Windward Islands Vacations from ￥253,303
Book a Hotel + Flight or Car together to unlock savings
The Latest Windward Islands Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Delle Civette
Nomentano
￥360,438
per person
Sep 21 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Rome (FCO)
9.6/10 Exceptional! (316 reviews)
Staff goes above and beyond to help guests. Every single aspect of the hotel was excellent. We plan to stay there again.
Reviewed on Aug 16, 2026
Harrah’s Las Vegas – A Caesars Rewards Destination
Las Vegas Strip
￥286,202
per person
Nov 9 - Nov 15
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Las Vegas (LAS)
8/10 Very Good! (16,155 reviews)
The room was clean and comfortable. The staff were very pleasant and friendly. I would recommend staying at the hotel to family and friends.
Reviewed on Aug 18, 2026
Find the Best Windward Islands Vacation Packages
Windward Islands Hotel Deals
Coconut Bay Beach Resort & Spa All Inclusive
Eau Piquant Vieux Fort
9.2/10 Wonderful! (1,120 reviews)
"Very friendly staff and a kid friendly. Our room was nice and clean. Good food. Really recommended."
Reviewed on Aug 17, 2026
Siesta Hotel
Morne Rouge Street St. George's
￥10,109
￥12,131 total
Aug 19 - Aug 20
includes taxes & fees
Secrets St. Lucia Resort & Spa All Inclusive Adults Only
1 Choc Bay Gros Islet
Fully refundableReserve now, pay when you stay
￥95,431
￥95,431 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.
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.
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.
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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
