San Juan Vacations

Book a Hotel + Flight together to unlock savings

Photo by Coby McNaughton

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 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

Find the Best San Juan Vacation Packages

San Juan Hotel Deals

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 SARĀ 459 per night from Jul 30 to Jul 31
SARĀ 459
SARĀ 518 total
30 Jul - 31 Jul
includes taxes & fees
9.2/10 Wonderful! (2,586 reviews)
"I stay at Hilton hotels almost every time across the US and I donā€™t recall ever leaving a bad review. Check in staff not helpful at all. Room was newly renovated and clean, but the door lock didnā€™t work. Had to swipe the card 6 or 7 times for it to open every time. There are 2 small lights in the ..."

Reviewed on 15 July 2026

Hampton by Hilton San Jose Airport
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 SARĀ 387 per night from Aug 10 to Aug 11
SARĀ 387
SARĀ 437 total
10 Aug - 11 Aug
includes taxes & fees
Fairfield by Marriott San Jose Airport Alajuela
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 AsunciĆ³n
Fully refundableReserve now, pay when you stay
The price is SARĀ 460 per night from Aug 6 to Aug 7
SARĀ 460
SARĀ 519 total
6 Aug - 7 Aug
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"The hotel overall was fine for our stay which was to be close to the airport. The reception staff were not very welcoming nor informative but other than that all was ok."

Reviewed on 15 July 2026

DoubleTree by Hilton Cariari - San Jose Costa Rica
See all 1,647 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.

Frequently asked questions

How much does a San Juan vacation package cost?
You'll find cheap prices on Expedia for your San Juan escape. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to San Juan costs.
What are the cheapest months to go to San Juan?
The off-season is the best time to visit San Juan if you're trying to save. Another tip for scoring cheap San Juan vacation packages? Avoid visiting during public holidays and any major festivals.
How to find the best San Juan package deals?
Begin your search for a San Juan package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal San Juan package deal straight 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 getaway off to a flying start.
Is it cheaper to book a San Juan vacation as a package?
You can enjoy significant savings on your next San Juan getaway by booking a tailored vacation package. Check the "Package" heading, then select your destination and travel dates to browse the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to San Juan?
Enjoy fantastic discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment San Juan escape.
How to plan a trip to San Juan?

  1. Choose the best time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to visit San Juan.
  2. Set your budget: Factor in expenses like flights, transportation and food when working out how much to save for your trip to San Juan. Then, pick a property that fits your budget, whether that's an affordable stay or a deluxe getaway.
  3. Decide how long to go away for: Now that you know more about San Juan, you can figure out the ideal length of your break. Create a draft plan and give yourself enough time to cover everything you want to see.
  4. Bundle your airfare and accommodations: Once you've nailed down your travel dates and duration, book the perfect San Juan vacation package for you.