San Mateo Vacations from $664
Book a Hotel + Flight or Car together to unlock savings
Your San Mateo Vacation
Book a San Mateo vacation package and discover the rhythm and vibe of this interesting neighborhood. With all your travel plans taken care of, the only thing you need to concentrate on here is living your best life. Wondering what to see and do during your trip to San Mateo? Nearby attractions like Jose Miguel Agrelot Coliseum, Hiram Bithorn Stadium and Condado Beach are great places to start. Don't just think about it — turn it into reality! Secure your ultimate San Mateo vacation with Expedia and get to where you're going your way.
The Latest San Mateo Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Isla Verde Beachfront Retreat With Parking
Isla Verde
Price was $1,579, price is now $664 per person
$664
per person
Jan 9 - Jan 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
10/10 Exceptional! (7 reviews)
Super nice place to stay at Isla Verde. Owner was super friendly and the place is clean,, a lot of space with included kitchen and wash/drying machine. Would consider again for sure.
Reviewed on Oct 5, 2026
Hotel Puerto Valdes
Puerta de Tierra
Price was $1,808, price is now $1,077 per person
$1,077
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
8.8/10 Excellent! (755 reviews)
Staff was excellent and very helpful during our stay especially Hector. Unfortunately the shuttle has been out of service and the hot tub needed cleaning. There were several other issues we encountered that were rectified by the Hector as well as other staff members at the time of need.
Reviewed on Nov 7, 2026
63 Bay View by Otium
Palmas
Price was $2,525, price is now $1,594 per person
$1,594
per person
Jan 13 - Jan 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
5/10 (4 reviews)
The sealant under the shower door was coming off, causing water to leak out. pull out couch was broken and due to it being broken I did not lift it to look for the remote that was stuck underneath. Came back one day and the door was wide open. Horrible communication. Uber and door dash could never find us. Not happy with my stay at ALL
Reviewed on Jun 15, 2026
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
Old San Juan
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 Castillo de San Cristobal might round out your trip.
San Mateo Hotel Deals
The Looking Glass Hotel
1661 Av. Juan Ponce de León San Juan Puerto Rico
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $135 total per night from Nov 10 to Nov 11
$135 total
Nov 10 - Nov 11
Total with taxes and fees
Hyatt Vacation Club at Hacienda del Mar, Dorado
301 Hwy 693 Vega Alta
Fully refundable
$179 nightly
The price is $195 total per night from Nov 30 to Dec 1
$195 total
Nov 30 - Dec 1
Total with taxes and fees
9.4/10 Exceptional! (4,209 reviews)
"6 of us did a long weekend trip, property was beautiful the staff was friendly and helpful. We stayed in a villa with full kitchen and walk out back door which was awesome for going right to the pool and beach. It was never too crowded by the pool, beach or bar. The restaurant there was properly ..."
Reviewed on Nov 9, 2026
AC Hotel by Marriott San Juan Condado
1369 Ashford Avenue San Juan
Fully refundableReserve now, pay when you stay
$256 nightly
The price is $279 total per night from Nov 25 to Nov 26
$279 total
Nov 25 - Nov 26
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.
Things to do
El Yunque Rainforest Guided Hiking Tour
$88
per traveler
96% of travellers recommend
Puerto Rico: The Beast Zipline at Toro Verde Adventure Park
$67
per adult
92% of travellers recommend
Puerto Rico: Toro Verde Adventure Park Zipline Bike Ticket
$56
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.