Exclusive Windward Islands Vacation Deals

Windward Islands vacation package deals

Prices and availability subject to change. Additional terms may apply.
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
Jul. 14 - Jul. 21
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
Stay at this 5-star luxury condo in Miami Beach. Enjoy free WiFi, 3 outdoor pools, and 2 restaurants. Popular attractions Lincoln Road Mall and Collins Avenue Shopping Area are located nearby. Discover genuine guest reviews for The Retreat Collection at 1 Hotel & Homes South Beach, in South Beach neighborhood, along with the latest prices and availability – book now.
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
per person
Jul. 5 - Jul. 9
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
Stay at this 5-star luxury hotel in Miami Beach. Enjoy free WiFi, 3 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Lincoln Road Mall and Collins Avenue Shopping Area are located nearby. Discover genuine guest reviews for 1 Hotel South Beach, in South Beach neighborhood, along with the latest prices and availability – book now.
Glendale Hotel

Glendale Hotel

2.5 out of 5
Somerset
Save 100% on your flight
per person
Jun. 2 - Jun. 9
Roundtrip non-stop flight included
Montreal (YUL) to Los Angeles (LAX)
Stay at this hotel in Glendale. Enjoy free WiFi, onsite parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dodger Stadium and Los Angeles Zoo are located nearby. Discover genuine guest reviews for Glendale Hotel, in Somerset neighborhood, along with the latest prices and availability – book now.
Hollywood Inn Suites Hotel

Hollywood Inn Suites Hotel

2.5 out of 5
West Athens
Save 100% on your flight
per person
Jul. 16 - Jul. 22
Roundtrip flight included
Vancouver (YVR) to Los Angeles (LAX)
Stay at this hotel in Gardena. Enjoy free WiFi, onsite parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions SoFi Stadium and Kia Forum are located nearby. Discover genuine guest reviews for Hollywood Inn Suites Hotel, in West Athens neighborhood, along with the latest prices and availability – book now.
Baglioni Hotel Regina - The Leading Hotels of the World

Baglioni Hotel Regina - The Leading Hotels of the World

5 out of 5
Rome City Centre
Save 100% on your flight
per person
Jun. 2 - Jun. 9
Roundtrip non-stop flight included
Montreal (YUL) to Rome (FCO)
Stay at this 5-star luxury hotel in Rome. Enjoy free WiFi, a full-service spa, and breakfast. Popular attractions Spanish Steps and Piazza di Spagna are located nearby. Discover genuine guest reviews for Baglioni Hotel Regina - The Leading Hotels of the World, in Rome City Centre neighborhood, along with the latest prices and availability – book now.
Fontainebleau Las Vegas

Fontainebleau Las Vegas

5 out of 5
Las Vegas Strip
Save 100% on your flight
per person
Jun. 29 - Jul. 6
Roundtrip non-stop flight included
Montreal (YUL) to Las Vegas (LAS)
Stay at this 5-star luxury resort in Las Vegas. Enjoy free WiFi, 7 outdoor pools, and 20 restaurants. Popular attractions Casino at Circus Circus and Stratosphere Tower are located nearby. Discover genuine guest reviews for Fontainebleau Las Vegas, in Las Vegas Strip neighborhood, along with the latest prices and availability – book now.

Frequently asked questions

How much are vacation packages to Windward Islands?
The perfect CA $830 package deal can be booked for your next visit to Windward Islands. Why not let Travelocity take all the hassle out of arranging your travel plans? The great part about bundling your flights and hotel is that it’ll save you a tidy sum. And who wouldn’t love a little extra cash to play with?
Where can I get the best vacation package deals for Windward Islands?
Travelocity will be able to help you snag a terrific Windward Islands package deal. With as many as 400 partner airlines and 665,000 properties across the globe, we know you’ll be able to put together the perfect itinerary.
Why should I book my Windward Islands vacation bundle with Travelocity?
Savings, support and a stress-free booking are just the beginning. Collect lifelong memories and enjoy a fulfilling travel experience knowing you can rely on round-the-clock support. With the Travelocity Price Match Guarantee, you know you’re getting the best deal available.
Can I go on vacation to Windward Islands at this time?
Don’t fly off to Windward Islands without up-to-date facts about quarantine policies and travel restrictions. Travelocity’s Covid-19 Travel Advisor can fill in the blanks. It has all the information you need to make your getaway as stress-free as possible.

Top Windward Islands hotel deals

Coconut Bay Beach Resort & Spa All Inclusive

Coconut Bay Beach Resort & Spa All Inclusive

4 out of 5
Eau Piquant, Vieux Fort
Stay at this 4-star beach property in Vieux Fort. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Sandy Beach and Mankote Mangrove are located nearby. Discover genuine guest reviews for Coconut Bay Beach Resort & Spa All Inclusive along with the latest prices and availability – book now.
Pool
Spa
Sugar Beach, A Viceroy Resort

Sugar Beach, A Viceroy Resort

5 out of 5
Val des Pitons, Soufriere
The price is CA $999 per night
CA $999
per night
May 26 - May 27
Stay at this 5-star luxury resort in Soufriere. Enjoy free WiFi, free parking, and private plunge pools. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Gros Piton and Anse Chastanet Beach are located nearby. Discover genuine guest reviews for Sugar Beach, A Viceroy Resort along with the latest prices and availability – book now.
Pet-friendly
Pool
Jade Mountain Resort

Jade Mountain Resort

5 out of 5
1000 Anse Chastanet Road, Soufriere
Stay at this 5-star luxury resort in Soufriere. Enjoy free WiFi, free parking, and 4 restaurants. Popular attractions Anse Chastanet Beach and Gros Piton are located nearby. Discover genuine guest reviews for Jade Mountain Resort along with the latest prices and availability – book now.
Pool
Spa
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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.