Cheap Vacations & Vacation Deals to Puerto Rico – Where to book?

by Alyx Sariol  |  Published July 30, 2018

Though small in size, Puerto Rico has plenty to offer as a Caribbean vacation destination. This unincorporated U.S. territory has everything from mountains and waterfalls to beautiful beaches and a historic downtown area. Tourists can experience the culture of Old San Juan or the El Yunque rainforest, with a side trip to an historic fortress or a beach bar.

Puerto Rico has over 250 beaches to choose from (Photo: Ron Reiring via Flickr)

While there are many sites offering cheap vacation packages to Puerto Rico, some are more reputable than others. We’ve compared the top sites based on price, package availability and customer service to highlight the following three. To find the best price on a cheap vacation package to Puerto Rico, we recommend checking your travel dates on all three sites.


We found the largest selection of cheap vacation packages to Puerto Rico on Expedia. You can choose from several destinations on the island, whereas others have listings just in San Juan. Depending on the starting point, Expedia can save travelers anywhere from $150-400 on a travel bundle. To sweeten the deal, some bookings include bonuses like spa credits or free breakfast for two. Travelers can find the most last minute vacation deals to Puerto Rico on Expedia as well. They have the largest selection of properties to choose from, even at the last minute. Expedia’s customer service is available 24/7 to assist with booking and itinerary questions. Most purchases offer free cancelation within 24 hours of booking.

CheapCaribbean has a limited amount of properties listed in Puerto Rico, but is still worth checking for a cheap vacation package. You can easily filter by family-friendly or luxury properties to narrow down the perfect hotel for your stay. Unfortunately, they do not have any all-inclusive properties listed in Puerto Rico on their site so food and drinks would be an additional cost to any package price. If your travel dates are flexible, CheapCaribbean periodically has package deals up to 50% off travel within a certain time period. Book with caution, as many of their deeply discounted deals do not qualify for their general 24-hour cancellation policy.

Apple Vacations

Apple Vacations’ selection of properties in Puerto Rico is also limited, but you can find a cheap vacation package if you are searching well in advance. Their package pricing generally comes in at a higher rate, however, their prices also include roundtrip airport transfers and on-site customer service representatives. They will price match if you find a better rate, so you can still enjoy the added perks that come standard with an Apple Vacations package. They utilize TripAdvisor’s more comprehensive reviews, so we recommend researching a hotel further before booking. Most bookings are subject to a cancellation fee unless you book travel insurance through Apple Vacations.