13 deals from our U.S. site*
* Taxes and fees may be additional.
Source: CheapCaribbean.com

Dash off to a 4-star Waldorf-Astoria Resort in Puerto Rico -- no passport required

Select dates September-November
 
Source: Online Vacation Center

Sail in a balcony cabin aboard Oceania Cruises with a deal that offers prepaid gratuities, $200 in onboard credit per cabin and stops in exotic ports.

Dec. 12; +$600-$1100 December-February dates
 
Source: Doraku Brickell

Live jazz animates Mary Brickell Village for a night of four-course dining and unlimited drinks.

Friday, Sept. 18, 2015
 
Source: Buccament Bay Resort

At more than 60% off regular rates, this five-night all-inclusive Caribbean getaway is worth the extra effort. Sneak off to the lush rain forests and volcanic black-sand beaches of St. Vincent & the Grenadines, “an under-the-radar getaway for the jet-setting elite” (Travel + Leisure).

Options for travel through April 30, 2016
 
Source: Sheraton Puerto Rico Hotel & Casino

Try your luck at Puerto Rico's largest casino and save 50% off peak season rates through November at this 4-star San Juan hotel and casino.

Thur. - Sat. arrivals thru Nov. 28.; 3-nt. minimum
 
Source: W Retreat & Spa - Vieques Island

Visit one of the "Top 10 Islands in the Caribbean & Atlantic" (Conde Nast Traveler) and save 40% off peak season rates on stays through October.

Most dates August-October; 3-nt. minimum
 
Source: Hotwire.com

Snag a low daily rate in San Diego, Miami, Puerto Rico, Phoenix & more

Next four weeks
 
Source: MSC Cruises

Sail roundtrip Miami aboard the MSC Divina to the U.S. Virgin Islands, Puerto Rico and the Bahamas.

Depart Dec. 19
 
Source: Holland America Line

With four guests in a cabin, take the whole family on a seven-night cruise for only $225 per person

Oct. 17, 31; Nov. 7, 14; other dates through 2016
 
 
Into November
Major Airlines on Fly.com
 
Through 2015
Travelzoo
 
 
1 deal from our Canadian site*
* Taxes and fees may be additional.

Deals are priced in Canadian dollars and are sourced by our Canadian Deal Experts. Airfare and air-inclusive vacation or cruise pricing includes taxes; hotel, entertainment, car rental, cruise and Local Deal prices do not include tax, and you may need to pay some tax directly to the provider.

Source: Buccament Bay Resort

At more than 60% off regular rates, this five-night all-inclusive Caribbean getaway is worth the extra effort. Sneak off to the lush rain forests and volcanic black-sand beaches of St. Vincent & the Grenadines, “an under-the-radar getaway for the jet-setting elite” (Travel + Leisure).

Options for travel through April 30, 2016
 

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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