56 deals from our U.S. site*
* Taxes and fees may be additional.
Source: Discovery Tours by Gate 1

Escape to another place and time in Cuba, noted for its pristine beaches, vintage cars and vibrant city life that pulses to the beat of the timba.

Select July-August departures
Source: CheapCaribbean.com

Kick back on one of the best beaches in Jamaica with this all-inclusive special; upgrades to the Grand Palladium Lady Hamilton are also on sale

Select departures February-July
Source: CheapCaribbean.com

Sun-drenched beaches and 4-star treatment are the perfect cure for winter blues.

February-June departures
Source: Sandals Barbados

The grand opening of Sandals Barbados -- fresh off a $65 million renovation -- is one of the reasons Barbados made this year's Fodor's Go List.

May 19 - Aug. 19; +$28 March 28 - April 15
Source: Funjet Vacations

Spend three days in Jamaica with this all-inclusive escape at a beachfront resort

Feb. 1, 5, 9, 19, 22-23
Source: Cruise.com

Sail to Haiti, Jamaica, Cozumel and the Cayman Islands onboard Royal Caribbean's Freedom of the Seas.

Depart Feb. 15; April 12; +$20 March 1
Source: JetBlue Getaways

Includes stay at adults-only Papagayo Beach Hotel

Valid select dates in February and March
Source: Sheraton Old San Juan

This hotel is in the heart of Old San Juan, with the cruise terminals right along the waterfront.

Select Sundays-Thursdays through March
Source: Cruise.com

Sail to the pink sands of Bermuda onboard Celebrity Cruises and receive prepaid gratuities and a choice of classic beverage package or $200 credit

Depart May 10; +$50 May 3
Source: BookIt.com

Trade snow for sun with an all-inclusive resort sale packed with extras.

Travel select dates through 2015
Source: Delta Vacations

Includes roundtrip air, ground transfers and extra perks at a 4-star hotel

Priced for April; more departures available
Source: BookIt.com

With this deal, book a flight + hotel package for four nights or longer and score a $300 flight credit.

Through June
Source: CheapCaribbean.com

Save over $600 on this romantic beachside vacation including airfare and all meals

January-July departures
Source: Sheraton Puerto Rico Hotel & Casino

Great for business or leisure, the hotel is near both the convention center and Condado Beach

Select weekdays through March
Source: Regent Seven Seas Cruises

This deal includes prepaid gratuities, unlimited shore excursions, unlimited drinks, transfers, a hotel stay & cruise through exotic Caribbean ports.

Depart March 8
Source: The Condado Plaza Hilton

Bordered by both the beach and the lagoon, the resort is surrounded by rich marine life.

Select dates through April 28
Source: Southwest Airlines Vacations

Save $650 with this three night Punta Cana vacation package

Feb. 2-4, 8-10, 16-17
Select dates February-May
Major Airlines on Fly.com
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Travelzoo Tips

Hilary Solan — Travel, Entertainment and Local Deal Expert
Hilary Solan
Deal Expert, Chicago
Several hotel chains, including Hilton and Choice Hotels, offer discounts for active More