Holiday Homes in San Mateo

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Holiday Homes in San Mateo

Standard Queen Room w/Ensuite Bathroom
Relax in a stylish room with a large bed, striped wall design, and a unique lamp.

Standard Queen Room w/Ensuite Bathroom

9.0 out of 10, Wonderful, (36)
"property was exactly what was expected, will recommend and stay again. "
The price is AU$217
includes taxes & fees
4 Aug - 5 Aug
Standard Queen Room w/Ensuite Bathroom
Contemporary 3bedrooms 2bathrooms in private top floor locates@safe neighborhood
Guests can relax in a tranquil beach setting with a tent and plenty of space to unwind.

Contemporary 3bedrooms 2bathrooms in private top floor locates@safe neighborhood

10.0 out of 10, Exceptional, (61)
"We enjoyed our stay! The owner is delightful. "
The price is AU$781
includes taxes & fees
3 Sept - 4 Sept
Contemporary 3bedrooms 2bathrooms in private top floor locates@safe neighborhood
Deluxe Queen Room with View and Ensuite Bath
Step into a classic lobby with a grand staircase and arched window, surrounded by elegant decor.

Deluxe Queen Room with View and Ensuite Bath

9.8 out of 10, Exceptional, (6)
"We love that the room was clean and surprisingly there was not a lot of noise so we were able to sleep deep. They gave us a key to enter the building which was helpful. It was convenient for us because we were able to walk to get breakfast at different places. There is no parking available but overall we love staying here. I love that there was free coffee."
The price is AU$205
includes taxes & fees
4 Aug - 5 Aug
Deluxe Queen Room with View and Ensuite Bath
Vintage San Francisco Bay Area Home
Relax in a serene patio setting with a glass table and comfortable seating for four.

Vintage San Francisco Bay Area Home

9.0 out of 10, Wonderful, (76)
"We had a great time Cleanliness wasn't perfect but managed Kitchen need some upgrade "
Vintage San Francisco Bay Area Home
Absolutely Private President's Suite, Computer, Wi-Fi, Laundry, Pub. Parking
Surrounded by lush greenery, this serene setting features a stone well, a small pond, and a stone structure.

Absolutely Private President's Suite, Computer, Wi-Fi, Laundry, Pub. Parking

9.0 out of 10, Wonderful, (393)
"Clean and comforable. Ideal for our visit to city."
Absolutely Private President's Suite, Computer, Wi-Fi, Laundry, Pub. Parking
Clean & Lovely house close to everywhere
Spanning the Golden Gate strait, the iconic bridge offers stunning views of the surrounding landscape.

Clean & Lovely house close to everywhere

9.4 out of 10, Exceptional, (46)
"Place was inviting clean everything you would want and need would definitely stay again"
Clean & Lovely house close to everywhere
Relaxing & Peaceful 6BR Home w/HotTub/Game/Funtime
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and ample cabinetry.

Relaxing & Peaceful 6BR Home w/HotTub/Game/Funtime

9.4 out of 10, Exceptional, (13)
"We rented this house for a weekend get away and this place did not disappoint. Very clean and host is very responsive. Very close to the beach and stores. The house is very spacious and enjoyed the hot tub. Would definitely rent this place again."
The price is AU$1,112
includes taxes & fees
4 Aug - 5 Aug
Relaxing & Peaceful 6BR Home w/HotTub/Game/Funtime
Large Palo Alto Home, Pool, 5 beds/3 baths, in the Heart of Palo Alto
Enjoy a refreshing swim in the pool surrounded by lush greenery and a wooden fence.

Large Palo Alto Home, Pool, 5 beds/3 baths, in the Heart of Palo Alto

9.8 out of 10, Exceptional, (24)
"Great stay with lots of space for large groups. Small backyard/deck to hang out at and across the street from a park and cafe. Lots of space to sleep throughout the house. Check in was easy and hosts were communicative and easy to reach"
Large Palo Alto Home, Pool, 5 beds/3 baths, in the Heart of Palo Alto
LuxoStays | Westborough Beauty | 4BR Home in SSF
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and dishwasher, plus a microwave and coffee maker.

LuxoStays | Westborough Beauty | 4BR Home in SSF

9.6 out of 10, Exceptional, (8)
"Clean and warm home. Great views. Children friendly. "
LuxoStays | Westborough Beauty | 4BR Home in SSF
Stunning Oceanview Coastal Home – Beach, Trails, Family Activities
Experience the rugged beauty of the coastline with a natural archway and ocean views.

Stunning Oceanview Coastal Home – Beach, Trails, Family Activities

9.2 out of 10, Wonderful, (76)
"My daughter and I stayed here over spring break. This place was a great value. It served as a nice home base at the end of each day of sightseeing up and down the coast. It's an older building, with mostly updated finishings. The kitchen has all the basics, older but mostly functional (sharp knives not withstanding)."
The price is AU$549
includes taxes & fees
14 Aug - 15 Aug
Stunning Oceanview Coastal Home – Beach, Trails, Family Activities
Charming Garden Cottage- steps to historic Old Town Half Moon Bay
Enjoy cooking in this well-equipped kitchen with a central island, oven, and stainless steel refrigerator.

Charming Garden Cottage- steps to historic Old Town Half Moon Bay

9.8 out of 10, Exceptional, (49)
"Cute little place Clean and comfortable Great location Walking distance to downtown "
Charming Garden Cottage- steps to historic Old Town Half Moon Bay
West oakland home minutes from San Francisco FLEXIBLE CANCELLATION !
Relax on the outdoor patio with a wooden deck, surrounded by lush potted plants and comfortable seating.

West oakland home minutes from San Francisco FLEXIBLE CANCELLATION !

9.6 out of 10, Exceptional, (84)
"I came into town for work and combined it with a fun weekend with my kids. Our host couldn’t have been more wonderful. Location and amenities were great and hope to return again soon. "
West oakland home minutes from San Francisco FLEXIBLE CANCELLATION !
Cabo San Pedro - S.F. Ocean Views - Penthouse
Relax in this inviting space with a comfortable sofa, round table, and chairs, surrounded by a bookshelf and large windows offering a view of the sea.

Cabo San Pedro - S.F. Ocean Views - Penthouse

9.4 out of 10, Exceptional, (64)
"The views from this property are incredible, and it is up high enough that it feels peaceful to look down over the beach and the water! The bed is also very comfortable! Cool and unique property. "
Cabo San Pedro - S.F. Ocean Views - Penthouse
Bright & Peace 3BR, RWC Fresh Remodeled & Spotless
Enjoy cooking in this well-equipped kitchen with a refrigerator, stove, oven, and dishwasher.

Bright & Peace 3BR, RWC Fresh Remodeled & Spotless

10.0 out of 10, Exceptional, (1)
The price is AU$725
includes taxes & fees
14 Aug - 15 Aug
Bright & Peace 3BR, RWC Fresh Remodeled & Spotless
Test Property - E2E Vrbo
Living area

Test Property - E2E Vrbo

The price is AU$128
includes taxes & fees
4 Aug - 5 Aug
Test Property - E2E Vrbo
Entire 3 Bedroom 2 Bath house for 6 people Near SFO/SF/Bay Area Convenient Sweet
Enjoy cooking in this well-lit kitchen with an oven, microwave, and dishwasher.

Entire 3 Bedroom 2 Bath house for 6 people Near SFO/SF/Bay Area Convenient Sweet

9.8 out of 10, Exceptional, (65)
"Was a great place to stay, we had a group of 3 couples, was nice that each of us had a room to use with adequate space and the distance being just a 20min drive from events we were attending in SF made this a prime location for us. Also was nice to have stores just a few minutes away. Property was nice, easy to access and clean "
The price is AU$575
includes taxes & fees
13 Aug - 14 Aug
Entire 3 Bedroom 2 Bath house for 6 people Near SFO/SF/Bay Area Convenient Sweet
Entire Oceanview Coastal Retreat in Pacifica
Spanning the water, the iconic Golden Gate Bridge offers breathtaking views of the surrounding landscape.

Entire Oceanview Coastal Retreat in Pacifica

9.8 out of 10, Exceptional, (8)
"The house was beautiful and the view was perfect. Super close to restaurants and the beach."
The price is AU$757
includes taxes & fees
4 Aug - 5 Aug
Entire Oceanview Coastal Retreat in Pacifica
Economy Double Room with Ensuite Bathroom
Stunning lobby with a grand staircase and arched window, surrounded by elegant decor and lush greenery.

Economy Double Room with Ensuite Bathroom

8.6 out of 10, Excellent, (7)
"I liked this place, I’d stay again if I need to."
The price is AU$190
includes taxes & fees
4 Aug - 5 Aug
Economy Double Room with Ensuite Bathroom
Beach Villa Home - Walk to Beaches, Trails, Restaurants, Activities & more
Enjoy the ocean view from this room's balcony, featuring a deck and glass door leading to a cozy space with a shelving unit.

Beach Villa Home - Walk to Beaches, Trails, Restaurants, Activities & more

9.4 out of 10, Exceptional, (30)
"My wife had a great time."
The price is AU$897
includes taxes & fees
7 Aug - 8 Aug
Beach Villa Home - Walk to Beaches, Trails, Restaurants, Activities & more
San Francisco Retreat Just Steps from Golden Gate Park and Ocean Beach! by RedAwning
Fridge, microwave, oven, dishwasher

San Francisco Retreat Just Steps from Golden Gate Park and Ocean Beach! by RedAwning

9.8 out of 10, Exceptional, (30)
"Location near park was nice. The beds were very comfortable. Very easy communication with hosts. "
San Francisco Retreat Just Steps from Golden Gate Park and Ocean Beach! by RedAwning
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free