Windward Islands Vacation Packages
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Top Windward Islands Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Virgin Hotel Las Vegas, Curio Collection by Hilton
CA $431
per person
Nov 22 - Nov 26
found 2 days ago
Roundtrip non-stop flight included
Vancouver (YVR) to Las Vegas (LAS)
9/10 Wonderful! (8,786 reviews)
Room was spacious and modern. However walls are thin and you can hear the people next door coughing. Room amenities not well maintained (the ironing board I had could barely be brought up to full height). Opal tower is a 5 min walk from lobby and not convenient. Rideshare stand also not convenient
Reviewed on Oct 2, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $12,421
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
Ready to book your vacation to Windward Islands?
Windward Islands Hotel Deals
Siesta Hotel
Morne Rouge Street St. George's
CA $75
CA $90 total
Oct 7 - Oct 8
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Lovely views, warm staff"
Reviewed on Sep 28, 2026
Secrets St. Lucia Resort & Spa All Inclusive Adults Only
1 Choc Bay Gros Islet
Fully refundableReserve now, pay when you stay
CA $1,136
CA $1,136 total
Oct 3 - Oct 4
includes taxes & fees
Coconut Bay Beach Resort & Spa All Inclusive
Eau Piquant Vieux Fort
9.2/10 Wonderful! (1,169 reviews)
"Friendly staff"
Reviewed on Sep 30, 2026
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.
Stay near popular Windward Islands attractions
Photo by Catherine Carroll
Grand Anse Beach
9.6/10 (1,447 reviews)
If a restful vacation is part of your travel plans, Grand Anse Beach might be the perfect place to seek out during your trip to Grand Anse. Make time to visit the area's shops, or simply enjoy its top-notch restaurants.
Gros Piton
9.6/10 (803 reviews)
Explore one of the most famous sites in Soufrière, a gigantic volcanic peak rising from the sea that attracts visitors from all over the world.
Reduit Beach
9.0/10 (1,288 reviews)
Ride a Jet Ski, laze on the sand and enjoy a cool drink at the bar on this scenic beach set against a backdrop of verdant hills.
Anse Chastanet Beach
9.2/10 (538 reviews)
Enjoy a pleasant Caribbean beach day surrounded by abundant natural beauty. Relax sunbathing on dark sand and snorkeling in crystal-clear waters.
Photo by Davz
Sandy Beach
7.8/10 (211 reviews)
If a restful vacation is part of your travel plans, Sandy Beach might be the perfect place to seek out during your trip to Vieux Fort. While in this romantic area, you can savor the top-notch restaurants.
Marigot Bay
8.8/10 (598 reviews)
Commune with nature and explore the great outdoors at Marigot Bay during your travels in Marigot Bay. While in this relaxing area, you can savor the top-notch restaurants.
Pointe du Bout Beach
8.4/10 (376 reviews)
If a restful vacation is part of your travel plans, Pointe du Bout Beach might be the perfect place to seek out during your trip to Pointe du Bout.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
