Plan a trip to see Windward Islands

Price found within the past 48 hours. Click for updated prices.

Ola Boutique Hotel

Condado

per person

Oct 7 - Oct 12

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to San Juan (SJU)

9/10 Wonderful! (429 reviews)

Great place to stay!! Very clean, safe & everything is in walking distance.

Reviewed on Jul 29, 2025

Princess Grand Jamaica Resort - All Inclusive

per person

Oct 8 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)

9/10 Wonderful! (260 reviews)

Hotel is good, not excellent, service around pools was slow, and night activities were not well prepared

Reviewed on Jul 30, 2025

Princess Senses The Mangrove Resort - Adults Only

per person

Sep 29 - Oct 3

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Montego Bay (MBJ)

9.2/10 Wonderful! (236 reviews)

Had a wonderful time ..Denis the( butler ) was amazing

Reviewed on Jul 29, 2025

Browse tours and tickets to explore Windward Islands

Tours & day trips

See all 443 activities

Private Soufriere Experience Tour-Tet Paul Trail, Mud Bath, Waterfall

Free cancellation available

Private & custom tours

See all 169 activities

Private Soufriere Experience Tour-Tet Paul Trail, Mud Bath, Waterfall

Free cancellation available

History & culture

See all 100 activities

Private Soufriere Experience Tour-Tet Paul Trail, Mud Bath, Waterfall

Free cancellation available

Wildlife & nature

See all 39 activities

Dune Buggy Sulphur Spring and Waterfall Experience St. Lucia

Free cancellation available

Classes & workshops

See all 26 activities

Project Chocolat Bean to Bar Experience from Hotel Chocolat

Free cancellation available

Popular places to visit

Falls of Baleine

Commune with nature and explore the great outdoors at Falls of Baleine during your travels in Prospect. Amble around this relaxing area's beautiful beaches and enjoy its top-notch restaurants.

Friendship Bay

Commune with nature and explore the great outdoors at Friendship Bay during your travels in Prospect. Stroll along the beautiful beaches in this relaxing area, or check out its top-notch restaurants.

Bamboo Church

Learn about the local history of Prospect when you take a trip to Bamboo Church. Stroll along the beautiful beaches in this relaxing area, or check out its top-notch restaurants.

Montreal Gardens

Enjoy an outing to Montreal Gardens during your stay in Prospect. Stroll along the beautiful beaches in this relaxing area, or check out its top-notch restaurants.

Botanical Gardens

Explore the great outdoors at Botanical Gardens, a lovely green space in Kingstown. Stroll along the beautiful beaches in this relaxing area, or check out its top-notch restaurants.

Fort Charlotte

Find out about the history of Kingstown when you spend time at Fort Charlotte. Amble around this relaxing area's beautiful beaches and enjoy its top-notch restaurants.