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.
Casablanca Miami Beach
North Beach
CA $8,861
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
5.8/10 (327 reviews)
Valet parking 10/10, safety 10/10 room description not the same as what I got, dirty towels and blanket bad experience.
Reviewed on Aug 12, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $14,577
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) 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
Coconut Bay Beach Resort & Spa All Inclusive
Eau Piquant Vieux Fort
9.2/10 Wonderful! (1,110 reviews)
"Great"
Reviewed on Aug 12, 2026
Siesta Hotel
Morne Rouge Street St. George's
CA $140
CA $168 total
Sep 7 - Sep 8
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 $834
CA $834 total
Sep 8 - Sep 9
includes taxes & fees
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
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.
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.
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 Amir
Morne Rouge Beach
9.0/10 (550 reviews)
Why not spend a carefree afternoon at Morne Rouge Beach during your travels in Grand Anse? Make time to visit the area's shops, or simply enjoy its top-notch restaurants.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
