40 deals from our U.S. site*
* Taxes and fees may be additional.
Source: Holland America Line

With four guests in a cabin, the whole family can cruise for less than $250 per person, effectively.

Select November-December dates
Source: Star Clippers

Feel as if you're on a private yacht as you pull into secluded ports in the Caribbean.

Select departures December-March
Source: Apple Vacations

A massage at a beachfront gazebo, an on-site water park and time along Bavaro Beach are all real possibilities with this Punta Cana vacation package

Select departures through November
Source: IZE Belize

Unlimited excursions and exhilarating activities are the highlight of this package, which includes accommodations, airport transfers and all meals

Aug. 30 - Nov. 15
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: Buccament Bay Resort

At 70% off regular rates, this five-night all-inclusive Caribbean getaway is worth the extra effort. Sneak off to the lush rain forests and idyllic beaches of St. Vincent & the Grenadines -- “the Caribbean's best-kept secret” (Travel + Leisure).

Arrival options through Dec. 15, 2016
86% (84 ratings)
Source: MSC Cruises

Sail aboard MSC Cruises -- a Mediterranean cruise brand with diverse itineraries in the Caribbean, Bahamas and Mediterranean

Select 2016-2017 dates
Source: National Car Rental

Valid on all car categories for rentals of three to five days

Through July 31
Source: Regent Seven Seas Cruises

Sail in a balcony suite to the Bahamas, Puerto Rico, the British Virgin Islands, St. Barts, Antigua, St. Lucia & St. Maarten.

Depart Nov.15
Source: Star Clippers

Sail roundtrip from St. Maarten, stopping in St. Barts, Anguilla, Nevis and Guadeloupe on an intimate yacht

Select November-March dates
Source: Vacations To Go

Sail Roundtrip Port Canaveral to Haiti, Jamaica, Mexico and the Cayman Islands aboard Royal Caribbean's Freedom of the Seas.

July 3
Source: Avoya Travel

Cruise the Caribbean sea on a luxurious Oceania ship and visit Key West, Belize, Cozumel and more

Depart on Dec. 15; others also on sale
Source: Vacations To Go

Sail roundtrip Galveston to Roatan, Belize City and Cozumel aboard Royal Caribbean's Liberty of the Seas.

July 3
Source: Windstar Cruises

This deal combines the lowest price we've seen for a Windstar Cruise with a $150 credit per person.

Select November-April dates
Source: Vacations To Go

Sail roundtrip Fort Lauderdale to St. Maarten, San Juan and Labadee, Haiti.

Depart July 2
Source: Oceania Cruises

Discover exotic islands such as Antigua, Martinique, Barbados, Grenada, St. Lucia and St. Barts

Depart Nov. 5
Source: Copa Airlines

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

Aug. 15 - Nov. 16
Source: Vacation Express

Fly nonstop to the Caribbean and stay at an all-inclusive Barcelo resort

Select dates through August

Compare Hotel Rates