San Mateo Holidays

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Our guide on 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

Old San Juan

4/5(1 area review)

The interesting museums and 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.

Find hotels in Old San Juan

Our pick of the best 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
The price is NZ$212 per night from 17 May to 18 May
NZ$212
17 May - 18 May
includes taxes & fees
9.2/10 Wonderful! (389 reviews)
The staff at check in were helpful. The room was basic. Very small. Bed was MUCH more firm than we are used to. So, we didn’t have a very restful night. Bathroom is very small with the sink in the shower. Makes it difficult for someone to use the sink while another person is showering. Lack of an ...

Reviewed on 19 Apr 2026

The Looking Glass Hotel
Caribe Hilton

Caribe Hilton

4.5 out of 5
1 San Geronimo Street San Juan
Fully refundableReserve now, pay when you stay
The price is NZ$516 per night from 4 May to 5 May
NZ$516
4 May - 5 May
includes taxes & fees
8.6/10 Excellent! (2,654 reviews)
The pool was nice, although I swam in the ocean rather than the pool.

Reviewed on 19 Apr 2026

Caribe Hilton
Hyatt Vacation Club at Hacienda del Mar, Dorado

Hyatt Vacation Club at Hacienda del Mar, Dorado

3.5 out of 5
301 Hwy 693 Vega Alta
Fully refundable
The price is NZ$584 per night from 6 May to 7 May
NZ$584
6 May - 7 May
includes taxes & fees
9.4/10 Exceptional! (3,426 reviews)
Great place for a beach vacation. You have your own kitchen, dishwasher, washing machine, and get plenty of towels. Chairs and umbrellas are available at the beach. Wonderful staff and wonderful facility. Would recommend to rent a car.

Reviewed on 19 Apr 2026

Hyatt Vacation Club at Hacienda del Mar, Dorado
See all 3,876 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 holiday package cost?
Get set to book, because a getaway to San Mateo starts from an affordable . 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 holiday 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 Centre 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 holiday?
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 holiday 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 holiday 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 organising 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 holiday package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines throughout the world. Our holiday 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 holiday package?
Whether it's your flight or hotel, yes, you can amend or cancel it. Locked in your San Mateo holiday 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

Luquillo Beach

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

Luquillo Beach
Castillo San Felipe del Morro

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

Casino del Mar at La Concha Resort

Why not try your luck with a visit to Casino del Mar at La Concha Resort where you can enjoy the games and entertainment of this top casino in San Juan? Stroll along the seaside in this vibrant area or visit its top-notch restaurants.

Casino del Mar at La Concha Resort

Activities

El Yunque Rainforest Guided Hiking with Waterfall Tour

El Yunque Rainforest Guided Hiking Tour

NZ$150
per traveller
96% of travellers recommend
El Yunque Rainforest Guided Hiking Tour
El Yunque Waterslide and Waterfall Tour with Food and Photos

El Yunque Waterslide and Waterfall beach Tour with Food n Photos

NZ$118
per adult
96% of travellers recommend
El Yunque Waterslide and Waterfall beach Tour with Food n Photos
San Juan: Casa Bacardi Distillery Tour

San Juan: Casa Bacardi Distillery Tour

NZ$152
per adult
92% of travellers recommend
San Juan: Casa Bacardi Distillery Tour
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.