Guesthouse holiday rentals in San Mateo
Find and book unique guesthouse rentals on Airbnb
Top-rated Guesthouses in San Mateo
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for San Mateo guesthouses
Family-Friendly guesthouses
Guesthouse in Redwood City
4.88 out of 5 average rating, 538 reviewsCharming cottage, walk to Caltrain
4–11 Apr
Guesthouse in San Francisco
4.94 out of 5 average rating, 949 reviewsImmaculate studio space with free parking
3–10 Dec
Guesthouse in San Francisco
4.98 out of 5 average rating, 160 reviewsCozy 1 Bedroom (Twin) Private Bath and Entrance!
10–17 Jul
Guesthouse in Kensington
4.94 out of 5 average rating, 605 reviewsSecluded luxury cottage & hot tub
23–30 Mar
Guesthouse in Menlo Park
4.9 out of 5 average rating, 352 reviewsCottage near downtown Palo Alto
2–9 Oct
Guesthouse in Redwood City
4.97 out of 5 average rating, 177 reviewsMt Carmel Cottage Charmer-Bright, Stylish & Clean
17–24 Oct
Guesthouse in Redwood City
4.94 out of 5 average rating, 114 reviewsElegant & Convenient RWC Studio
2–9 Mar
Guesthouse in Mountain View
4.96 out of 5 average rating, 261 reviewsPrivate studio in downtown
8–15 Jul
Guesthouses with a patio
Guesthouse in Menlo Park
4.95 out of 5 average rating, 158 reviewsCharming, modern, restorative, private studio
7–14 Sep
Guesthouse in Woodside
4.97 out of 5 average rating, 152 reviewsSkyHigh Redwoods Retreat with Bay Views
8–15 Oct
Guesthouse in Boulder Creek
4.96 out of 5 average rating, 113 reviewsCustom Tiny Home Retreat in the Redwoods
14–21 Jul
Guesthouse in Boulder Creek
4.99 out of 5 average rating, 149 reviewsDigital Nomad Retreat
14–21 Oct
Guesthouse in San Jose
4.98 out of 5 average rating, 106 reviews1-bedroom guesthouse w/ full kitchen near DTSJ/SAP
16–23 Jul
Guesthouse in Oakland
4.92 out of 5 average rating, 254 reviewsGuesthouse Garden Retreat
24–31 Jul
Guesthouse in Berkeley
4.99 out of 5 average rating, 129 reviewsBerkeley Bitty House - a little bit of home
15–22 Oct
Guesthouse in San Rafael
4.89 out of 5 average rating, 128 reviewsBeautiful Guesthouse with direct view of the Bay
31 Jul – 7 Aug
Guest house rentals with a washing machine and dryer
Guesthouse in Woodside
4.96 out of 5 average rating, 156 reviewsMountain Retreat
7–14 Sep
Guesthouse in Pacifica
4.98 out of 5 average rating, 370 reviewsNEW Private Studio! Close to SF/SFO/Beach Sanitize
24–31 Aug
Guesthouse in La Honda
4.95 out of 5 average rating, 382 reviewsBicycle Shack @ La Honda Pottery
18–25 Jan
Guesthouse in Redwood City
4.99 out of 5 average rating, 103 reviewsPrivate Cottage near Redwood City and San Carlos Downtowns
26 Feb – 5 Mar
Guesthouse in Redwood City
4.97 out of 5 average rating, 121 reviewsRedwood Casita
6–13 Aug
Guesthouse in Dublin
5.0 out of 5 average rating, 112 reviewsPrivate In-Law unit in Dublin, CA
8–15 Nov
Guesthouse in Oakland
4.99 out of 5 average rating, 160 reviewsRedwood Heights Cottage with Stunning Bay Views
23–30 Nov
Guesthouse in Antioch
4.93 out of 5 average rating, 173 reviewsBeautiful place to rest and clear your mind
14–21 Mar
Quick stats about guesthouse rentals in San Mateo
Total rentals
20 properties
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
20 properties include access to Wi-Fi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Total number of reviews
1.8K reviews
Nightly prices starting at
$51 NZD before taxes and fees
Destinations to explore
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