San Mateo Holidays from AU$1,797

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Your San Mateo Holiday

Book a San Mateo holiday package and discover the rhythm and vibe of this interesting neighbourhood. 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 holiday with Expedia and get to where you're going your way.

Top Holiday Package Deals in San Mateo

Price found within the past 48 hours. Click for updated prices.
The Tryst Beachfront Hotel

The Tryst Beachfront Hotel

3.5 out of 5
Condado
Price was AU$2,425, price is now AU$1,797 per person
AU$1,797
per person
12 Feb - 16 Feb
found 1 day ago
Return direct flight included
Washington (WAS) to San Juan (SJU)
8.2/10 Very Good! (581 reviews)
Good food and cocktails.

Reviewed on 4 Dec 2025

OLV Fifty Five - Adults Only

OLV Fifty Five - Adults Only

4.5 out of 5
Condado
Save 100% on your flight
Price was AU$3,850, price is now AU$2,188 per person
AU$2,188
per person
12 Feb - 16 Feb
found 1 day ago
Return direct flight included
Washington (WAS) to San Juan (SJU)
8.6/10 Excellent! (577 reviews)
The staff was amazing, best hotel stay I’ve had in awhile

Reviewed on 30 Nov 2025

Aire de O:live

Aire de O:live

4 out of 5
Isla Verde
Save 100% on your flight
Price was AU$3,706, price is now AU$2,347 per person
AU$2,347
per person
12 Feb - 16 Feb
found 1 day ago
Return direct flight included
Washington (WAS) to San Juan (SJU)
9/10 Wonderful! (328 reviews)
When it rained, the ceiling of Room 505 was leaking!

Reviewed on 1 Dec 2025

Ola Boutique Hotel

Ola Boutique Hotel

4.5 out of 5
Condado
Save 100% on your flight
Price was AU$3,093, price is now AU$1,992 per person
AU$1,992
per person
12 Feb - 16 Feb
found 1 day ago
Return direct flight included
Washington (WAS) to San Juan (SJU)
9.2/10 Wonderful! (589 reviews)
My family and I stood for one night and it was a great hotel. When we first walked in you can immediately smell how clean it is. The staff were super sweet ! We had breakfast there and it was small BUT PERFECT for my family. We had ham, eggs, toast, waffle sticks. Our room itself was big and there was 5 of us. Beautiful hotel. Loved it

Reviewed on 4 Dec 2025

Las Casitas Village at El Conquistador

Las Casitas Village at El Conquistador

4.5 out of 5
Cabezas
Save 100% on your flight
Price was AU$3,938, price is now AU$2,797 per person
AU$2,797
per person
12 Feb - 16 Feb
found 1 day ago
Return direct flight included
Washington (WAS) to San Juan (SJU)
9.2/10 Wonderful! (126 reviews)
Everything was great

Reviewed on 4 Dec 2025

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
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 Pier 4 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
9.2/10 Wonderful! (262 reviews)
Clean room and staff, plus some workout amenities and cold water in every floor

Reviewed on 28 Nov 2025

Get rates
The Looking Glass Hotel
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 AU$353 per night from 15 Dec to 16 Dec
AU$353
15 Dec - 16 Dec
includes taxes & fees
9.2/10 Wonderful! (2,919 reviews)
Excellent place!! We will definitely be back!

Reviewed on 3 Dec 2025

Hyatt Vacation Club at Hacienda del Mar, Dorado
The Condado Plaza Hotel

The Condado Plaza Hotel

4 out of 5
999 Ashford Avenue San Juan
Fully refundableReserve now, pay when you stay
The price is AU$324 per night from 14 Dec to 15 Dec
AU$324
14 Dec - 15 Dec
includes taxes & fees
7.8/10 Good! (1,856 reviews)
Every thing was fine

Reviewed on 2 Dec 2025

The Condado Plaza Hotel
See all 3,874 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.
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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 AU$1,797. 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

Port of San Juan

Port of San Juan

4.5/5(2 reviews)

Explore the waterfront in San Juan with a trip to Port of San Juan. Discover the area's top-notch restaurants and its acclaimed art galleries.

Port of San Juan
Luquillo Beach featuring a sandy beach

Luquillo Beach

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

Luquillo Beach
Condado Beach which includes kayaking or canoeing, tropical scenes and a beach

Condado Beach

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

Condado Beach

Activities

Puerto Rico: UTV and Can-Am Sightseeing Tours

Puerto Rico: UTV and Can-Am Sightseeing Tours

AU$105
per adult
76% of travellers recommend
Puerto Rico: UTV and Can-Am Sightseeing Tours
San Juan: Old San Juan Sunset Cruise with Drinks & Transfer

San Juan: Old San Juan Sunset Cruise with Drinks & Transfer

AU$153
per adult
90% of travellers recommend
San Juan: Old San Juan Sunset Cruise with Drinks & Transfer
Single female snorkeler in the ocean off the coast of Puerto Rico

Catamaran Sail & Snorkeling in the Caribbean with Lunch

AU$284
per traveller
90% of travellers recommend
Catamaran Sail & Snorkeling in the Caribbean with Lunch
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.