Leeward Vacation Packages 2026 from $3,466

Leeward flight + hotel vacation packages

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

Christopher Hotel

Pointe Milou

$3,466

per person

Jul 19 - Jul 26

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) 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.

Tropical Hotel St Barth

Saint-Jean

Save 100% on your flight

$3,657

per person

Jul 19 - Jul 26

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) 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

Toiny

Save 100% on your flight

$6,051

per person

Jul 19 - Jul 26

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) 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

Colombier

$4,212

per person

Jul 19 - Jul 26

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) 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.

Hotel Manapany

Anse des Cayes

$5,281

per person

Jul 19 - Jul 26

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) 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.

Top Leeward hotels deals

GYP SEA Saint Barth

Le Colombier St. Barthelemy

$785 nightly

$824 total

May 19 - May 20

Total with taxes and fees

Pool

Breakfast included

Fouquet's Saint-Barth

Rue des Normands, Lieu Dit Lurin St. Barthelemy Leeward

$1,532 nightly

$1,609 total

Jun 12 - Jun 13

Total with taxes and fees

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.

Breakfast included

Spa

Hotel Manapany

Anse des Cayes St. Barthelemy

$1,193 nightly

$1,256 total

Jun 7 - Jun 8

Total with taxes and fees

Pool

Breakfast included

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.

Pool

Breakfast included

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

🏝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.

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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 $3,466. 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.