Windward Islands Vacations from $496

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.
Luxuri Suites

Luxuri Suites

South Beach
Save 100% on your flight
$496
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
6.8/10 (57 reviews)
Ok the fact we had no desk for check was terrible. I could not check in due to a code for door and room acess never being sent to my email resulted in me not checking for 3hours until I was told about a sister property 3 blocks from where I was stay had to walk in the rain to the siater property for thwm to grant me acess codes to get into my room now at 3am. I wouls likw to be reemburst for that night and day. My TV had no working batteries and once I go batteries the TV volum did not work.

Reviewed on Jul 9, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach
$12,114
per person
Oct 17 - Oct 24
found 12 hours ago
Roundtrip flight included
Dallas (DFW) 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

Radio Hotel

Radio Hotel

Manhattan
Save 100% on your flight
$598
per person
Sep 24 - Sep 27
found 2 days ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
8.6/10 Excellent! (2,493 reviews)
Cleanliness isn’t all the way there

Reviewed on Aug 17, 2026

The Link Hotel South Beach

The Link Hotel South Beach

South Beach
$774
per person
Oct 17 - Oct 24
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
9.6/10 Exceptional! (56 reviews)
Things to know: it’s managed by nearby restaurant so it’s important that you check in during certain hours so they can greet you! Loved the location and property

Reviewed on Jul 25, 2026

Don't see what you're looking for?
See all available trips from Columbus to Windward Islands
View all trips

Stay near popular Windward Islands attractions

A lifeguard tower on a beach with turquoise water and a white picket fence.

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.
See properties
A coastal town with colorful houses, a mountain, and a rainbow over the sea.

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.
See properties
A beach at sunset with waves, palm trees, and a silhouette of a person walking.
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.
See properties
A beach with clear turquoise water, boats, and a distant mountain.

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.
See properties
A coastal landscape with a prominent mountain peak, lush green hills, and calm blue waters.

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.
See properties
A beach with clear turquoise water, sandy shore, and a hill with buildings in the background.
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.
See properties

Windward Islands Hotel Deals

Coconut Bay Beach Resort & Spa All Inclusive

Coconut Bay Beach Resort & Spa All Inclusive

Eau Piquant Vieux Fort
9.2/10 Wonderful! (1,118 reviews)
"Very relaxing family vacation"

Reviewed on Aug 15, 2026

Get rates
Coconut Bay Beach Resort & Spa All Inclusive
Siesta Hotel

Siesta Hotel

Morne Rouge Street St. George's
$130 nightly
$142 total
Sep 8 - Sep 9
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
"Hotel is fine, a little outdated, also pricey, but hotel is functional"

Reviewed on Aug 16, 2026

Siesta Hotel
Secrets St. Lucia Resort & Spa All Inclusive Adults Only

Secrets St. Lucia Resort & Spa All Inclusive Adults Only

1 Choc Bay Gros Islet
Fully refundableReserve now, pay when you stay
$599 nightly
$599 total
Sep 8 - Sep 9
Total with taxes and fees
Secrets St. Lucia Resort & Spa All Inclusive Adults Only
See all 6,895 properties in Windward Islands
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.

Find the Best Windward Islands Vacation Packages

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.