Windward Islands Vacations from ￥165,569
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The Latest Windward Islands Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Arlo NoMad
Manhattan
Price was ￥1,057,862, price is now ￥547,822 per person
￥547,822
per person
Apr 6 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,831 reviews)
Room was very clean. Staff was amazing, very nice as soon as we walked in. Had a great stay, highly recommend.
Reviewed on Feb 15, 2026
The Muse New York
Manhattan
Price was ￥1,091,264, price is now ￥573,137 per person
￥573,137
per person
Apr 6 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (1,729 reviews)
Perfect location and so close to the theaters! Clean room, friendly staff and perfect bar.
Reviewed on Feb 15, 2026
SIRTAJ - Beverly Hills
South of Wilshire
Save 100% on your flight
Price was ￥345,086, price is now ￥190,922 per person
￥190,922
per person
Apr 27 - May 3
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Los Angeles (LAX)
8.4/10 Very Good! (1,001 reviews)
Excellent location, clean room, comfortable bed
Reviewed on Feb 15, 2026
Hotel Delle Civette
Nomentano
Save 100% on your flight
Price was ￥439,062, price is now ￥252,545 per person
￥252,545
per person
Apr 24 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Rome (FCO)
9.6/10 Exceptional! (267 reviews)
Courteous and helpful staff. Clean, great amenities
Reviewed on Feb 8, 2026
Find the Best Windward Islands Vacation Packages
Windward Islands Hotel Deals
Siesta Hotel
Morne Rouge Street St. George's
The price is ￥15,340 per night from Feb 22 to Feb 23
￥15,340
￥18,408 total
Feb 22 - Feb 23
includes taxes & fees
8.8/10 Excellent! (1,014 reviews)
Everything was great.
Reviewed on Feb 10, 2026
Royalton Saint Lucia, An Autograph Collection All-Inclusive Resort
Gros Islet Gros Islet
Fully refundableReserve now, pay when you stay
The price is ￥83,802 per night from Feb 16 to Feb 17
￥83,802
￥83,802 total
Feb 16 - Feb 17
includes taxes & fees
7.6/10 Good! (1,004 reviews)
The staff was great I felt very welcome.
Reviewed on Feb 12, 2026
Radisson Grenada Beach Resort
Grand Anse St. George's
Fully refundableReserve now, pay when you stay
The price is ￥34,671 per night from Mar 14 to Mar 15
￥34,671
￥41,605 total
Mar 14 - Mar 15
includes taxes & fees
8.2/10 Very Good! (1,560 reviews)
It was a great stay I really only have minor complaints. Let’s start with the good: Beautiful clean property. Excellent customer service by all of the staff. They are very kind and move with urgency and did everything to accommodate my requests. Beautiful property right on the beach with three lovely ...
Reviewed on Feb 13, 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.
Discover the most popular places to visit in Windward Islands
Vigie Beach
4/5(81 reviews)
Join the locals at this city beach where clear waters, white sands and a low-key vibe create a scenic and relaxing experience.
Port of Port Elizabeth
4.5/5(51 reviews)
Explore the waterfront in Pretoria with a trip to Port of Port Elizabeth. Amble around this relaxing area's beautiful beaches and enjoy its top-notch restaurants.
Pigeon Island National Landmark
4.5/5(194 reviews)
Explore the historic British forts for a sense of the fascinating history and climb the two peaks of this headland.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
