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Coconut Bay Beach Resort & Spa on St. Lucia (Figment Designs Miami/Courtesy Coconut Bay Beach Resort & Spa) [enlarge photo] 40 BEST DEALS • U.S. and Canada • Caribbean and Latin America • Europe • Asia, Africa and Middle East • Australia, New Zealand and South Pacific 40 BEST DEALS • Before You Read These Listings...

It pays to book directly with an airline Shop for airfares on meta-search websites like Farecast, SideStep, and Kayak and then book directly with the airline—you'll have more clout in the event that your flight is canceled.

Beyond hotels Looking for an affordable place to stay during the holidays? Consider renting an apartment or even a house. Check out websites like rentalo.com, interhome.us, villasintl.com, vrbo.com, and craigslist.org.

CARIBBEAN

Sun, Sand, Steals
Summer and early fall are the times to snag off-season discounts and deals at Caribbean resorts. Check out these three...

Jamaica from $729
Four nights at the all-inclusive Beaches Sandy Bay in Negril and airport transfers. Price is per room; airfare isn't included. When: Aug. 17–Oct. 31. SS: None. Information: Travel Impressions, 800/284-0044, travelimpressions.com.

St. Lucia from $99
A night's stay at all-inclusive Coconut Bay Beach Resort & Spa is $99 per person, 50 percent off rack rates. Airfare isn't included. When: Aug. 16–Sept. 30. SS: $60. Information: Coconut Bay Beach Resort & Spa, 866/978-6226, cbayresort.com.

Viva Wyndham from $588
Get a fourth night free at any all-inclusive Viva Wyndham. Four nights at the Tangerine in the D.R. starts at $588. Price is per room. When: Until Dec. 31. SS: N/A. Information: Wyndham Hotels & Resorts, 877/999-3223, wyndham.com.

Barbados from $698
Air from Miami; seven nights at the Golden Sands Hotel, across the street from Golden Sands Beach; breakfasts; and a $25 voucher for Oistins Fish Fry. Add from $40 for round-trip transfers or from $350 for a car rental. When: July 1–Sept. 30. Other Gateways: Charlotte ($713); L.A. ($770); Baltimore, Boston, New York, Philadelphia ($795). SS: $350. Information: Atlas Vacations, 800/634-1057, atlasvacations.net.

Jamaica from $527
Spirit Airlines flights from Orlando or Tampa, transfers, and three nights at the all-inclusive Holiday Inn SunSpree Resort Montego Bay. When: July 21–Sept. 29. Other Gateways: Atlanta, Atlantic City, Boston, Chicago, D.C., Detroit, Fort Lauderdale, Myrtle Beach, New York ($554). SS: $196. Information: Spirit Vacations, 800/617-3325, spiritvacations.com.

MEXICO