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

No passport required to get to the warm fall temperatures in this island paradise
Through Jan. 2016

Source: Prestige Cruises

The whole family can travel for less than $200 per person? You bet they can.
Oct. 31; Nov. 28; addtl. dates into 2016

Source: Cruises.com

Sail roundtrip Miami to the Bahamas, St. Thomas, Puerto Rico and Turks and Caicos
Nov. 14, 28; +$40 Dec. 12

Source: Cruise.com

Sail roundtrip from Fort Lauderdale to Grand Turk, Puerto Rico, St. Thomas and the Bahamas aboard Holland America ms Westerdam.
Oct. 17, 31; Nov. 14, 28; Dec. 5, 12; +$100 Nov. 7

Source: Expedia

Spend some time on the beaches of Puerto Rico and exploring Old San Juan
September departures; additional available

Source: Regent Seven Seas Cruises

Sail to ports along St. Barts, Antigua, St. Lucia and St. Maarten aboard the Regent Seven Seas Navigator. Includes all drinks, tips, tours and air.
Depart Nov. 12

Source: Hilton Ponce Golf Resort

The Hilton Ponce Golf & Casino offers low Sunday rates for an amenity-rich experience that "appeals to a wide variety of traveler types." (U.S. News)
Sundays through Dec. 20

Source: Multiple Cruise Lines

Leave the cooking to someone else this year, and remember, Santa also visits cruise ships.
Select Thanksgiving, Hanukkah & Christmas dates

Source: The Condado Vanderbilt Hotel

We found the best deal on a 5-star beachfront hotel TripAdvisor users rate #1 in all San Juan.
Travel through Dec. 20

Source: Sheraton Old San Juan

This hotel is in the heart of Old San Juan, with the cruise terminals right along the waterfront.
Through Dec. 15

Source: Wyndham Grand Rio Mar Beach Resort and Spa

Stay four nights or longer and get a credit to use on food and drinks.
Through Dec. 22

Source: Condado Plaza Hilton

This Hilton is the "island's only luxury hotel with both Atlantic and lagoon views" (Fodor's).
Oct. 1 - Dec. 15

Source: El Conquistador Resort & Waldorf Astoria Spa

This top-rated Waldorf Astoria resort is home to the only water park in Puerto Rico.
Through Dec. 23

Source: TRYP by Wyndham Isla Verde

The hotel is eight miles away from a 16th-century citadel, Fort San Felipe del Morro.
Nov. 1 - April 30

Source: Hotel Villa Cofresi

Rincón is the surfing capital of Puerto Rico.
Sunday-Thursday, Oct. 1 - Dec. 10

Source: Verdanza Hotel

Soak up the sun at nearby Isla Verde Beach and snag some free extras.
Sundays-Thursdays through Dec. 23; Jan. 4-14

Source: Courtyard by Marriott San Juan Miramar

Isla Grande Airport is in Miramar; here you can board flights to the islands of Vieques and Culebra.
Oct. 1-31

Source: InterContinental San Juan

Our Deal Experts who stayed here praised the top-notch service and the swim-up bar.
Select dates through Dec. 16

Cheap Roundtrip Fares to San Juan from:
(Per person, including taxes and fees. Click a price to verify availability now.)
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Travelzoo Tips

Haifa Sweeny — Travel, Entertainment and Local Deal Expert
Haifa Sweeny
Deal Expert, San Francisco
There are still plenty of great fares if you're strategic about finding them. More