52 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: Holland America Line

Take the whole crew along for a Caribbean cruise with this deal for balcony cabins that sleep four

Nov. 28, 29; Dec. 5, 6, 12, 13
 
Source: Casa de Campo

Conde Nast Traveler readers rated this the No. 1 resort in the Caribbean. Exclusive deal offers daily breakfast and 50% savings.

Travel through August 31
 
Source: Travel by Jen

Hot springs, scenic beaches and rain forests await with this Costa Rica package that includes roundtrip air, hotels, a rental car and daily breakfast

Select May-October departures; +$49 July
 
Source: CheapCaribbean.com

Make a break for Cancun and spend four all-inclusive nights at a newly renovated beachfront resort

Select departures June-November
 
Source: Caribbean Shores Bed & Breakfast

A coastal escape ripe with the natural beauty, Belize earns its place among the world's best-loved tropical havens. This exclusive Travelzoo deal saves members 50% at a cozy bed-and-breakfast near the beach, restaurants and shops.

May 27, 2015 - Dec. 15, 2015
 
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: Princess Cruises

Sail to exotic ports aboard the Regal Princess, the cruise line's newest ship. Many sailings are also available aboard the Royal Princess.

Depart Oct. 24; +$200 November-December dates
 
Source: Cruise.com

Cruise roundtrip from Venice to ports in Montenegro & Greece.

Depart Nov. 14; +$68 Oct. 31
 
Source: Liberty Travel

Depart from San Juan with this cruise that includes stops in St. Thomas, St. Croix, St. John and Castries

Depart: Dec. 12
 
Source: MSC Cruises

Sail roundtrip Miami to Jamaica, the Cayman Islands, Mexico and the Bahamas aboard the sprawling MSC Divina.

Depart June 11, 25; July 9, 23; Aug. 20
 
Source: MSC Cruises

Skip hours of holiday cooking and sail aboard the stunning MSC Divina to ports such as St. Maarten and San Juan over Thanksgiving.

Depart Nov. 21
 
Source: Westin Dawn Beach Resort & Spa

Rejuvenate the mind and body at this oceanfront 4-star hotel

Through October
 
Source: Caribbean Shores Bed & Breakfast

Here's a Travelzoo-exclusive deal on a coastal retreat surrounded by natural beauty, soft sand beaches and rich cultural heritage.

May 28 - Aug. 22 or Oct. 5 - Dec. 15
 
Source: Starwood Hotels and Resorts

Find the ideal vacation in lively Puerto Rico with this sale featuring five popular hotels

Through December
 
Source: Starwood Hotels and Resorts

Discover high savings in the Dominican Republic with this sale featuring three popular hotels

Through December
 
Source: The Westin Grand Cayman Seven Mile Beach Resort & Spa

The resort boasts the largest pool on the island

Most dates August through October
 
Source: CruCon Cruise Outlet

This deal encompasses most major cruise lines and destinations worldwide with exclusive extras.

Select 2015-2016 dates
 
Source: Atlantis, Paradise Island, Bahamas

Travel dates include some weekends and Labor Day weekend, which are rarely discounted.

Travel Aug. 23 - Dec. 17
 
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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