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San Mateo Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top San Mateo vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Sept 24 - Sept 30

    Casa Lamia + Flight

    Manuel Antonio
    6 nights
    3.5 star property
    8.4/10 - Very good (111 reviews)
    "exelente hotel"
    Reviewed July 17, 2026
    Roundtrip • Toronto (YTO) - San José (SJO)
    YYZ - SJO • 1 stop SJO - YYZ • 2 stops
    CA $1,884
    CA $981
    per traveller
    found 7 hours ago
    Casa Lamia
  • View from property
    Aug 29 - Sept 4

    Cielo Lodge + Flight

    Golfito
    6 nights
    3.0 star property
    10/10 - Exceptional (6 reviews)
    "Our stay at Cielo Lodge was absolutely unforgettable and exceeded every expectation. From the moment we arrived, the staff made us feel genuinely welcome with their warmth, attentiveness, and willingness to help with anything we needed. Their hospitality truly made the experience extra special. The food was another highlight of our trip — every meal was incredibly fresh, flavorful, and beautifully prepared. The local ingredients and creative dishes gave us a true taste of Costa Rica, and dining..."
    Reviewed May 27, 2026
    Roundtrip • Toronto (YTO) - San José (SJO)
    YYZ - SJO • 1 stop SJO - YYZ • 2 stops
    CA $3,300
    CA $1,803
    per traveller
    found 1 day ago
    Cielo Lodge
  • Hallway
    Aug 30 - Sept 4

    Noah's Forest by Tifakara + Flight

    La Fortuna
    5 nights
    4.5 star property
    9.8/10 - Exceptional (413 reviews)
    "This is hands down the best hotel we have ever stayed at! Its absolutely beautiful. The staff is so friendly and helpful. Very clean. The pool was a lot of fun for our 6 year old daughter. The breakfast was incredible! We would stay here again in a heart beat. Shout out to the whole staff team at this hotel. You really know how to make sure guests are well taken care of and happy."
    Reviewed July 15, 2026
    Roundtrip • Toronto (YTO) - San José (SJO)
    YTZ - SJO • 1 stop SJO - YYZ • 2 stops
    CA $2,492
    CA $1,534
    per traveller
    found 1 day ago
    Noah's Forest by Tifakara
  • Poolside bar
    Sept 30 - Oct 4

    The Springs Resort and Spa at Arenal + Flight

    Monterrey
    4 nights
    5.0 star property
    9.8/10 - Exceptional (1,001 reviews)
    "El personal es excelente, un plus que tenga lavadora de ropa y secadora , los cuartos amplios , estacionamiento adecuado y de nuevo el personal hace el hotel , además de sus diferentes pisicinas térmicas. Los costos para desayuno, almuerzo , comida es un poco alto pero de muy buena calidad. Tomar en cuenta que todas las actividades son extras o pagadas a parte."
    Reviewed July 21, 2026
    Roundtrip • Toronto (YTO) - San José (SJO)
    YYZ - SJO • 1 stop SJO - YYZ • 2 stops
    CA $3,462
    CA $2,171
    per traveller
    found 13 hours ago
    The Springs Resort and Spa at Arenal
  • Outdoor pool, sun loungers
    Sept 9 - Sept 14

    Monte Carlo Luxury Condominiums + Flight

    Jacó
    5 nights
    3.5 star property
    9.4/10 - Exceptional (103 reviews)
    Roundtrip • Toronto (YYZ) - San José (SJO)
    YYZ - SJO • 1 stop SJO - YYZ • 2 stops
    CA $1,962
    CA $1,239
    per traveller
    found 22 hours ago
    Monte Carlo Luxury Condominiums

What to do in San Mateo

Monkey, Sloth and Jaco Beach Adventure

Monkey, Sloth and Jaco Beach Adventure

CA $128
per adult
0% of travellers recommend
Monkey, Sloth and Jaco Beach Adventure
See all activities in San Mateo

San Mateo Hotel Deals

Outdoor dining

Hotel Boutique Iguana Verde

Hotel Boutique Iguana Verde
3.5 star property
3.2 km from San Mateo
8.8 out of 10, Excellent, (150 reviews)
"We chose the hotel for it's convenient location in the city of Orotina , where we were visiting relatives . The staff was good , perhaps a little inattentive on check out. The reception office was closed and I had to look around for someone to return my key. Be advice there's is a very noisy soccer academy right next door . We were alocated on room 11 , close to the academy . It can be an issue if you are trying to rest early evening ."
The price is CA $184
CA $207 total
includes taxes & fees
Aug 19 - Aug 20
Hotel Boutique Iguana Verde
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.
See all properties in San Mateo

Frequently Asked Questions

How much does a San Mateo vacation package cost?

Offering great value package deals from CA $981 on Expedia, you'll be pleasantly surprised at how much a vacation to San Mateo costs! Our packages mean less travel planning for you and greater savings.

What are the cheapest months to go to San Mateo?

The off-season is the best time to travel to San Mateo if you're trying to keep costs down. Another tip for getting cheap San Mateo vacation packages? Avoid visiting during public holidays and any major events.

How many days is enough for San Mateo?

The ideal length for your San Mateo vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you enough time to go to all the major sights and discover some hidden gems along the way.

How to find the best San Mateo package deals?

Landing a cheap San Mateo package deal is a breeze with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and see what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most wallet-friendly San Mateo package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.

Is it cheaper to book a San Mateo vacation as a package?

An Expedia vacation package could land you great savings when compared to arranging accommodations and flights individually. Better still, you can tailor your San Mateo getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.

When to book a vacation package to San Mateo?

Secure fantastic discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment San Mateo escape.

How to plan a trip to San Mateo?

  1. Choose your travel dates: The things you plan to do in San Mateo and your preferred season will help you decide when to go.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and meals to activities and flights. Your hotel will likely be the largest expense during your trip to San Mateo.
  3. Decide how long to go away for: Now that you know more about San Mateo, you can figure out the right length of your vacation. Put together a rough itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to find a San Mateo vacation package that brings all your bookings together.

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