Windward Islands Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
Top Windward Islands Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Reserve at Park MGM
Las Vegas Strip
CA $910
per person
Oct 27 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Las Vegas (LAS)
9.2/10 Wonderful! (809 reviews)
LOVED this place - well done! The only negative was the concert going on below our room that was CRAZY loud (even though it was indoors)
Reviewed on Sep 21, 2026
Ready to book your vacation to Windward Islands?
Windward Islands Hotel Deals
Siesta Hotel
Morne Rouge Street St. George's
CA $115
CA $138 total
Sep 30 - Oct 1
includes taxes & fees
Secrets St. Lucia Resort & Spa All Inclusive Adults Only
1 Choc Bay Gros Islet
Fully refundableReserve now, pay when you stay
CA $847
CA $847 total
Sep 28 - Sep 29
includes taxes & fees
Coconut Bay Beach Resort & Spa All Inclusive
Eau Piquant Vieux Fort
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.
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.
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.
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.
Photo by Nerdin St Rose
Rodney Bay Marina
8.8/10 (1,500 reviews)
Explore the waterfront in Gros Islet with a trip to Rodney Bay Marina. Stroll along the beautiful beaches or visit the shops in this relaxing area.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
