84 deals from our U.S. site*
* Taxes and fees may be additional.
Source: Cayman Islands

Enjoy beautiful beaches, top diving and snorkeling, Stingray City deals

Deals through December
Source: Vacation Express

This trip includes last minute travel dates for those looking for a quick getaway

Select July-September departures
Source: Vacation Express

Unique touches abound at this 4-star hotel, like fresh pastry delivered to your room every morning

Select July-October departures
Source: Vacation Express

Unique touches abound at this 4-star hotel, like fresh pastry delivered to your room every morning

Select July-December departures
Source: CruCon Cruise Outlet

Take in Caribbean vistas complete with swaying palms trees and sun-soaked beaches while sailing for seven nights aboard Norwegian Cruise Line.

Dec. 5; +$20-$200 September-December dates
Source: CruCon Cruise Outlet

This trip is essentially free -- the value of the drinks is more than the cost of the cruise itself.

Depart Nov. 13, 16, 30; Dec. 11; +$20 Nov. 20
Source: CruCon Cruise Outlet

Options aplenty: Choose from three top-rated ships, three departure cities & over a dozen sailings.

2016: Sept. 11, 18, 25; Nov. 6, 13, 27; Dec. 4, 11
Source: Hilton Hotels & Resorts

Save cash on your stay plus snag a $100 resort credit at your choice of Hilton resort

Through September
Source: CruCon Cruise Outlet

Set sail through the exotic islands of the Caribbean with unlimited drinks in hand.

2016: Dec. 11; +$200 Dec. 9; +$350 Nov. 18
Source: CheapCaribbean.com

Spend four nights soaking up the Punta Cana sunshine on this 4-star, all-inclusive getaway

Select September-December departures; more availab
Source: CheapCaribbean.com

Kids stay free at this all-inclusive resort in the Bahamas

July-September departures; more available
Source: Featured Destination: Aruba

Escape to the Caribbean with summer and fall vacations

Select departures through December
Source: Apple Vacations

Steal away to Punta Cana with this last-minute all-inclusive vacation that includes a stay at a Dreams resort

Select dates in July
Source: MSC Cruises

Bask in the sun and cruise the crystal blue waters of the Caribbean aboard the MSC Divina while saving $260 per person on regular prices.

Depart Dec. 5; +$70 Nov. 28
Source: Cruise.com

Sail to ports in the Bahamas, Aruba, Panama & Costa Rica roundtrip from Fort Lauderdale

Depart Dec. 11; +$240 oceanview
Source: Starwood Hotels and Resorts

Take in the buzz of Puerto Rico, which "pulsates with more life than any other island in the Caribbean" (Frommer's) with 45% off stays at top hotels.

Travel options through December
Source: Sheraton Puerto Rico Hotel & Casino

Book with a MasterCard and receive exclusive hotel discounts & extras.

Thurs. - Sat. arrivals, July-Sept.; 3-nt. minimum
Source: Cruise.com

This deal includes one of the following extras: unlimited drinks package, prepaid gratuities or up to $300 onboard credit.

Depart Aug. 30; +$10 Aug. 23
Source: Cruise.com

Cruise roundtrip from Miami onboard Celebrity Reflection with stops in Puerto Rico, St. Thomas and St. Maarten.

Depart Nov. 28; Dec. 12; +$45-$65 Nov. 14, 21
Source: Starwood Hotels and Resorts

This deal offers high savings and long travel windows

Travel options through December
Cheap Roundtrip Fares to Grand Cayman from:
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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