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

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

Deals into December
 
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: U.S. Virgin Islands

A U.S. passport is not required to escape to St. Thomas, St. Croix or St. John

Deals through December
 
Source: St. Maarten

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

Deals into 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

Treat yourself to four nights in a room with views of the ocean with this Bahamas vacation.

Most dates Aug. 20 - Dec. 19
 
Source: The Fairmont Southampton

Travel through the end of the year including the Labor Day, Thanksgiving and Christmas holidays.

Aug. 25 - Dec. 31; +$80 July 31 - Aug. 24
 
Source: Vacation Express

Escape to a resort occupying "one of the best strands in the Bahamas" (Frommer's)

Select departures, August-December
 
Source: Anse Chastanet

Snag $100 in extras at a hotel that was named one of the World's Best by Travel + Leisure in 2014.

July 16 - Nov. 20
 
Source: Starwood Hotels & Resorts

Escape to the clear water and sandy beaches of destinations including the Dominican Republic, St. John and Puerto Rico

Select dates Aug. 1 - Dec. 15
 
Source: SmartCruiser.com

Sail to the pink sands of Bermuda in a balcony cabin onboard the Norwegian Breakaway and receive a $200 onboard credit

Select Sept.-Oct. 2015 dates; +$100 April-May
 
Source: Featured Destination: Puerto Rico

No U.S. passport is required

Through December
 
Source: Featured Destination: Cayman Islands

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

Deals into December
 
Source: Expedia

Escape to the Royalton White Sands All Inclusive.

Depart Sept. 2; other departures available
 
Source: MSC Cruises

This deal includes a free upgrade to a higher cabin category, with the possibility of a balcony cabin upgrade.

Depart Sept. 20; +$30-$50 nearby dates
 
Source: Featured Destination: Puerto Rico

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

Through August
 
Source: Featured Destination: U.S. Virgin Islands

A U.S. passport is not required to escape to St. John, St. Croix or St. Thomas

Deals through December
 
Source: BookIt.com

Use the $100 spa credit for pampering at Journeys, the largest full-service spa on the island.

Through Aug. 19
 
Source: Featured Destination: Puerto Rico

No U.S. passport is required

Through December
 
Cheap Roundtrip Fares to Philipsburg from:
(Per person, including taxes and fees. Click a price to verify availability now.)
fly.com
more cities
close close
Don’t see your city listed above? Search for flights to Philipsburg:

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