Deals on vacations and trips to Leeward

Save when you book Leeward package deals

Choose two or more items and save on your trip:

Leeward flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Saint-Jean
Save 100% on your flight
Price was $3,803, price is now $2,611 per person
$2,611
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip 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.
Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
Toiny
Save 100% on your flight
Price was $3,760, price is now $2,745 per person
$2,745
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes
Price was $3,834, price is now $3,055 per person
$3,055
per person
Nov 16 - Nov 20
found 14 hours ago
Roundtrip flight included
Miami (MIA) 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
Colombier
Price was $3,119, price is now $2,690 per person
$2,690
per person
Nov 16 - Nov 20
found 14 hours ago
Roundtrip flight included
Miami (MIA) 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.
Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Grand Cul-de-Sac
Price was $4,877, price is now $4,220 per person
$4,220
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Gustavia (SBH)
This smoke-free hotel features a private beach, a full-service spa, and 2 restaurants. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Families will appreciate the playground, onsite laundry facilities, and in-room childcare.

Top Leeward hotels deals

GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Le Colombier St. Barthelemy
Get rates
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
$1,970 nightly
The price is $2,068 total per night
$2,068 total
Oct 29 - Oct 30
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.
Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes St. Barthelemy
$1,526 nightly
The price is $1,600 total per night
$1,600 total
Nov 4 - Nov 5
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.
Pearl Beach Hotel

Pearl Beach Hotel

Plage De St. Jean BP1058 St. Barthelemy French West Indies
$658 nightly
The price is $691 total per night
$691 total
Oct 6 - Oct 7
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.
1493 Boutique Hotel St Barth

1493 Boutique Hotel St Barth

871 Route de Colombier, 97133 Anse des Cayes, Saint Barts St. Barthelemy
Get rates
An outdoor pool, free self parking, and concierge services are featured at this hotel. WiFi in public areas is free. Dry cleaning and luggage storage are also provided.
Don't see what you're looking for?
See all available properties in Leeward
View all properties
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 $2,611. 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.

Explore More Ways to Travel with Travelocity