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San Juan Vacations from $1,400
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The Latest San Juan Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Way to Heaven Luxury Glamping
Dec 28 - Jan 2Way to Heaven Luxury Glamping + Flight
Monteverde5 nights2.0 star property9.6/10 - Exceptional (12 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 August 20, 2026Roundtrip • Miami (MIA) - San José (SJO)MIA - SJO • Nonstop SJO - MIA • 1 stop - Fondavela Hotel
Jan 4 - Jan 8Fondavela Hotel + Flight
Monteverde4 nights4.5 star property8.6/10 - Excellent (416 reviews)Roundtrip • Boston (BOS) - San José (SJO)BOS - SJO • 1 stop SJO - BOS • 2 stops$11,685$1,455found 1 day agoper traveler - The Springs Resort and Spa at Arenal
Jan 23 - Jan 28The Springs Resort and Spa at Arenal + Flight
Monterrey5 nights5.0 star property9.8/10 - Exceptional (1,005 reviews)"Wonderful staff throughout!"Reviewed November 7, 2026Roundtrip • Boston (BOS) - San José (SJO)BOS - SJO • 1 stop SJO - BOS • 1 stop$3,891$2,178found 1 day agoper traveler - Gaia Hotel And Reserve - Adults Only
Jan 23 - Jan 28Gaia Hotel And Reserve - Adults Only + Flight
Manuel Antonio5 nights4.5 star property9.6/10 - Exceptional (544 reviews)"Excelente atención y el hotel es muy hermoso y bien ubicado"Reviewed October 19, 2026Roundtrip • Boston (BOS) - San José (SJO)BOS - SJO • 1 stop SJO - BOS • 1 stop$3,743$2,236found 1 day agoper traveler - Finca Sunset Monteverde
Dec 27 - Jan 1Finca Sunset Monteverde + Flight
Monteverde5 nights2.0 star property9.8/10 - Exceptional (70 reviews)"No words I can write could ever do this place justice. The views are unbelievable and the amenities in the room go above and beyond expectations! There were umbrellas, card games, a telescope for looking at the stars, an outside lounge net, a hot tub on the balcony, and even the shower had a window with an amazing view! Alex was so welcoming and friendly! He recommended the best dining spots and brought us on a night-walking tour and a guided tour of the Monteverde Hanging Bridges!"Reviewed October 6, 2026Roundtrip • Boston (BOS) - San José (SJO)BOS - LIR • Nonstop LIR - BOS • Nonstop
San Juan Hotel Deals
9.2 out of 10, Wonderful, (960 reviews)
9.2/10
Wonderful
(960 reviews)
$131 nightly
The price is $147
$147 total
Nov 13 - Nov 14
Total with taxes and fees
9.2 out of 10, Wonderful, (1,001 reviews)
9.2/10
Wonderful
(1,001 reviews)
"The have a good location and very close to downtown."
$64 nightly
The price is $72
$72 total
Dec 8 - Dec 9
Total with taxes and fees
Holiday Inn San Jose La Sabana by IHG
Holiday Inn San Jose La Sabana by IHG3.5 star property
7.3 mi from San Juan
9.2 out of 10, Wonderful, (374 reviews)
9.2/10
Wonderful
(374 reviews)
"Tener mini fridge en la habitación"
$122 nightly
The price is $138
$138 total
Nov 22 - Nov 23
Total with taxes and fees
Courtyard by Marriott San Jose Escazu
Courtyard by Marriott San Jose Escazu3.5 star property
9.5 mi from San Juan
9.0 out of 10, Wonderful, (953 reviews)
9.0/10
Wonderful
(953 reviews)
$130 nightly
The price is $147
$147 total
Nov 20 - Nov 21
Total with taxes and fees
Residence Inn by Marriott San Jose Escazu
Residence Inn by Marriott San Jose Escazu3.5 star property
9.2 mi from San Juan
9.4 out of 10, Exceptional, (803 reviews)
9.4/10
Exceptional
(803 reviews)
$147 nightly
The price is $166
$166 total
Nov 20 - Nov 21
Total with taxes and fees
8.4 out of 10, Very good, (1,001 reviews)
8.4/10
Very good
(1,001 reviews)
"Buena ubicación"
$123 nightly
The price is $139
$139 total
Nov 29 - Nov 30
Total with taxes and fees
Four Points by Sheraton San Jose Sabana
Four Points by Sheraton San Jose Sabana3.5 star property
5.8 mi from San Juan
8.8 out of 10, Excellent, (1,000 reviews)
8.8/10
Excellent
(1,000 reviews)
$114 nightly
The price is $129
$129 total
Nov 14 - Nov 15
Total with taxes and fees
Hilton Garden Inn San Jose La Sabana
Hilton Garden Inn San Jose La Sabana3.5 star property
7 mi from San Juan
9.0 out of 10, Wonderful, (872 reviews)
9.0/10
Wonderful
(872 reviews)
$116 nightly
The price is $132
$132 total
Dec 6 - Dec 7
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.
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 to find the best San Juan package deals?
Start your search for a San Juan package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Amenities," 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, 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 adventure underway.
When to book a vacation package to San Juan?
Secure fantastic discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for a spur-of-the-moment San Juan getaway.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.