8 deals from our Canadian site*
* Taxes and fees may be additional.
Source: CruCon Cruise Outlet

Balcony cabins on Royal Caribbean's Harmony, Allure and Oasis of the Seas have been discounted this week for seven-night cruises to the Caribbean.

Select 2016-2017 dates
 
Source: tripcentral.ca

Prices this low with tax for the Eastern Caribbean island of St. Lucia, to a resort of this quality, are extremely rare. Fly with Air Canada Vacations

Select dates from September into late October
 
Source: Disney Cruise Line

Cruise to Castaway Cay, Disney’s private Bahamian paradise and visit Disney World in Orlando.

Select October sailings
 
Source: blu Hotel, St Lucia

This 5-night getaway to St Lucia -- a land of "volcanic rock beaches, lush fruity landscapes, and a lively nightlife" (Frommer's) -- saves 75% on current rates, and includes two spa treatments and US$50 to spend on lunch, dinner or drinks.

Travel options through Dec. 19, 2016 and Jan. 4 - Apr. 30, 2017
87% (91 ratings)
 
Source: Seg'z Restaurant

Savour some classic Canadian-Caribbean dishes from Seg'z Restaurant in Toronto, located North of St. Clair. Travelzoo members dine for half off.

Through Aug. 15, 2016
 
Source: Cruise.com

Sail roundtrip Miami, stopping in St. Thomas, St. Maarten and Barbados

Depart Dec. 11
 
Source: MSC Cruises

This deal includes all meals, drinks, Wi-Fi and a tour excursion. Plus, kids sail free on select sailings.

Depart Oct. 22; +US$50 nearby dates
 
Source: Oceania Cruises

Sail roundtrip Miami to Key West, Cozumel, Costa Maya, Santo Tomas, Roatan, Colon, Puerto Limon and George Town aboard Oceania.

Depart Nov. 17
 
20 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: Atrium Beach Resort and Spa

"St. Martin/Sint Maarten is an exotic rum cocktail of French cuisine, Dutch tolerance and Caribbean relaxation set ... in a sparkling sea of aquamarine" (Frommer's). With this deal, explore this bustling island on a budget.

Travel daily through Nov. 15, 2016
 
Source: blu Hotel, St Lucia

"Magnificent, lush scenery makes Saint Lucia one of the most beautiful Caribbean islands" (Fodor's). Spend five nights discovering its beauty with this deal that saves over 75% on current rates and throws in two 60-minute spa treatments to boot.

Travel options through Dec. 19, 2016 and Jan. 4 - April 30, 2017
 
Source: Hacienda Tamarindo

Named for the 250-year-old tamarind tree that climbs through the center of the lobby, the plantation-style Hacienda Tamarindo in Vieques is "one of the prettiest hotels on the island" (Fodor's).

Arrivals through Dec. 12, 2016
 
Source: Coral Princess Hotel

Reserve a stay at a top 10 San Juan hotel (TripAdvisor) that's great for couples and "feels more like a cozy bed & breakfast" (Oyster.com).

Arrivals through Dec. 12, 2016
 
Source: Holiday Inn Ponce & Tropical Casino

Plan a family vacation to Puerto Rico with a retreat in Ponce, a historic city in the South set amid lush mountains near the Caribbean Sea.

Arrivals through Dec. 12, 2016
 
Source: Westin Resort and Spa Cancun

Plan retreat to sunny Cancun and receive a $100 credit when booking five nights or more with your MasterCard.

Most dates through October; 5 night min.
 
Source: Westin Hotels and Resorts

Save up to 50% off peak season rates with this 4-Star Westin Mexico resort sale into December -- including prime Thanksgiving travel dates.

Travel options through Dec. 20
 
Source: The Westin Grand Cayman Seven Mile Beach Resort & Spa

Save 55% off peak season rates at this luxe Grand Cayman resort, which Frommer's calls "well-managed," "versatile" and "a good family option."

Lowest rates Aug. 14 - Sept. 30
 
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 Nov. 18.

Most dates through Nov. 18
 
Source: Copa Airlines

Fly to 12 cities in nine countries in the Caribbean, Central America and South America.

Aug. 15 - Nov. 16
 
Source: British Virgin Islands Tourism Board

Through Oct. 30
 
Source: Major Airlines on Fly.com

Into October
 

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Greg Kunstler — Travel, Entertainment and Local Deal Expert
Greg Kunstler
Deal Expert, Toronto
Here are some I can no longer live without. More