Caribbean Holidays

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Top destinations in Caribbean

A marina with a white boat named 'Achina' docked, surrounded by palm trees and a building with a green roof.

Punta Cana

Punta Cana
A beach with clear turquoise water, a sandy shore, and a city skyline with tall buildings including a Marriott hotel.

San Juan

San Juan
A pier with kayaks and a sailboat.

Montego Bay

Montego Bay

Top hotels in Caribbean

Hotel El Convento

Hotel El Convento

100 Cristo St San Juan
Fully refundableReserve now, pay when you stay
Rp6.200.561
Rp8.110.369 total
23 Sept - 24 Sept
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"The room looked out to the bay. It’s was clean and quite modern for a historic site. The staff were friendly, professional and very helpful. Cocktail hour was fabulous. Sitting on the patio with the cathedral right across and a"

Reviewed on 18 Sept 2026

Hotel El Convento
British Colonial - Nassau

British Colonial - Nassau

Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
Rp3.537.394
Rp5.336.137 total
23 Sept - 24 Sept
includes taxes & fees
8.6/10 Excellent! (3,058 reviews)
"Always a great stay. Friendly and welcoming staff!!!! Always our first choice! Keep up the great works guys!"

Reviewed on 21 Sept 2026

British Colonial - Nassau
Hotel Rumbao, a Tribute Portfolio Hotel

Hotel Rumbao, a Tribute Portfolio Hotel

100 Brumbaugh Street San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
Rp2.619.583
Rp3.657.311 total
28 Sept - 29 Sept
includes taxes & fees
Hotel Rumbao, a Tribute Portfolio Hotel
See all 88,743 properties in Caribbean
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.

Frequently asked questions

Can I travel to Caribbean right now?
For all the up-to-date facts about visiting Caribbean, take a look at our Covid-19 Travel Advisor. From quarantine policies to travel restrictions and more, Expedia will help make your trip planning as stress-free as possible.
If I'm not able to travel, can I cancel my Caribbean holiday package?
Your situation can change suddenly, so yes, you can. You may be able to change or cancel your Caribbean holiday package for free if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel and rebook, but your car rental company, hotel or airline may charge a fee. Looking for more information? Look up our Customer Service Portal. We'll help make sure your trip goes off without a hitch.
When is the best time of year to visit Caribbean?
There's a real advantage to taking your Caribbean holiday in . You can usually pick up the best deals at this time. , on the other hand, is the most expensive time to visit. If you like the buzz of peak season, head to Caribbean in . The calmer months of will help you avoid the crowds.
How far in advance should I book my Caribbean holiday?
It all depends on the air carrier, but you can usually look up international airfares on Expedia up to a year in advance. While it's advisable to book ahead of time, lucky travellers will occasionally find a cheaper ticket only weeks before the date of departure.
What should I know before booking a Caribbean travel package?
So many places to go, so many things to see and do. With a travel package, you'll be able to afford more of them. Bundle your hotels, rental cars and flights and make big savings.

Stay near popular Caribbean attractions

A beach scene with a flag, beach chairs, umbrellas, and a vendor cart.

Eagle Beach

9.4/10 (6,014 reviews)
Spot fish swimming in the crystal-clear waters, look for turtle nests on the shore and photograph Aruba’s famous windswept divi-divi trees.
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A cruise ship docked near a coastal city with buildings and palm trees.

Port of San Juan

9.0/10 (16,423 reviews)
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 galleries.
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A beach with people walking, clear blue water, and green vegetation in the foreground.

Grace Bay Beach

9.8/10 (5,552 reviews)
Stretch out on fine white sands and marvel at the intense turquoise blue of the Caribbean waters on this pristine and photogenic stretch of shore.
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A coastal resort area with a beach, clear turquoise waters, and a clear sky.

Punta Cana Beach

8.8/10 (30,329 reviews)
Nothing says holiday like spending a lazy day at Punta Cana Beach, a popular beach in Punta Cana. Amble around this relaxing area's seaside and enjoy its lively bars.
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A beach with a lifeguard tower, palm trees, and a clear blue sky.

Luquillo Beach

9.0/10 (3,887 reviews)
Sample local street food or doze under a palm tree on this picturesque stretch of coast.
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A beach with palm trees and turquoise water.

Bavaro Beach

8.8/10 (36,026 reviews)
Nothing says holiday 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.
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A tropical beach with clear turquoise waters, thatched umbrellas, and palm trees.

Mambo Beach

8.8/10 (2,288 reviews)
Nothing says holiday like spending a lazy day at Mambo Beach, a popular beach in Willemstad. Stroll along the seaside or visit the shops in this romantic area.
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Puerto Rico Convention Center

8.8/10 (5,374 reviews)
During your trip, find out what's happening in Puerto Rico Convention Center, a top convention centre in San Juan. Amble around this vibrant area's beautiful beaches or experience its acclaimed art galleries.
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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.