San Juan Vacations

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Find the Best San Juan Vacation Packages

San Juan Hotel Deals

Fairfield by Marriott San Jose Airport Alajuela

Fairfield by Marriott San Jose Airport Alajuela

Radial Francisco J. Orlich Rio Segundo Alajuela
Fully refundableReserve now, pay when you stay
AED 342
AED 386 total
16 Sep - 17 Sep
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

Autopista Grl. Canas, Cruce San Antonio La Asunción
Fully refundableReserve now, pay when you stay
AED 364
AED 412 total
4 Sep - 5 Sep
includes taxes & fees
9/10 Wonderful! (1,009 reviews)
"Todo muy lindo y limpio, el personal muy atentos..."

Reviewed on 29 August 2026

DoubleTree by Hilton Cariari - San Jose Costa Rica
Homewood Suites By Hilton Cariari San Jose

Homewood Suites By Hilton Cariari San Jose

Pan American Highway La Asunción Heredia
Fully refundableReserve now, pay when you stay
AED 398
AED 450 total
4 Sep - 5 Sep
includes taxes & fees
9.6/10 Exceptional! (623 reviews)
"Clean"

Reviewed on 29 August 2026

Homewood Suites By Hilton Cariari San Jose
See all 914 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 season, choice of hotel and length of stay will influence how much your vacation to San Juan costs.
What are the cheapest months to go to San Juan?
You can typically find lower rates and greater availability in September, October and November. Browse our cheap San Juan vacation packages and you could get some great off-season discounts.
How to find the best San Juan package deals?
Use Expedia's filter tool to help you find some of the best San Juan package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for San Juan package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a San Juan vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component individually. And you'll still enjoy the freedom to create a customized San Juan vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to San Juan?
If you have your San Juan travel dates confirmed, book as early as you can to snap up some unbeatable deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are great for traveling on a whim.
How to plan a trip to San Juan?
  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to go to San Juan.
  2. Plan your budget wisely: In addition to the cost of your hotel, you'll need to consider other expenses too. These include food, transportation and flights. Also, put aside a little extra for unexpected costs that may come up during your trip to San Juan.
  3. Decide how many days away: Start by listing all the activities and sights you'd like to experience in San Juan. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to find a San Juan vacation package that brings all your bookings together.

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