San Juan Vacations from $705
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 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
The Latest San Juan vacation packages
Price found within the past 48 hours. Click for updated prices.
Dar Lamia Boutique Hotel
Manuel Antonio
$705
per person
Nov 29 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to San José (SJO)
8.6/10 Excellent! (40 reviews)
Don’t book if you are looking for a nice place to stay , if you are ok with mid looking spots than go ahead.To me it had potential to be a beautiful place but they didn’t build it correctly from the start. Things look very poorly built floors are cracked and the pool looked dingy.The staff was nice tho but I didn’t want to eat there type of vibe.
Reviewed on Sep 1, 2026
Way to Heaven Luxury Glamping
$1,308
per person
Nov 29 - Dec 6
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to San José (SJO)
9.6/10 Exceptional! (11 reviews)
10000/10 Javier was a wonderful host, would highly recommend. He was very accommodating, very helpful with local suggestions. We had issues finding the location, he even went to go find us. Absolutely wonderful experience. The dome was one of the coolest experiences we’ve had yet.
Reviewed on Aug 20, 2026
San Juan Hotel Deals
Fairfield by Marriott San Jose Airport Alajuela
Radial Francisco J. Orlich Rio Segundo Alajuela
Fully refundableReserve now, pay when you stay
$101 nightly
$114 total
Oct 5 - Oct 6
Total with taxes and fees
9.4/10 Exceptional! (1,182 reviews)
"Great location. Friendly service."
Reviewed on Sep 12, 2026
DoubleTree by Hilton Cariari - San Jose Costa Rica
Autopista Grl. Canas, Cruce San Antonio La Asunción
Fully refundableReserve now, pay when you stay
$111 nightly
$125 total
Sep 20 - Sep 21
Total with taxes and fees
9/10 Wonderful! (1,006 reviews)
"It was a beautiful place and the staff was so nice and accommodating. Our room was huge. The pool and hot tub was perfect. The shuttle to and from the airport was very helpful . Breakfast was amazing. I really enjoyed my made-to-order omelet."
Reviewed on Sep 13, 2026
Costa Rica Marriott Hotel Hacienda Belen
700 meters West from Bridgestone/Firest La Asunción Heredia
Fully refundableReserve now, pay when you stay
$149 nightly
$168 total
Sep 25 - Sep 26
Total with taxes and 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.
Find the Best San Juan Vacation Packages
More vacations you might like
Frequently asked questions
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 vacation package to San Juan?
If you've got your San Juan vacation 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 traveling on a whim.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
