San Juan Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 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
Top hotels in San Juan
Fairfield by Marriott San Jose Airport Alajuela
Radial Francisco J. Orlich Rio Segundo Alajuela
Fully refundableReserve now, pay when you stay
S$134
16 Sept - 17 Sept
includes taxes & fees
9.4/10 Exceptional! (1,177 reviews)
"Everything is great , the staff very friendly 100 %"
Reviewed on 31 Aug, 2026
DoubleTree by Hilton Cariari - San Jose Costa Rica
Autopista Grl. Canas, Cruce San Antonio La Asunción
Fully refundableReserve now, pay when you stay
S$143
6 Sept - 7 Sept
includes taxes & fees
9/10 Wonderful! (1,011 reviews)
"Great place, close to the airport. Clean, full bar and restaurant. Very pretty."
Reviewed on 31 Aug, 2026
Homewood Suites By Hilton Cariari San Jose
Pan American Highway La Asunción Heredia
Fully refundableReserve now, pay when you stay
S$156
6 Sept - 7 Sept
includes taxes & fees
9.6/10 Exceptional! (629 reviews)
"Muy buena ubicación y el personal atento y servicial."
Reviewed on 31 Aug, 2026
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.
What to do in San Juan
Catamaran Ocean King Manuel Antonio
S$109
per adult
90% of travellers recommend
San Jose: Central Market Bites and Sights Walking Tour
S$38
per adult
98% of travellers recommend
San Jose by Night: Small Group Food and Culture Tour with Dinner
S$80
per adult
92% of travellers recommend
Frequently asked questions
What are the cheapest months to go to San Juan?
September, October and November are the best times to search for cheap San Juan holiday packages. Opting to travel in less busy months means you'll typically find lower prices on hotels and flights.
How many days is enough for San Juan?
Usually, a handful of days is enough to check out the main sights during your San Juan holiday. But if you'd like to have time to relax or take day trips, think about extending your itinerary.
How to find the best San Juan package deals?
Start your search for a San Juan package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Amenities," 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, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your San Juan adventure underway.
When to book a holiday package to San Juan?
Secure fantastic discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for a spur-of-the-moment San Juan getaway.
How to plan a trip to San Juan?
- Pick your dates: The things you plan to do in San Juan and your favourite season will help you decide when to go.
- Set your budget: Consider costs like food, flights and transportation when calculating how much to set aside for your trip to San Juan. Then, pick a property that suits your budget, whether that's an affordable option or a more luxurious retreat.
- Decide how long to go away for: Now that you're up to speed on San Juan, you can work out the right length of your holiday. Put together a draft itinerary and give yourself enough time to get through everything on your must-do list.
- Bundle your airfare and accommodation: After you've nailed down your dates and duration, book the perfect San Juan holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
