107 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: Jamaica

Escape to the Caribbean with beachfront hotel, air-inclusive vacation and island tour deals

Deals into February
 
Source: CheapCaribbean.com

The formula for an unforgettable trip lies in Jamaica's "white-sand beaches, year-round sunshine, misty mountains, lush rainforest and superb coffee."

Select departures October-March
 
Source: Group IST

Explore Cuba with this unique escorted package that immerses guests in Cubean culture, all while sailing on a three-masted mega-yacht

Select December-March dates
 
Source: Cruises.com

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

Dec. 1; +$20-$27 Nov. 17; Dec. 8
 
Source: Expedia

Book early to save on five-night peak-season stays in what Lonely Planet calls "the deserted Caribbean destination you’ve been looking for".

Select January 2015 dates
 
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

Jan. 19-22
 
Source: Vacation Express

Indulge with this adults-only resort deal, which boasts in-room minibars and oceanview junior suites.

Select November-December departures
 
Source: Liberty Travel

Set sail to the Bahamas aboard Royal Caribbean International's Majesty of the Sea, which features kids activities, Broadway-style entertainment & more

Depart: Oct. 27
 
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: Apple Vacations

Stretch out on the white-sand beaches of Jamaica's Montego Bay with this all-inclusive vacation

Select November departures
 
Source: Expedia

Unwind at a beachfront resort in the sun and escape the chilly weather back home while saving a bundle compared with peak-season stays.

Select December dates
 
Source: Apple Vacations

This adults-only beachfront escape includes $200 in resort coupons, transfers, all meals, drinks and more

Select October-November departures
 
Source: Costa Cruises

Sail roundtrip from Miami to the Bahamas, the Dominican Republic, British Virgin Islands, Leeward Islands and beyond.

Depart Dec. 11
 
Source: Sheraton Old San Juan

This hotel is in the heart of Old San Juan, with the cruise terminals right along the waterfront

Select dates through Dec. 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; +$50 May 10
 
Source: Westin Puntacana Resort & Club

All rooms in this sprawling new resort have balconies and ocean views

Travel through Dec. 19
 
Source: Delta Vacations

Stretch out on a half-mile of white-sand beach and a private island at a resort just minutes away from the airport

Select October-April departures
 
Source: Hilton Rose Hall

The 4-Star Hilton Rose Hall Resort is home to the Caribbean's largest water park.

Select arrivals through March 31
 
Source: British Colonial Hilton Nassau

The resort, according to Fodor's, is a "landmark in the social heart of Nassau."

Select arrivals through January 28
 
Cheap Roundtrip Fares to Montego Bay from:
(Per person, including taxes and fees. Click a price to verify availability now.)
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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