7 deals from our Canadian site*
* Taxes and fees may be additional.
Source: Holland America Line

When the third and fourth guests share the same cabin, the effective per-person price for this cruise drops to $299

Depart Nov. 15; +$50 Nov. 1, 8
Source: CruCon Cruise Outlet

For $525 per person off regular prices, stretch out in a mini-suite while sailing to exotic destinations in the Caribbean and Mexico.

Select December-February dates
Source: Anse Chastanet

Snag some extras at a hotel that was named one of the World's Best by Travel + Leisure in 2014.

July 16 - Nov. 20
Source: iCruise.com

With this deal, score US$200 in onboard credit per cabin and dinner at a specialty restaurant (a total value of US$260).

Sept. 7, 14, 21, 28; +US$50 August dates
Source: American Express Travel

Sail to Key West & Cozumel roundtrip from Ft. Lauderdale onboard Celebrity Constellation.

Depart Nov. 24; +$10 Dec. 8
Thursdays-Mondays through December
Sheraton Santo Domingo
24 deals from our U.S. site*
* Taxes and fees may be additional.

Deals are priced in U.S. dollars and are sourced by our U.S. 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: The Fairmont Southampton

Travel through the end of the year including the Labor Day, Thanksgiving and Christmas holidays.

Aug. 25 - Dec. 31; +$80 July 31 - Aug. 24
Source: Anse Chastanet

Snag $100 in extras at a hotel that was named one of the World's Best by Travel + Leisure in 2014.

July 16 - Nov. 20
Source: Caribbean RumFest

Sample a variety of fine rums in downtown Houston at the Caribbean RumFest. Tickets are 50% off.

Aug. 16 & 17, 2014
Source: Asanda Aveda Spa Lounge

Step up your mani-pedi routine at this "decadent" salon and spa (Time Out New York) and save more than 50% on regular prices.

July 18, 2014 - Oct. 9, 2014
Source: Mangos Caribbean Restaurant

Experience sweet and smoky tastes of the Caribbean with a half-off dinner for two at downtown's Mangos Caribbean Restaurant.

June 27, 2014 - Sept. 25, 2014
Source: Limón

Save 50% on dinner and drinks at Limón, where "modern Peruvian flavors and classical French technique" are blended to create "delicious" fare (Westword).

May 9, 2014 - Sept. 9, 2014
Source: Featured Destination: Puerto Rico

Escape to the Caribbean this summer with increased airlift, including Southwest and United flights

Through August
Source: St. Maarten

Escape to St. Maarten over summer and fall with all-inclusive resorts and oceanfront suites

Deals into December
Source: Puerto Rico

Beachfront hotels, airfare and vacation deals for fall travel

Sept. 1 - Dec. 19
Source: JetBlue Airways

Save on U.S. and Caribbean fares from an award-winning airline

Travel select dates Sept. 16 - Oct. 22
Source: Puerto Rico Tourism Authority

Escape to Puerto Rico where U.S. passports are not required, and save up to 65% off.

Sept. 1 - Dec. 19
September-October; +$10 through August
Westin Dawn Beach Resort & Spa, St. Maarten
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Greg Kunstler — Travel, Entertainment and Local Deal Expert
Greg Kunstler
Deal Expert, Toronto
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