San Juan Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Find the Best San Juan Vacation Packages
San Juan Hotel Deals
Fairfield by Marriott San Jose Airport Alajuela
Radial Francisco J. Orlich Rio Segundo Alajuela
Fully refundableReserve now, pay when you stay
￥15,902
￥17,970 total
Oct 14 - Oct 15
includes taxes & fees
9.4/10 Exceptional! (1,208 reviews)
"We enjoyed our stay"
Reviewed on Sep 23, 2026
DoubleTree by Hilton Cariari - San Jose Costa Rica
Autopista Grl. Canas, Cruce San Antonio La Asunción
Fully refundableReserve now, pay when you stay
￥14,795
￥16,719 total
Oct 17 - Oct 18
includes taxes & fees
Country Inn & Suites by Radisson, San Jose Aeropuerto, Costa Rica
Sobre Autopista General Cañas Ulloa Heredia
Fully refundableReserve now, pay when you stay
￥12,816
￥14,482 total
Sep 26 - Sep 27
includes taxes & fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
What are the cheapest months to go to San Juan?
September, October and November are the best times to look for cheap San Juan vacation packages. Traveling in less busy periods means you'll typically find better prices on accommodations and flights.
How many days is enough for San Juan?
The ideal length for your San Juan vacation depends on what you'd like to see. Typically, a handful of days to a week will give you time to visit all the top attractions and explore some hidden gems along the way.
How to find the best San Juan package deals?
Start your search for a San Juan package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect San Juan package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your San Juan getaway off to a flying start.
When to book a vacation package to San Juan?
If you've got your San Juan vacation dates confirmed, book as early as you can to snap up some terrific deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for traveling on a whim.
How to plan a trip to San Juan?
- Choose your dates: The things you want to do in San Juan and your favorite season will help you decide when to travel.
- Budget wisely: In addition to the cost of your stay, you should factor in other expenses. These include transportation, flights and food. Also, put aside some extra funds for unexpected costs that could crop up during your trip to San Juan.
- Decide how long to go away for: Now that you're up to speed on San Juan, you can figure out the right length of your break. Put together a rough plan and give yourself enough time to cover everything you want to do.
- Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalized San Juan vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
