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129337 Travelers rated Caribbean highly for Beaches and Islands

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Book a package and join the 188 others who’ve received 100% off their flights this year!
Book a package and join the 188 others who’ve received 100% off their flights this year!
Book a package and join the 188 others who’ve received 100% off their flights this year!

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Featured Caribbean Flight + Hotel packages

2 to 5 night packages to Caribbean

Top Rated Caribbean Hotels

Estimated price for 1 night/2 adults

Hotel El Convento
Hotel El Convento
4.5 out of 5.0 100 Cristo St, San Juan
Free Cancellation
$238
4.6/5 (183 reviews)

We enjoyed our stay very much especially the daily wine and cheese.

Reviewed on Feb 17, 2019
The Reef at Atlantis, Autograph Collection
The Reef at Atlantis, Autograph Collection
4.5 out of 5.0 Paradise Beach Drive, Paradise Island, New Providence
Get Rates
4.3/5 (103 reviews)

Clean, quiet, poor foods in the grocery of Reef; regularity of the shuttles

Reviewed on Mar 18, 2019
Boutique Hotel Palacio
Boutique Hotel Palacio
3.5 out of 5.0 Calle Duarte 106, Santo Domingo, Distrito Nacional
Free Cancellation
$77
4.3/5 (53 reviews)

Had an excellent experience and I definitely be back on my next vacation

Reviewed on Feb 6, 2019
British Colonial Hilton - Nassau
British Colonial Hilton - Nassau
4.0 out of 5.0 Number One Bay St, Nassau, New Providence
Free Cancellation
$230
4.0/5 (128 reviews)

I like everything about the property nice nice nice nice

Reviewed on Apr 15, 2019
Sheraton Old San Juan Hotel
Sheraton Old San Juan Hotel
4.0 out of 5.0 100 Brumbaugh Street, San Juan
Free Cancellation
$164
3.9/5 (491 reviews)

Great location to see Old San Juan, great staff, nice facility.

Reviewed on Apr 18, 2019
Hotel Plaza De Armas Old San Juan
Hotel Plaza De Armas Old San Juan
2.0 out of 5.0 Viejo San Juan, San Jose St, 202, Btw San Francisco St and Fortaleza, San Juan
Free Cancellation
$86
3.4/5 (52 reviews)

Nice, classic hotel in Old San Juan overlooking Plaza de Armas and within walking distance to numerous restaurants and bars...and the water. Excellent cortaos and good breakfast at the cafe in the lobby. FYI The area was a bit loud in the am with normal activity (garbage trucks, construction ...

Reviewed on Feb 6, 2019

Cheap Caribbean Hotels

Estimated price for 1 night/2 adults

Comfort Suites Paradise Island
Comfort Suites Paradise Island
4.0 out of 5.0 Paradise Island Drive, Paradise Island, New Providence
$251
3.8/5 (604 reviews)

It was well maintained around the grounds, but there was one very large coackroach in the room that nearly gave my girlfriend a heart attack.

Reviewed on Apr 9, 2019
BudgetBreakfastPool
Breezes Resort Bahamas All Inclusive
Breezes Resort Bahamas All Inclusive
3.0 out of 5.0 West Bay Street, Cable Beach, Nassau, New Providence
$232
3.5/5 (533 reviews)

We had always had a room with two double beds and a roll away for 3 adults in our past visits. They did not want to give us a roll-away (even though it was stated in our notes). We finally got one.

Reviewed on Apr 19, 2019
BudgetBeachPool
Coral by the Sea Hotel
Coral by the Sea Hotel
1.5 out of 5.0 Calle Rosa 2, Carolina
Free Cancellation
$99
2.8/5 (164 reviews)

The staff was amazing. Very helpful and eager to please you. The hotel is clean and conveniently located. There are 2 restaurants adjacent to the hotel with entrances right from the lobby which are excellent. I truly enjoyed my stay. :)

Reviewed on Oct 24, 2018
BudgetDiningBeach

Best time to take a vacation to Caribbean

The Caribbean features a tropical climate with sunshine year-round, making a Caribbean vacation worthwhile no matter what time of the year. The region experiences dry and wet seasons, plus much warmer months, so the best time to visit boils down to whether you prefer perfect weather or lower hotel rates.

January to May tend to be drier months, and are more popular with travelers -- especially in January. From early spring through summer, more rain and hotter temperatures (plus cool trade winds) make this an ideal time to find great deals on a Caribbean vacation. Hurricane season officially spans from June through November, and early December is the best time to go for low hotel rates and few crowds.

Insider tips for Caribbean travel

Do the Dolphin Cay Deep Water Swim at Atlantis

Do the Dolphin Cay Deep Water Swim at Atlantis and snorkel alongside a dolphin using your own water scooter.

Try The Fish Fry restaurant in Nassau

Try The Fish Fry restaurant in Nassau near Arawak Cay for authentic Bahamian conch salad, fried fish and cold Kalik beer.

Buy some bling in St. Martin

Buy some bling in St. Martin, where you’ll find some of the best deals on silver and gold in all of the duty-free Caribbean.

Rent a scooter in Bermuda

Rent a scooter in Bermuda for great exploration, with stops in Dockyard, Hamilton City, St. George and the famous Swizzel Inn.

Eat at Scotchie’s in Montego Bay and Ocho Rios

Eat at Scotchie’s in Montego Bay and Ocho Rios for fantastic Jamaican jerk food, plus traditional fried dough and breadfruit.

*Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2018 to December 31, 2018 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.

* Prices reflect the lowest "base rate" found over the next 30 days. Rates are subject to change and may not include taxes and fees, hotel service charges, extra person charges, or incidentals, such as room service. All rates are displayed in USD unless otherwise noted. Converted rates are provided for your convenience. They are based on today's exchange rate, but the hotel will charge you in the local currency.