San Mateo Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Holiday Package Deals in San Mateo
Price found within the past 48 hours. Click for updated prices.
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
Isla Verde
1 out of top 10 points of interest in this area
White-sands, beautifully clear water and excellent water sports make this beach one of the most popular in Puerto Rico.
Condado
1 out of top 10 points of interest in this area
Oceanfront and upscale, Condado boasts picturesque beaches alongside hotels, nightclubs, casinos, and shops. Stroll through La Ventana al Mar park, and enjoy easy access to public transport via T21 and D53 bus routes.
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.
Santurce
2 out of top 10 points of interest in this area
Bask in the sun on Atlantic Ocean beaches and experience vibrant nightlife at La Placita de Santurce, while exploring museums like the Museum of Art of Puerto Rico. Enjoy easy access to public transportation via bus lines and the Tren Urbano.
Ocean Park
Upscale beachfront community with trendy beachgoers, Ocean Park offers kitesurfing and windsurfing opportunities. Stroll along Calle Loíza for bars, restaurants, and boutiques or unwind at nearby Parque Barbosa.
San Mateo Hotel Deals
The Looking Glass Hotel
1661 Av. Juan Ponce de León San Juan Puerto Rico
Fully refundable
CA $132
CA $144 total
Aug 30 - Aug 31
includes taxes & fees
9.2/10 Wonderful! (523 reviews)
"Bonnie was extremely understanding and accommodating. I really appreciated how attentive and kind she was, especially considering how late it was at night. The room was clean and comfortable. My only complaint was that I didn’t have water when I first arrived, but Bonnie made sure the issue was resolved ..."
Reviewed on Aug 22, 2026
Hyatt Regency Grand Reserve Puerto Rico
200 Coco Beach Blvd. Highway 955-I Río Grande
Fully refundableReserve now, pay when you stay
CA $362
CA $465 total
Sep 10 - Sep 11
includes taxes & fees
Fairmont El San Juan Hotel
6063 Isla Verde Avenue Carolina
Fully refundableReserve now, pay when you stay
CA $480
CA $686 total
Aug 28 - Aug 29
includes taxes & 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.
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 CA $1,119. 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.
Things to do
El Yunque Rainforest Guided Hiking Tour
CA $124
per traveller
96% of travellers recommend
San Juan: Casa Bacardi Distillery Tour
CA $63
per adult
94% of travellers recommend
Bioluminescent Bay Night Kayak Experience in Fajardo (transport optional)
CA $97
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.