
Caribbean Islands Vacations from $655
Book a Hotel + Flight or Car together to unlock savings
Better together
Find the right fit
Rest easy
Your Caribbean Islands Vacation
Leave the planning up to us with a Caribbean Islands vacation package. With everything arranged before you jet off, the only thing you'll need to do is sit back, relax and enjoy this destination's countless delights. Begin your trip to Caribbean Islands by spending a few nights in Punta Cana, one of the best cities here. When you're ready to stop dreaming and start traveling, Expedia will help turn your Caribbean Islands vacation into a reality.
The Latest Caribbean Islands vacation packages

Oyster Bay Beach Resort
Reviewed on Jul 6, 2025

Simpson Bay Resort, Marina & Spa
Reviewed on Jul 8, 2025

Princess Heights Luxury Boutique Condo Hotel
Reviewed on Jul 4, 2025

Hilton Vacation Club Royal Palm St. Maarten
Reviewed on Jul 8, 2025

Holland House Beach Hotel
Reviewed on Jul 7, 2025
Where to stay in Caribbean Islands

Isla Verde
White-sands, beautifully clear water and excellent water sports make this beach one of the most popular in Puerto Rico.
Discover the most popular places to visit in Caribbean Islands

Port of San Juan
Explore the waterfront in San Juan with a trip to Port of San Juan. Discover the area's top-notch restaurants and its acclaimed art scene.

Eagle Beach
Spot fish swimming in the crystal-clear waters, look for turtle nests on the shore and photograph Aruba’s famous windswept divi-divi trees.

Bavaro Beach
Nothing says vacation like spending a lazy day at Bavaro Beach, a popular beach in Punta Cana. Discover the top-notch restaurants and great live music in this romantic area.
Caribbean Islands Hotel Deals

Reviewed on Jul 6, 2025

Reviewed on Jul 8, 2025

Reviewed on Jul 8, 2025