San Mateo Vacation Packages 2026 from $499

San Mateo flight + hotel vacation packages

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

Delta Hotels by Marriott™ Jacksonville Deerwood

Southside

Save 100% on your flight

$499

per person

May 30 - Jun 6

found 9 hours ago

Roundtrip flight included

Boston (BOS) to Jacksonville (JAX)

This hotel features an outdoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. A free area shuttle is offered as well.

Hammock Beach Golf Resort & Spa

Save 100% on your flight

$724

per person

Jun 23 - Jun 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Jacksonville (JAX)

This luxury resort features a private beach, a golf course, and free water park access. Bring the family and enjoy the lazy river, children's club, and mini golf. Enjoy a meal in one of the 9 restaurants and free perks like free self parking and WiFi in public areas.

The Ritz-Carlton, Amelia Island

Amelia City

Save 100% on your flight

$1,893

per person

Jul 9 - Jul 13

found 14 hours ago

Roundtrip flight included

Boston (BOS) to Jacksonville (JAX)

A golf course, a full-service spa, and 3 hot tubs are all featured at this luxury resort. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. There's fun for all ages with a children's club and an arcade/game room, and families will appreciate the onsite laundry facilities.

The Villas of Amelia Island

Save 100% on your flight

$813

per person

Jul 9 - Jul 13

found 14 hours ago

Roundtrip flight included

Boston (BOS) to Jacksonville (JAX)

This smoke-free vacation home features a golf course, a full-service spa, and 9 restaurants. Enjoy a day at the beach kayaking, or relax with beach cabanas. There's fun for all ages with a children's club and mini golf, and babysitting is an added bonus.

Margaritaville Jacksonville Beach

Save 100% on your flight

$581

per person

Jul 9 - Jul 13

found 14 hours ago

Roundtrip flight included

Boston (BOS) to Jacksonville (JAX)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.

Top San Mateo hotels deals

Quality Inn & Suites Palatka Riverfront

201 N 1st Street Palatka FL

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$103 total

May 5 - May 6

Total with taxes and fees

A marina and an outdoor pool are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.

Pool

Breakfast included

Red Roof Inn PLUS+ Palm Coast

10 Kingswood Dr Palm Coast FL

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$84 total

Apr 20 - Apr 21

Total with taxes and fees

This hotel features an outdoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking and a safe deposit box are also offered on site.

Old Town Inn - St Augustine South

2625 State Rd 207 Elkton FL

Free Cancellation

Reserve now, pay when you stay

$62 nightly

$69 total

Apr 19 - Apr 20

Total with taxes and fees

This motel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.

Microtel Inn & Suites by Wyndham Palm Coast I-95

16 Kingswood Dr Palm Coast FL

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$89 total

Apr 19 - Apr 20

Total with taxes and fees

A restaurant and an outdoor pool are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.

Pool

Breakfast included

Holiday Inn Express & Suites Palm Coast I95 by IHG

120 Garden St N Palm Coast FL

Free Cancellation

$105 nightly

$117 total

Apr 19 - Apr 20

Total with taxes and fees

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

Fairfield Inn & Suites Palm Coast I-95

400 Old Kings Rd Palm Coast FL

Free Cancellation

Reserve now, pay when you stay

$114 nightly

$128 total

Apr 19 - Apr 20

Total with taxes and fees

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

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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 are vacation packages to San Mateo?

Enjoy a memorable experience in San Mateo with a vacation package starting at just $499. Locking in tours, flights and hotels with Travelocity is so easy. On top of that, our vacation deals will leave you with more money in your pocket for loads of fun activities.

Where can I get the best vacation package deals for San Mateo?

You'll find amazing San Mateo package deals with Travelocity. Select from as many as 400 airlines and 1,000,000 properties worldwide and turn those vacation daydreams into a reality.

Why should I book my San Mateo vacation bundle via Travelocity?

Because life is one big journey, and we offer everything you could hope for to get you on your way. With our high-quality service and Price Match Guarantee, you can organize your trip with confidence. And you can rest easy while you're away knowing we've got your back with our round-the-clock support.

Will I save money on my San Mateo car rental if I book it with hotels and flights?

With a San Mateo vacation package, you can bundle your hotel, flight and car bookings and save a ton. When you're ready to discover the best of this exciting city, why not head to Universal Studios Florida? This famous attraction is 80 mi from San Mateo. With your own wheels, you'll be there in a jiffy.

What is the best time of year to go to San Mateo?

You'll pick up the best hotel prices around and pay the most during . You can usually expect it to be more relaxed in January, June and July, while you'll find more fellow travelers to meet in the months of August, September and December. It all comes down to how much you're willing to spend, the climate and how you deal with crowds.

Which airport is best for San Mateo?

Jacksonville Intl. Airport (JAX) is one of the busiest airports in San Mateo. It's roughly 60 mi north of the bustling downtown area. Other choices include Gainesville Regional Airport (GNV) (40 mi away from central San Mateo) and Orlando Sanford Intl. Airport (SFB) (60 mi away from central San Mateo).

Where should I stay when visiting San Mateo?

If you're searching for somewhere to spend your nights, have a look at the Looking For A Secluded, Peaceful Environment. It's the top pick for many travelers.