San Mateo Vacations from $356

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Your San Mateo Vacation

Our vacation packages to San Mateo let you customize your own adventure. Tailor your journey to suit your needs and interests and make the most of your time in this interesting city. A trip to San Mateo is a terrific opportunity to sightsee. Be sure to stop by big-name attractions such as Ravine Gardens State Park, Dunns Creek State Park and Palatka Municipal Golf Course. Whoever you're escaping with and whatever you plan to spend, your dream San Mateo vacation is only clicks away with Expedia.

The Latest San Mateo vacation packages

Price found within the past 48 hours. Click for updated prices.
Margaritaville Jacksonville Beach

Margaritaville Jacksonville Beach

2.5 out of 5
Price was $503, price is now $356 per person
$356
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Jacksonville (JAX)
9/10 Wonderful! (3,345 reviews)
Everything was great, beautiful property!!!

Reviewed on Dec 13, 2025

Amelia by the South

Amelia by the South

4 out of 5
Save 100% on your flight
Price was $5,413, price is now $3,358 per person
$3,358
per person
Feb 15 - Feb 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Jacksonville (JAX)
No reviews
Amelia by the Sea

Amelia by the Sea

4 out of 5
Save 100% on your flight
Price was $5,440, price is now $3,385 per person
$3,385
per person
Feb 15 - Feb 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Jacksonville (JAX)
No reviews
Omni Amelia Island Resort & Spa

Omni Amelia Island Resort & Spa

4 out of 5
Save 100% on your flight
Price was $783, price is now $560 per person
$560
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Jacksonville (JAX)
8.8/10 Excellent! (1,003 reviews)
The room was beautifully cleaned all the amenities you could want were there. The people were incredibly helpful at the hotel and super friendly!

Reviewed on Nov 21, 2025

Hilton Jacksonville At Mayo Clinic

Hilton Jacksonville At Mayo Clinic

4.5 out of 5
Save 100% on your flight
Price was $796, price is now $570 per person
$570
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Jacksonville (JAX)
9.4/10 Exceptional! (22 reviews)
Very clean nice rooms! Beds are terrible. It’s like someone slept on one side of the bedroom for 20 years without turning the bed….it goes uphill from one side to the other! Very nice room though with great facilities!

Reviewed on Dec 12, 2025

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San Mateo Hotel Deals

Old Town Inn - St Augustine South

Old Town Inn - St Augustine South

2625 State Rd 207 Elkton FL
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $84 total per night from Dec 14 to Dec 15
$84 total
Dec 14 - Dec 15
Total with taxes and fees
6.4/10 (71 reviews)
yes

Reviewed on Dec 7, 2025

Old Town Inn - St Augustine South
Red Roof Inn PLUS+ Palm Coast

Red Roof Inn PLUS+ Palm Coast

2.5 out of 5
10 Kingswood Dr Palm Coast FL
Fully refundableReserve now, pay when you stay
$63 nightly
The price is $71 total per night from Dec 17 to Dec 18
$71 total
Dec 17 - Dec 18
Total with taxes and fees
8/10 Very Good! (1,006 reviews)
Nice area to stay.

Reviewed on Dec 8, 2025

Red Roof Inn PLUS+ Palm Coast
Holiday Inn Express & Suites Palm Coast I95 by IHG

Holiday Inn Express & Suites Palm Coast I95 by IHG

3 out of 5
120 Garden St N Palm Coast FL
Fully refundable
$74 nightly
The price is $83 total per night from Jan 5 to Jan 6
$83 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
7.4/10 Good! (1,004 reviews)
The A/C needs to be taken care off and elevator only one was working

Reviewed on Dec 8, 2025

Holiday Inn Express & Suites Palm Coast I95 by IHG
See all 669 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.

Find the Best San Mateo Vacation Packages

San Mateo Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
70ºF
Max Temp Summer
90ºF
Top Sights
Ravine Gardens State Park, Dunns Creek State Park and Rice Creek Conservation Area

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Frequently asked questions

How much does a San Mateo vacation package cost?
Offering great value package deals from $356 on Expedia, you'll be pleasantly surprised at how much a vacation to San Mateo costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to San Mateo?
You can typically find reduced prices and greater availability in January, June and July. Explore our cheap San Mateo vacation packages and you could get some great off-season discounts.
How many days is enough for San Mateo?
Typically, a handful of days is enough to see the major sights during your San Mateo vacation. But if you'd like to have more time to rest or take day tours, think about extending your itinerary.
How to find the best San Mateo package deals?
Begin your search for a San Mateo package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect San Mateo package deal right away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your San Mateo adventure off to a flying start.
Is it cheaper to book a San Mateo vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking accommodations and flights separately. Better still, you can personalize your San Mateo escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to San Mateo?
If you're planning a spontaneous San Mateo getaway, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find amazing deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later San Mateo vacation packages?
If you're anything like us, you love discovering new places but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your San Mateo trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.