San Juan Vacations from $1,327

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Your San Juan Vacation

When a fun city getaway is calling, answer it with a vacation package to San Juan. The neighborhood of Amón, which is great for cafes, nightlife and bars and pubs, makes an excellent base for your adventures. If sightseeing is on the to-do list during your trip to San Juan, swing by well-known attractions like National Museum of Costa Rica, National Theater and National Park. Check out Expedia's extensive range of travel options and start planning your ideal vacation to San Juan today.

The Latest San Juan Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 28 - Jan 2

    Way to Heaven Luxury Glamping + Flight

    Monteverde
    5 nights
    2.0 star property
    9.6/10 - 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, 2026
    Roundtrip • Miami (MIA) - San José (SJO)
    MIA - SJO • Nonstop SJO - MIA • 1 stop
    $2,238
    $1,327
    per traveler
    found 1 day ago
    Way to Heaven Luxury Glamping
  • Jan 4 - Jan 8

    Fondavela Hotel + Flight

    Monteverde
    4 nights
    4.5 star property
    8.6/10 - Excellent (416 reviews)
    Roundtrip • Boston (BOS) - San José (SJO)
    BOS - SJO • 1 stop SJO - BOS • 2 stops
    $11,685
    $1,455
    per traveler
    found 1 day ago
    Fondavela Hotel
  • Jan 23 - Jan 28

    The Springs Resort and Spa at Arenal + Flight

    Monterrey
    5 nights
    5.0 star property
    9.8/10 - Exceptional (1,005 reviews)
    "Wonderful staff throughout!"
    Reviewed November 7, 2026
    Roundtrip • Boston (BOS) - San José (SJO)
    BOS - SJO • 1 stop SJO - BOS • 1 stop
    $3,891
    $2,178
    per traveler
    found 1 day ago
    The Springs Resort and Spa at Arenal
  • Jan 23 - Jan 28

    Gaia Hotel And Reserve - Adults Only + Flight

    Manuel Antonio
    5 nights
    4.5 star property
    9.6/10 - Exceptional (544 reviews)
    "Excelente atención y el hotel es muy hermoso y bien ubicado"
    Reviewed October 19, 2026
    Roundtrip • Boston (BOS) - San José (SJO)
    BOS - SJO • 1 stop SJO - BOS • 1 stop
    $3,743
    $2,236
    per traveler
    found 1 day ago
    Gaia Hotel And Reserve - Adults Only
  • Dec 27 - Jan 1

    Finca Sunset Monteverde + Flight

    Monteverde
    5 nights
    2.0 star property
    9.8/10 - 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, 2026
    Roundtrip • Boston (BOS) - San José (SJO)
    BOS - LIR • Nonstop LIR - BOS • Nonstop
    Save 100% on your flight
    $9,473
    $5,879
    per traveler
    found 12 hours ago
    Finca Sunset Monteverde

Discover the most popular places to visit in San Juan

What to do in San Juan

San Juan Hotel Deals

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 is the best time to go to San Juan?

The best time to go for a San Juan vacation package is December and March, which are the peak months for demand. February is also a busy month for travelers. During these periods, you'll find the most activity and a vibrant atmosphere for your San Juan vacation.


For those seeking a quieter trip with potentially lower prices, consider traveling during August to October. These months typically see the lowest demand.

How can I save money on a San Juan vacation package?

When you bundle, you can save up to 30%*. To save money on a San Juan package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

What are the top things to do in San Juan?

San Juan, an outdoor and nature destination known for family-friendly attractions, offers a variety of activities for your San Juan vacation:


Browse and book things to do in San Juan on Expedia.

Do you need to rent a car in San Juan, or is public transport enough?

For a San Juan vacation package with flights, renting a car offers the most flexibility, especially since San Juan is an outdoor and nature destination with many attractions spread out. The area is well-served by a network of national routes, including National Route 5, 32, and 39, making it easy to explore at your own pace.


While local buses are available, and the Interurbano Line operated by Incofer provides rail transportation, a car allows you to easily reach various outdoor activities and scenic spots that define a San Juan vacation. This is particularly helpful for exploring areas outside the immediate city center.

Can I change or cancel my San Juan vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking San Juan vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later San Juan vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your San Juan vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to San Juan?

To find last-minute vacation packages to San Juan, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on San Juan vacation packages?

Free cancellation on a San Juan vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a San Juan vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your San Juan getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my San Juan vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.