San Mateo Vacations from ￥142,486

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The Latest San Mateo Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Urbana Hotel

Urbana Hotel

2 out of 5
San Juan Antiguo
Price was ￥208,614, price is now ￥142,486 per person
￥142,486
per person
Jan 30 - Feb 3
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to San Juan (SJU)
8.6/10 Excellent! (368 reviews)
Great location, super clean. I woukd stay again

Reviewed on Nov 10, 2025

Ola Boutique Hotel

Ola Boutique Hotel

4.5 out of 5
Condado
Price was ￥261,462, price is now ￥164,150 per person
￥164,150
per person
Jan 30 - Feb 3
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to San Juan (SJU)
9.2/10 Wonderful! (542 reviews)
New mattress is a priority! The one we slept on was sinking in the middle. Very uncomfortable!!! Other than that it was a very good stay. The people who work there are very nice. Very clean.

Reviewed on Nov 10, 2025

OLV Fifty Five - Adults Only

OLV Fifty Five - Adults Only

4.5 out of 5
Condado
Save 100% on your flight
Price was ￥365,781, price is now ￥244,134 per person
￥244,134
per person
Jan 30 - Feb 3
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to San Juan (SJU)
8.6/10 Excellent! (563 reviews)
Amazing location , helpful attentive kind staff , unique vibes definitely would recommend

Reviewed on Oct 30, 2025

Aire de O:live

Aire de O:live

4 out of 5
Isla Verde
Save 100% on your flight
Price was ￥351,820, price is now ￥240,842 per person
￥240,842
per person
Jan 30 - Feb 3
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to San Juan (SJU)
9/10 Wonderful! (290 reviews)
Everything great. The only bad thing was the housekeeping knocking the door very early in the morning.

Reviewed on Nov 10, 2025

Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)

Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)

4 out of 5
Condado
Save 100% on your flight
Price was ￥373,952, price is now ￥260,879 per person
￥260,879
per person
Jan 30 - Feb 3
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to San Juan (SJU)
9/10 Wonderful! (643 reviews)
Beautiful hotel, amazing staff

Reviewed on Oct 30, 2025

Where to stay in San Mateo

Find the best San Mateo areas and neighborhoods for the activities you enjoy most. Learn more about San Mateo
San Juan

Old San Juan

4.5/5(354 area reviews)

The fascinating museums and captivating waterfront views are top of the list for many visitors to Old San Juan. A stop by Port of San Juan or Pier 4 might round out your trip.

Find hotels in Old San Juan

San Mateo Hotel Deals

The Looking Glass Hotel

The Looking Glass Hotel

2 out of 5
1661 Av. Juan Ponce de León, San Juan, Puerto Rico
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (246 reviews)
Booked this hotel for one night before a cruise. Very clean and perfect for my stay. There is no elevator, however, the staff will assist with taking the luggage up and down. I booked a room on the first floor, but was placed on the second floor. Very kind and professional staff. Definitely recommend ...

Reviewed on Nov 6, 2025

Get rates
The Looking Glass Hotel
The Royal Sonesta San Juan

The Royal Sonesta San Juan

4 out of 5
5961 Isla Verde Avenue, Carolina
Fully refundableReserve now, pay when you stay
The price is ￥50,686 per night from Nov 16 to Nov 17
￥50,686
￥67,402 total
Nov 16 - Nov 17
includes taxes & fees
9/10 Wonderful! (2,116 reviews)
Beautiful Resort. The staff was friendly and professional right down to the housekeeping staff. The rooms were clean and spacious with great amenities. We loved the coffee. The grounds and pool area were immaculate. Plenty of chairs at the pool and on the beach with towels provided. We loved the ...

Reviewed on Nov 10, 2025

The Royal Sonesta San Juan
Hyatt Vacation Club at Hacienda del Mar, Dorado

Hyatt Vacation Club at Hacienda del Mar, Dorado

3.5 out of 5
301 Hwy 693, Dorado, Vega Alta
Fully refundable
The price is ￥20,822 per night from Nov 30 to Dec 1
￥20,822
￥29,412 total
Nov 30 - Dec 1
includes taxes & fees
9.2/10 Wonderful! (2,791 reviews)
The maintenence on the property was impeccable! The staff was amazing. Highly recommend to any of my friends or family. The parking lot was about the only thing I'd say needs alittle upgrade (paving) other than that my wife and i are beyond satisfied with the service!

Reviewed on Nov 10, 2025

Hyatt Vacation Club at Hacienda del Mar, Dorado
See all 3,884 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.

Frequently asked questions

How much does a San Mateo vacation package cost?
Get set to book, because a getaway to San Mateo starts from an affordable ￥142,486. When you combine your hotels, flights and car rentals into a travel package, you'll score the best bargains.
How do I get a cheap travel package to San Mateo?
You'll save big if you combine your flights, hotels and car rentals into a San Mateo vacation package. Sometimes cheap packages mean fewer choices. But not with Expedia. We offer over 550 partner airlines and 1,000,000 hotels across the world, which means you'll always have plenty of options to choose from. Like to save even more? Add some fun activities to your package deal and unlock even bigger discounts! After all, travel is about more than just getting to your destination.
Where should I stay in San Mateo?
Most visitors to San Mateo include Luquillo Beach and Puerto Rico Convention Center on their itineraries. Why not book a hotel as close as possible to these main attractions?
How far in advance should I book my San Mateo vacation?
The earlier you book, the better. Air carriers generally advertise flights up to 12 months in advance, and this is a fantastic opportunity to land some of the lowest prices. Just been told you need to take all your vacation days next week? No need to worry. Expedia are never short on fantastic deals to whisk you away on the getaway of your dreams, at an affordable price.
What does an Expedia San Mateo travel package include?
Much of that depends on you. You can choose from a variety of San Mateo bundles, such as a hotel, rental car and flight. You can also book a hotel with a flight, or a rental car with a flight. Once you've made your booking, you can add on the fun stuff like activities and tours. Whatever your perfect San Mateo vacation looks like, you'll save!
What should I know before booking a San Mateo travel package?
When you book your hotels, flights and car rentals together, you'll be rewarded with great discounts. Whether you're organizing a beach escape in a villa or would rather stay in a ritzy city hotel, Expedia can help make it happen.
Can I choose my airline with a San Mateo Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines throughout the world. Our vacation packages give you the freedom to take your pick of available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my San Mateo vacation package?
Whether it's your flight or hotel, yes, you can amend or cancel it. Locked in your San Mateo vacation package in the last 24 hours? You may be able to make any changes for free. For bookings made more than 24 hours ago, you may incur a charge from your airline, hotel or car rental company. For more information, visit our Customer Service Portal. We're here to help you each step of the way.

Discover the most popular places to visit in San Mateo

Luquillo Beach featuring a beach

Luquillo Beach

Sample local street food or doze under a palm tree on this picturesque stretch of coast.

Luquillo Beach
Condado Beach featuring kayaking or canoeing, a sandy beach and tropical scenes

Condado Beach

This beach within the bustling city of San Juan is the perfect place to relax for a few hours.

Condado Beach
El Morro which includes general coastal views and heritage elements

Castillo San Felipe del Morro

This walled fortress was once used to protect Puerto Rico from invading colonies, and today offers visitors a dramatic reminder of that history.

Castillo San Felipe del Morro

Things to do

City Lights / GLOW

LED Kayak Night Glow Tour in Condado Lagoon

￥11,450
per adult
92% of travellers recommend
LED Kayak Night Glow Tour in Condado Lagoon
Single female snorkeler in the ocean off the coast of Puerto Rico

Catamaran Sail & Snorkeling in the Caribbean with Lunch

￥28,089
per traveler
90% of travellers recommend
Catamaran Sail & Snorkeling in the Caribbean with Lunch
Puerto Rico: UTV and Can-Am Sightseeing Tours

Puerto Rico: UTV and Can-Am Sightseeing Tours

￥10,379
per adult
76% of travellers recommend
Puerto Rico: UTV and Can-Am Sightseeing Tours
See all activities in San Juan
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.