San Juan Holidays

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  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in San Juan

Fairfield by Marriott San Jose Airport Alajuela

Fairfield by Marriott San Jose Airport Alajuela

3.5 out of 5
Radial Francisco J. Orlich Rio Segundo Alajuela
Fully refundableReserve now, pay when you stay
The price is S$136 per night from 24 Aug to 25 Aug
S$136
24 Aug - 25 Aug
includes taxes & fees
Fairfield by Marriott San Jose Airport Alajuela
Hampton by Hilton San Jose Airport

Hampton by Hilton San Jose Airport

3 out of 5
Hwy 1 Airport Blvd Rio Segundo
Fully refundableReserve now, pay when you stay
The price is S$178 per night from 24 Aug to 25 Aug
S$178
24 Aug - 25 Aug
includes taxes & fees
Hampton by Hilton San Jose Airport
DoubleTree by Hilton Cariari - San Jose Costa Rica

DoubleTree by Hilton Cariari - San Jose Costa Rica

5 out of 5
Autopista Grl. Canas, Cruce San Antonio La Asunción
Fully refundableReserve now, pay when you stay
The price is S$171 per night from 26 Aug to 27 Aug
S$171
26 Aug - 27 Aug
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"Felt like a quiet oasis in the city! Beautiful pool, rooms, grounds and lobby! There were some loud travelers around 3 AM but is didn't last long."

Reviewed on 22 Jul, 2026

DoubleTree by Hilton Cariari - San Jose Costa Rica
See all 1,507 properties in San Juan
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

Catamaran Ocean King Manuel Antonio

S$111
per adult
90% of travellers recommend
Catamaran Ocean King Manuel Antonio
San Jose: Central Market Bites and Sights Walking Tour

San Jose: Central Market Bites and Sights Walking Tour

S$38
per adult
98% of travellers recommend
San Jose: Central Market Bites and Sights Walking Tour
ISLA TORTUGA DESDE SAN JOSÉ

ISLA TORTUGA DESDE SAN JOSÉ

S$174
per adult
92% of travellers recommend
ISLA TORTUGA DESDE SAN JOSÉ
See all activities in San Juan

Frequently asked questions

What are the cheapest months to go to San Juan?
To score cheap San Juan holiday packages, organise your trip outside of peak times like public holidays and major festivals. You'll typically find lower prices and better availability in the off-season or when it's less busy.
How many days is enough for San Juan?
The ideal duration for your San Juan holiday depends on what you'd like to do. Typically, a handful of days to a week will give you enough time to tick off all the leading sights and discover some hidden gems along the way.
How to find the best San Juan package deals?
Landing a cheap San Juan package deal is easy with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add a few filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to view the most pocket-friendly San Juan package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
When to book a holiday package to San Juan?
Score fantastic discounts by reserving your flights early with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment San Juan getaway.
How to plan a trip to San Juan?

  1. Pick your dates: What you want to do in San Juan and your favourite season will help you decide when to go.
  2. Figure out your budget: Make sure you have enough money to cover everything from food and transportation to flights and activities. Your hotel will likely be the biggest expense during your trip to San Juan.
  3. Determine how many days away: Start by making a list of all the attractions you want to get to in San Juan. Then, estimate how long you'll need for each, along with any travel time.
  4. Combine your airfare and accommodation: Once you've nailed down your dates and duration, book the right 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.