Plan a trip to see Windward Islands

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

Ola Boutique Hotel

Condado

$845

per person

Jan 22 - Jan 27

found 1 day ago

Roundtrip flight included

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

18.4/10 Exceptional! (589 reviews)

Very friendly, welcoming and the hotel was clean! We didn’t hear any outside noise and it’s located near everything that we wanted to go.

Reviewed on Nov 18, 2025

Alamanda Cottage at Serenity

Ironshore

$1,150

per person

Jan 25 - Feb 1

found 1 day ago

Roundtrip non-stop flight included

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

No reviews

Ocho Rios Villa at The Palms

$1,179

per person

Jan 25 - Feb 1

found 1 day ago

Roundtrip non-stop flight included

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

20/10 Exceptional! (2 reviews)

Browse tours and tickets to explore Windward Islands

Tours & day trips

See all 488 activities

Soufriere Adventure Cruise with Snorkeling, Lunch & Open Bar

Free cancellation available

Private & custom tours

See all 184 activities

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

Free cancellation available

Water activities

See all 78 activities

Soufriere Adventure Cruise with Snorkeling, Lunch & Open Bar

Free cancellation available

Wildlife & nature

See all 40 activities

Grenada: Half-Day Island Tour with Waterfall Swim Stop

Free cancellation available

Classes & workshops

See all 23 activities

Project Chocolat Bean to Bar Experience from Hotel Chocolat

Free cancellation available

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