119 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: U.S. Virgin Islands

Escape to St. Thomas, St. Croix or St. John and save up to 60%

Deals through December
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: CheapCaribbean.com

Frommer's calls the beaches of Punta Cana "unrivaled in the Caribbean."

Select Aug. 24 - Sept. 30 departures
Source: Hilton Hotels & Resorts

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

Through Dec. 19
Source: Featured Destination: Puerto Rico

Escape to the Caribbean this summer with increased airlift, including Southwest and United flights

Into November
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: Featured Destination: Puerto Rico

No U.S. passport is required

Through December
Source: Westin Dawn Beach Resort & Spa, St. Maarten

The resort sits on "one of the island's best beaches," according to Fodor's.

September-October; +$10 through August
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: Sheraton Old San Juan Hotel & Casino

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

Sundays-Thursdays through Dec. 15
Source: Westin Puntacana Resort & Club

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

Through Nov.
Source: Discovery Tours by Gate 1

Visit Cuba on an educational journey of Cienfuegos and Havana.

Select April-September dates
Source: Delta Vacations

Steal away to the Caribbean with this early booking sale

Feb. 2-5; discounted dates through April 2015
Source: British Colonial Hilton Nassau

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

Select arrivals through Dec. 19
Source: The Westin Grand Cayman Seven Mile Beach Resort & Spa

The resort's pool has plenty of room to splash around, since it is the largest pool on the island.

Aug. 1 - Nov. 23; +$130 Nov. 24 - Dec. 15
Source: Hilton Barbados

This resort is located on Needham's Point, which is among the nicest beaches in Barbados.

Select arrivals August through November
Cheap Roundtrip Fares to Charlotte Amalie from:
(Per person, including taxes and fees. Click a price to verify availability now.)
more cities
close close
don't see your city?
Don’t see your city listed above? Search for flights to Charlotte Amalie:

Still looking for your flight?
Try Fly.com, a new airfare search engine from

Compare Hotel Rates

Travelzoo Tips

Travis Kunz — Travel, Entertainment and Local Deal Expert
Travis Kunz
Deal Expert, Miami
Can you top my tale of meeting the great white? More