$1,983 nightly

$2,084 total

Feb 22 - Feb 23

Total with taxes and fees

Hotel Barrière Le Carl Gustaf St Barth

Rue des Normands, Lieu Dit Lurin St. Barthelemy Leeward

$2,670 nightly

$2,804 total

Mar 16 - Mar 17

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

Plage De St. Jean BP1058 St. Barthelemy French West Indies

$951 nightly

$998 total

Feb 17 - Feb 18

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

OPEN FOR NEW YEARS EVE... HOLIDAYS DEC. 28-JAN O3 DEPART...CONTACT ME FOR RATE!!

Anse des Cayes Anse des Cayes

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This villa features an outdoor pool and a hot tub. Laundry facilities and barbecue grills are also provided.

Pool

Hot Tub

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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

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.

Photos of local treasures

Browse Leeward vacation photos for more inspiration

If these walls could talk I have a feeling they would have a lot of stories to tell. This island has quite the history. Named by Christopher Columbus as he passed by in 1492 after his brother, Bartolomeo, the island has been under French, Swedish and French control over the years. It is currently a ‘overseas collectively’ of France and part of the EU.

Dec 2016 - Saint Barth, island of the rich and famous - can also prove beautiful and wild.

Frequently asked questions

How much are vacation packages to Leeward?

Get ready to be surprised — you can find yourself in Leeward for only $3,125. 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.