122 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: Aruba

Beachfront resorts, vacations, cruises & flights

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: Venetian Ridge Vacation Villas + Spa

Stretch out in a spacious two-bedroom villa and sip on some complimentary welcome drinks.

Through Dec. 23
 
Source: Friendly Planet Travel

Long a mystery, Cuba's culture, music, arts and community reveal themselves during this U.S. government approved tour that saves $1390 per person.

Select November-April dates
 
Source: Grand Palladium Jamaica Resort & Spa

This is the lowest price we've seen for an all-inclusive Jamaica resort all year

Sept. 17 - Dec. 21; +$120 Dec. 22-31
 
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, 23; +$5-$50 Nov. 9, 30; Dec. 7, 14
 
Source: Expedia

Lonely Planet says "this tropical dream is the deserted Caribbean destination you’ve been looking for". Fly roundtrip for seven nights.

Select October dates
 
Source: Cruises.com

Sail on the Majesty of the Seas with stops in Nassau, Key West and CocoCay

Sept. 22; +$34-$45 Sept. 29; Oct. 13
 
Source: Liberty Travel

Steal away to the Bahamas with this four-night vacation package that includes air, hotel transfers and extras; kids 11 & under stay and play free

Nov. 3-6
 
Source: Cruises.com

Sail on Royal Caribbean from Fort Lauderdale, making stops in Key West and Grand Cayman

Sept. 20; +$69 Oct. 18
 
Source: Expedia

Jet to Montego Bay, where a weeklong vacation of sun, sea, sand, dining and cocktails awaits.

Select October dates
 
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: American Express Travel

Sail onboard Norwegian Breakaway roundtrip from New York City with stops in Port Canaveral and Nassau.

Depart May 30; +$40 May 2, 9; +$140 April 24
 
Source: Cruise.com

Sail to the pink sands of Bermuda onboard Celebrity Cruises and receive prepaid gratuities and a choice of classic beverage package or $200 credit

Depart May 3, 10; +$45 May 17
 
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: Expedia

Includes nonstop weekend flights to the U.S. Virgin Islands and accommodations at a family-friendly hotel.

Select October dates
 
Source: Cruises.com

Cruise on the Allure of the Seas and make stops in Cozumel, Labadee and Falmouth

Nov. 29, 30; +$21-$62 Nov. 6, 16; Feb. 21
 
Source: Featured Destination: Aruba

Escape to the Caribbean with an island-wide sale in Aruba

Deals through December
 
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.
 
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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