45 deals from our U.S. site*
* Taxes and fees may be additional.
Source: MSC Cruises

Sail aboard MSC Cruises -- a Mediterranean cruise brand with diverse itineraries in the Caribbean, Bahamas and beyond.

Select 2015-2016 dates
 
Source: Aruba

Escape to Aruba with beachfront resort, vacation and flight deals

Deals into December
 
Source: Alamo Rent A Car

Destinations on sale include Mexico, Costa Rica, Argentina, Brazil, Peru, Dominican Republic and Aruba

Through April 30
 
Source: Travel by Jen

Take in the natural wonders of Costa Rica with this vacation package that includes air, hotel stays, daily breakfast and more

Select September-October departures
 
Source: Limón

"Modern Peruvian flavors and classical French technique" are blended to create "delicious" fare at Limón in Uptown (Westword).

Through Oct. 31, 2015
 
Source: Lehman Center for the Performing Arts

Travelzoo members save $20 per ticket on Saturday night Latin music concerts at Lehman Center this summer. Balcony seats are available for three shows.

Saturday, Aug. 8, Aug. 15, Sept. 19, at 8 p.m.
 
Source: Buccament Bay Resort

Take a loved one on a romantic five-night all-inclusive getaway to St. Vincent & the Grenadines in the Caribbean for more than 60% off regular rates.

Options for travel through April 30, 2016
 
Source: MSC Cruises

Bask in the sun and cruise the crystal blue waters of the Caribbean aboard the MSC Divina while saving $260 per person on regular prices.

Depart Dec. 5; +$70 Nov. 28
 
Source: Windstar Cruises

Sail from Bridgetown to exotic Caribbean ports such as Pigeon Island, St. George's and Bequia

Jan. 12, 16
 
Source: MSC Cruises

From Costa Rica to the Caymans, Mexico to St. Maarten, MSC Cruises cover the Caribbean with its distinct style. Snag deals with diverse itineraries.

Select 2015-2016 dates
 
Source: Starwood Hotels and Resorts

Take in the buzz of Puerto Rico, which "pulsates with more life than any other island in the Caribbean" (Frommer's) with 45% off stays at top hotels.

Travel options through December
 
Source: Delta Airlines

Book by July 27 and save on fall travel to Dominican Republic, St. Maarten, Mexico, Panama, Mexico, Costa Rica and Chile

Select dates September-February
 
Source: Princess Cruises

Dive into the aqua water of the Dominican Republic, U.S Virgin Islands and St. Maarten with unlimited drinks. Third and fourth guests sail discounted.

Depart Dec. 11, 20126
 
Source: Princess Cruises

Snag an early bird deal to sail over the Christmas holiday -- the price includes the cabin, all entertainment and meals.

Depart Dec. 23, 2016
 
Source: Regent Seven Seas Cruises

Sail to ports along Mexico, Guatemala, Honduras and Belize aboard the Regent Seven Seas Navigator. Includes all drinks, tips, tours and air.

Depart Dec. 17
 
Source: Cruise.com

Cruise roundtrip from Miami onboard Celebrity Reflection with stops in Puerto Rico, St. Thomas and St. Maarten.

Depart Nov. 28; Dec. 12; +$50 Nov. 14, 21
 
Source: Westin Dawn Beach Resort & Spa

Score 50% off stays through October at this AAA 4-Diamond St. Maarten resort, situated on "one of the island's best beaches" (Fodor's).

Most dates through October 15
 
Source: Norwegian Air Shuttle

Norwegian Air Shuttle is the only airline to offer nonstop flights from NYC to the islands.

January-March
 
Travel options through December
Starwood Hotels and Resorts
 
Aug. 1 - Dec. 18
Hyatt Regency Aruba Resort & Casino
 
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Travelzoo Tips

Anna Heinemann — Travel, Entertainment and Local Deal Expert
Anna Heinemann
Deal Expert, Chicago
So get your travel dates set and start planning early for the best opportunities. More