97 deals from our U.S. site*
* Taxes and fees may be additional.
Source: Puerto Rico

Beachfront hotels, airfare and vacation deals for fall travel

Sept. 1 - Dec. 19
Source: Cayman Islands

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

Deals into December
Source: St. Maarten

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

Deals into December
Source: Hilton Hotels & Resorts

Choose from six resorts located across the island. Many include free breakfast.

Through Dec. 19
Source: Cruise.com

Set sail roundtrip from Fort Lauderdale on board Regal Princess to ports in the Bahamas, St. Thomas & St. Maarten.

Depart Nov. 16, 30; +$50 Dec. 7, 14
Source: Jewel Resorts

Options include a family-friendly hotel where kids stay free, and an adults-only escape loaded with extras. Pricing is per person.

Valid on three-night stays through December.
Source: CheapCaribbean.com

Cash in on a $35 spa credit with this deal.

Select departures Aug. 27 - Sept. 30
Source: Featured Destination: St. Maarten

Escape over summer and fall with all-inclusive resorts and oceanfront suites

Deals into December
Source: CruCon Cruise Outlet

Sail on the Celebrity Constellation, roundtrip Fort Lauderdale with a deal that includes $488 in extras per cabin.

Depart Nov. 19, 2015; +$155 March 12
Source: Discovery Tours by Gate 1

Visit Cuba on an educational journey of Cienfuegos and Havana.

Select April-September dates
Source: CruCon Cruise Outlet

Sail for seven nights aboard the Celebrity Summit, roundtrip Cape Liberty, New Jersey.

Depart May 3, 10; +$100 May 24, 31; Aug. 30, 2015
Source: ClubHotel Riu Bambu

Sip unlimited cocktails at "La Arena" swim-up pool bar after relaxing at the private beach.

Select dates through Dec. 23
Source: Riu Palace Paradise

This Paradise Island hot spot has liquor dispensers and regularly restocked mini-bars in each room.

Select dates Aug. 18 - Dec. 23
Source: Hotel Riu Palace Jamaica

Kick back at a brand new resort in paradise and indulge in unlimited food, drinks and activities.

Select dates into December
Source: Westin Dawn Beach Resort & Spa, St. Maarten

The Westin Dawn Beach Resort & Spa, St. Maarten is on the eastern coast of the island, located on the Dutch side.

Through Dec. 18
Source: Condado Lagoon Villas at Caribe Hilton

Discover Puerto Rico's rich history at the onsite colonial Spanish fort.

Through Dec. 15
Source: Oyster Bay Beach Resort

This beachfront hotel received a TripAdvisor Certificate of Excellence in 2014.

Through Sept.; Oct.-Dec. also on sale
Source: Brac Reef Beach Resort

This all-inclusive vacation is for divers who want a less touristy island base in Cayman.

Through Dec. 15
Source: Radisson Aruba Resort & Casino

Aruba is one of the only Caribbean islands outside the hurricane belt, which means fewer storms.

Select dates thru September; +$16 October-December
Source: Hacienda Tamarindo

Explore picturesque Vieques Islands with an included three-day Jeep rental.

Sept. 1 - Dec. 19
Cheap Roundtrip Fares to Philipsburg from:
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Chris Vassil — Travel, Entertainment and Local Deal Expert
Chris Vassil
Deal Expert, Chicago
Going as a grown-up is just as fun, if not more so, than going at age 6. Here's why. More