Windward Islands Vacations from $225
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The Latest Windward Islands vacation packages
Price found within the past 48 hours. Click for updated prices.
Casa Boutique Hotel
South Beach
Save 100% on your flight
Price was $405, price is now $225 per person
$225
per person
May 12 - May 15
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
Rooms were clean and fully stocked, main floor and entry was run down, carpet filthy, no room for your lyggage before 4PM even thought i was told they do. Location was perfect, lady at the front desk was very helpful
Reviewed on Mar 4, 2026
Casablanca Miami Beach
North Beach
Price was $4,251, price is now $1,853 per person
$1,853
per person
Jun 23 - Jun 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
5.8/10 (321 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great.
It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.
Reviewed on Feb 22, 2026
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See all available trips from Columbus to Windward Islands
View all tripsDiscover the most popular places to visit in Windward Islands
Cruise Terminal
Explore the waterfront in Fort-de-France with a trip to Cruise Terminal. While you're in the area, stroll along the beautiful beaches.
Grand Anse Beach
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
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.
Windward Islands Hotel Deals
Royalton Saint Lucia, An Autograph Collection All-Inclusive Resort
Gros Islet Gros Islet
Fully refundableReserve now, pay when you stay
$717 nightly
The price is $717 total per night from Apr 26 to Apr 27
$717 total
Apr 26 - Apr 27
Total with taxes and fees
7.6/10 Good! (1,001 reviews)
Hiiiiii E E E 5 star service but it's hard to book restaurants...staff friendly and helpful. Kids club could be better. Gym excellent. Spa excellent.
Reviewed on Apr 1, 2026
Siesta Hotel
Morne Rouge Street St. George's
$111 nightly
The price is $121 total per night from Apr 7 to Apr 8
$121 total
Apr 7 - Apr 8
Total with taxes and fees
9/10 Wonderful! (1,002 reviews)
Very nice for a quick stay.
Reviewed on Apr 2, 2026
Radisson Grenada Beach Resort
Grand Anse St. George's
Fully refundable
$208 nightly
The price is $227 total per night from May 3 to May 4
$227 total
May 3 - May 4
Total with taxes and fees
8.2/10 Very Good! (1,594 reviews)
Clean room. Very friendly staff. Breakfast was good too.
Reviewed on Apr 2, 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.
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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.