San Mateo Vacations from $519

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The Latest San Mateo vacation packages

Price found within the past 48 hours. Click for updated prices.
Arenal Roca Suites

Arenal Roca Suites

3 out of 5
Save 100% on your flight
Price was $1,028, price is now $519 per person
$519
per person
Jan 22 - Jan 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San José (SJO)
8.4/10 Very Good! (40 reviews)
This place was unbelievable. The view.....I have no words. Great condo. Good food. (Breakfast) not one bad thing I could say. Only be prepared for the seclusion. Nothing around so bring what you might want to eat and drink besides breakfast

Reviewed on Nov 27, 2025

Monte Carlo Luxury Condominiums

Monte Carlo Luxury Condominiums

3.5 out of 5
Price was $1,979, price is now $822 per person
$822
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San José (SJO)
9.4/10 Exceptional! (94 reviews)
Love the Monte Carlo. Would definitely stay again.

Reviewed on Aug 29, 2025

Vista Suites at Parador

Vista Suites at Parador

2.5 out of 5
Price was $2,774, price is now $1,188 per person
$1,188
per person
Jan 19 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San José (SJO)
10/10 Exceptional! (1 review)
Beautiful setting and comfortable room in the Vista Suites. Lots of picture taking on the property of wildlife. Very friendly staff and great personalized service.

Reviewed on Nov 9, 2025

Casitas Coloradas Puerto Viejo

Casitas Coloradas Puerto Viejo

2 out of 5
Price was $202,417, price is now $99,038 per person
$99,038
per person
Jan 14 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to San José (SJO)
No reviews
The Tranquilo Lodge

The Tranquilo Lodge

4 out of 5
Price was $2,854, price is now $1,438 per person
$1,438
per person
Feb 28 - Mar 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San José (SJO)
10/10 Exceptional! (33 reviews)
Our stay at Tranquilo Lodge was an absolute dream. Sebastien and Christophe are the most amazing hosts. Sebastien helped us plan out the best 4-5 day itenerary and was always around to help with anything we needed during our stay. The grounds are beautiful and maintained well and the view from the pool is absolutely stunning. The serving staff Cristina and Alex were so friendly and attentive. The Chef cooked up amazing lunches and lovely 3-4 course dinners. My wife and I look forward to coming back to Drake Bay to visit everyone at Tranquilo Lodge again in the future !

Reviewed on May 5, 2025

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San Mateo Hotel Deals

Buen Camino Hotel, San Mateo

Buen Camino Hotel, San Mateo

3 out of 5
Finca Ecologica del Bosque San Mateo Alajuela Province
9.2/10 Wonderful! (39 reviews)
Overall this was a great Property for my family. We are a family of 4, we had a cozy 2 bedroom unit, complete with sitting area and backyard. The second bedroom had 2 twin beda which was great for the boys not having to share a bed. Things to note...the hotel is up on a mountain, you need a sturdy ...

Reviewed on Jul 9, 2025

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Buen Camino Hotel, San Mateo
Fiesta Resort Central Pacific - All Inclusive

Fiesta Resort Central Pacific - All Inclusive

3.5 out of 5
El Roble 23 El Roble Puntarenas
Fully refundableReserve now, pay when you stay
$193 nightly
The price is $218 total per night from Dec 11 to Dec 12
$218 total
Dec 11 - Dec 12
Total with taxes and fees
7.6/10 Good! (1,128 reviews)
G

Reviewed on Dec 3, 2025

Fiesta Resort Central Pacific - All Inclusive
Hotel Punta Leona

Hotel Punta Leona

3 out of 5
Punta Leona Garabito Tárcoles Puntarenas
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $149 total per night from Dec 7 to Dec 8
$149 total
Dec 7 - Dec 8
Total with taxes and fees
8/10 Very Good! (962 reviews)
A beautiful place to relax and have a great vacation.

Reviewed on Dec 2, 2025

Hotel Punta Leona
See all 680 properties in San Mateo
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 Mateo Vacation Packages

San Mateo Essential Information

Language
Spanish
Currency
Costa Rican colóns
Local Welcome
¡Hola!
Local Goodbye
Adiós
Closest Airport
Juan Santamaria Intl. Airport (SJO)
Max Temp Winter
80ºF
Max Temp Summer
80ºF

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Frequently asked questions

How much does a San Mateo vacation package cost?
You'll find cheap prices from $519 on Expedia for your San Mateo escape. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to San Mateo costs.
What are the cheapest months to go to San Mateo?
August, September and December are the best times to look for cheap San Mateo vacation packages. Traveling in less busy periods means you can typically find lower prices on flights and accommodations.
How many days is enough for San Mateo?
With a well-organized itinerary, you can easily hit the top San Mateo sights in a few days. But if you want to discover lesser-known spots or take day trips, consider booking your San Mateo vacation for longer.
How to find the best San Mateo package deals?
Use Expedia's filter tool to help you find some tempting San Mateo package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for San Mateo package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a San Mateo vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component individually. And you'll still get the flexibility to create a customized San Mateo vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to San Mateo?
Secure incredible discounts by reserving your flights early with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment San Mateo trip.
How to plan a trip to San Mateo?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to San Mateo.
  2. Calculate your budget: Ensure you have enough money to cover everything from dining out and transportation to flights and experiences. Your hotel will likely be the biggest expense during your trip to San Mateo.
  3. Organize your San Mateo escape with Expedia's trip planning tool: Look for and book hotels and experiences all in one place. You can also collaborate with friends and family to plan an unforgettable trip to San Mateo together.
  4. Decide how long to go away for: Now that you're up to speed on San Mateo, you can figure out the perfect length of your vacation. Create a draft itinerary and allocate enough time to cover everything you want to see.
  5. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a tailored San Mateo vacation package.
  6. Book experiences or activities in advance: Whether it's entrance to a big attraction or a day trip in nature, you won't have to worry about missing out on the highlights of San Mateo. Find all the incredible things to do in San Mateo with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later San Mateo vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your San Mateo trip over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.