San Juan Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 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 Flight + Hotel Deals in San Juan
Price found within the past 48 hours. Click for updated prices.
Taormina Hotel and Casino
Carmen
€1,997
per person
28 Dec - 2 Jan
found 1 day ago
Return direct flight included
St. George's (BDA) to San José (SJO)
8.6/10 Excellent! (998 reviews)
Very friendly Ticas in the bar, large bar downstairs with live music on some nights, good restaurant, good pizza 🍕, best live poker room in Costa Rica, cash available at casino cage on VISA card..... inexpensive, nice hotel rooms ,
genuine Cuban cigars a block away in tobacco store
nos
Reviewed on 10 Oct 2026
Top hotels in San Juan
Country Inn & Suites by Radisson, San Jose Aeropuerto, Costa Rica
Sobre Autopista General Cañas Ulloa Heredia
Fully refundableReserve now, pay when you stay
€86
17 Oct - 18 Oct
includes taxes & fees
8.4/10 Very good! (3,454 reviews)
"Front desk very helpful but the restaurant not professional at all I was more than half of ours nobody came to the table I had to ask for a drink"
Reviewed on 13 Oct 2026
Costa Rica Marriott Hotel Hacienda Belen
700 meters West from Bridgestone/Firest La Asunción Heredia
Fully refundableReserve now, pay when you stay
€162
23 Oct - 24 Oct
includes taxes & fees
Fairfield by Marriott San Jose Airport Alajuela
Radial Francisco J. Orlich Rio Segundo Alajuela
Fully refundableReserve now, pay when you stay
€102
5 Nov - 6 Nov
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 holiday packages. Travelling in less busy periods means you'll typically find better prices on accommodation and flights.
How many days is enough for San Juan?
The ideal length for your San Juan holiday 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 holiday package to San Juan?
If you've got your San Juan holiday 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 travelling 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 favourite 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 personalised San Juan holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
