San Mateo Vacations from $275

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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.
Marble Waters Hotel & Suites, Trademark by Wyndham

Marble Waters Hotel & Suites, Trademark by Wyndham

3 out of 5
East Arlington
Price was $365, price is now $275 per person
$275
per person
Mar 23 - Mar 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
6.4/10 (1,002 reviews)
Very nice hotel, clean room and hallways. Courteous service and great staff. Good location. Close to shopping and beach.

Reviewed on Dec 21, 2025

Amelia by the South

Amelia by the South

4 out of 5
Save 100% on your flight
Price was $6,510, price is now $4,314 per person
$4,314
per person
Apr 12 - Apr 17
found 10 hours ago
Roundtrip non-stop flight included
Islip (ISP) to Jacksonville (JAX)
No reviews
Amelia by the Sea

Amelia by the Sea

4 out of 5
Save 100% on your flight
Price was $6,537, price is now $4,341 per person
$4,341
per person
Apr 12 - Apr 17
found 10 hours ago
Roundtrip non-stop flight included
Islip (ISP) to Jacksonville (JAX)
No reviews
The Villas of Amelia Island

The Villas of Amelia Island

4 out of 5
Save 100% on your flight
Price was $739, price is now $549 per person
$549
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
8.4/10 Very Good! (1,115 reviews)
So while it is literally on the beach, the room is a little dated and doesn't get traditional turn down service, which would be nice. The space is small, but is doable. Value to price wasn't there for me. We'll probably stay in the main hotel next time.

Reviewed on Feb 2, 2026

Hyatt Regency Jacksonville

Hyatt Regency Jacksonville

4 out of 5
Downtown Jacksonville
Price was $575, price is now $429 per person
$429
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
9/10 Wonderful! (1,352 reviews)
Yes great room , really clean

Reviewed on Jan 31, 2026

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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
$62 nightly
The price is $69 total per night from Feb 4 to Feb 5
$69 total
Feb 4 - Feb 5
Total with taxes and fees
6.8/10 (142 reviews)
Nice staff

Reviewed on Jan 23, 2026

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
$85 nightly
The price is $95 total per night from Feb 4 to Feb 5
$95 total
Feb 4 - Feb 5
Total with taxes and fees
8/10 Very Good! (1,001 reviews)
Very Clean accommodations, Friendly Staff & Great Price⭐️

Reviewed on Jan 18, 2026

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
$109 nightly
The price is $122 total per night from Feb 8 to Feb 9
$122 total
Feb 8 - Feb 9
Total with taxes and fees
7.4/10 Good! (1,003 reviews)
Nice stay with clean room, friendly staff and great breakfast.

Reviewed on Jan 29, 2026

Holiday Inn Express & Suites Palm Coast I95 by IHG
See all 713 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 $275 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.