Vacation rentals with a pool in San Mateo

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in San Mateo

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Guesthouse in Woodside

4.99 out of 5 average rating, 275 reviews

Rustic Cabin in the Redwoods

Tucked among the redwood trees on top of King's Mountain, this 1 bedroom cabin offers both rustic charm and modern luxury. Property owners live onsite in the main house about 30 feet away from the cabin. Located just 20 minutes off HWY 280, this cabin is the perfect weekend retreat for those looking to get away from the bay area without actually leaving. Spend time relaxing in the pool, hiking or biking one of the nearby trails, or just reading a book while sitting among the redwood trees.

Oct 11 – 18

$294 per night

Guest favorite

Home in Mountain View

4.88 out of 5 average rating, 112 reviews

Little Poolside House near Downtown Mountain View!

Absolutely the best location in Mountain View, steps from Downtown! Situated near all the entertainment, nightlife & attractions this vibrant city has to offer. This beautifully furnished little poolside house is just minutes from the Caltrain & light rail, Shoreline Lake, Stanford, Menlo Park, NASA Ames Center & more! Step outside for a stroll and explore local and international cuisine, wonderful farmers market and shopping! Perfect for family or friends, you will love this Bay Area getaway!

Nov 20 – 27

$136 per night

Guest favorite

Guest suite in San Jose

4.94 out of 5 average rating, 108 reviews

Private Queen Suite-Private Entry, Pool & Hot Tub

Enjoy our newly remodeled private suite and bathroom. Located within a mile of eBay and Netflix plus downtown Campbell and Willow Glen. We follow all cleaning guidelines to protect the health of all guests. We have a professional cleaning crew, so just relax and enjoy. Check-out like a hotel, no starting laundry!You will enjoy a well designed private room with queen bed, private entrance and connected private bathroom in our serene and safe neighborhood. Very high speed internet is included.

Oct 8 – 15

$128 per night

Guest favorite

Guesthouse in Monte Sereno

4.97 out of 5 average rating, 387 reviews

Quiet Poolside Cottage for Solitude

New construction 800 sq. ft. Cottage 1.1 miles to downtown Los Gatos. Off-street parking for one car. Cathedral ceilings with skylight (morning sun, nightly stars). Comfortable pillow top King bed. Single bed in same space for extra guest (extra $25 for third guest/night). Kitchenette with basics. Dining table for work spaces. Pool available for guests. Jacuzzi not available. Many quiet places on property to relax. We do not accept third party reservations. Add your guests on reservation.

Aug 14 – 21

$132 per night

Guest favorite

Guest suite in Woodside

4.89 out of 5 average rating, 408 reviews

Separate entry room near Stanford

This separate entry room opens to a beautiful one-acre garden with a pool, jacuzzi, cable TV/wireless, and parking. We are just off 280 and Woodside Rd., 4 miles from Stanford. It is peaceful and quiet and we are hands-off hosts. There is no access to the house and the room does not have a frig, microwave or dishes. We are set up for independent guests who want to come and go on their own and enjoy local restaurants in Woodside, Palo Alto or RWC. Please note the very short entry door.

Jul 12 – 19

$140 per night

Guest favorite

Guest suite in Walnut Creek

4.99 out of 5 average rating, 490 reviews

Garden Oasis Studio with Spa and Pool, Walnut Creek

How about a rejuvenating get-away with pool and spa? Open the drapes and admire a tranquil garden while enjoying a complimentary beverage. Sunbathe on poolside loungers and ease into a deluxe hot tub. Watch TV from a comfy bed before falling into a restful sleep. Unit deep cleaned. Two separate units on first floor off same foyer; but no shared walls. Private door to Studio. Shared access to spa/pool (9am-11pm) for overnight guests only. 27 stairs outside, 3 inside. Host lives upstairs.

Oct 2 – 9

$133 per night

Guest favorite

Apartment in San Jose

4.98 out of 5 average rating, 223 reviews

Apartment above the valley.

This 2 bedroom apartment. It has outside stairs that lead up to a large private deck (with with spectacular view of Silicon Valley). The entrance is via sliding door from the deck. There are two bedrooms, one bathroom and a combined full kitchen/living room. The ground level pool and patio are shared space with owners. Living room has couch, TV, and Roku streaming. Apartment has good WiFi. Sit on the private deck and you may see wild turkeys, deer, and even a cow!

Feb 14 – 21

$161 per night

Guest favorite

Guesthouse in Los Gatos

4.97 out of 5 average rating, 860 reviews

Cabana in Sierra Azul Open Space Preserve

Nestled in the Sierra Azul Mountain Range in Los Gatos, we enjoy AMAZING unobstructed views of the Entire Silicon Valley... San Francisco to Gilroy from 1700ft altitude! This private retreat is perfect for relaxing and rejuvenating, surrounded by forest, streams and wildlife! Relax in complete solitude, refresh with chemical-free, great tasting spring water and crisp clean air high above the smog of Silicon Valley! Great Hiking/Biking Trails at your backdoor!

Jun 30 – Jul 7

$206 per night

Guest favorite

Guesthouse in San Rafael

4.92 out of 5 average rating, 255 reviews

Mountaintop - Sauna, Pool, Views!

Gorgeous mid-century studio at the top of the hill! You have a studio with private entrance is perfectly situated in Marin County, mid-way between Nor-Cal Wine Country and San Francisco. This is a beautiful area with endless fun and options for your getaway! The first-floor studio in our two-story guest house is remodeled with high-end finishes. Sunny outdoor patio, pool and sauna await with shared sunset overlook; generous space for two people to enjoy!

Dec 13 – 20

$161 per night

Guest favorite

Guesthouse in Walnut Creek

4.91 out of 5 average rating, 502 reviews

Tropical Garden Cottage +HOT TUB &POOL by Downtown

Stylish, beautiful and cosy Guest House in a serene, resort-like setting in Walnut Creek, 25 mile drive/BART from San Francisco downtown, 16 mile from Berkeley/Oakland. Perfectly located in a quiet, safe and green neighborhood: 0.8 mile from Walnut Creek BART station and 1 mile from Walnut Creek downtown, having great restaurants, shopping and other family-friendly activities. The place is not big and is good for couples, solo and business travelers

Feb 9 – 16

$112 per night

Superhost

Home in Burlingame

4.86 out of 5 average rating, 155 reviews

Cozy, Spacious Villa with Private Pool & Bay View!

Set back from an already quite, wide residential street, the closed in the courtyard like creates an added layer of privacy that permeates the entire property. As a single level home with all four bedrooms, clustered together at one end of the house, and one junior suite, two living rooms, a kitchen, and a dining room clustered at the other, this home feels very comfortable on a daily basis, but also very capable for entertaining when needed.

Sep 15 – 22

$835 per night

Guest favorite

Guesthouse in Belmont

4.89 out of 5 average rating, 212 reviews

Private Garden Cottage in Belmont Hills

A fully accessorized cottage in a private and quiet setting at the heart of the San Francisco Bay Area. Newly renovated backyard with always blooming flowers, fruit trees, hot tub, and pool. Regular visits from deer, and professional night illumination make this place feel like a magical forest getaway, quiet and secluded from the surrounding city. Enjoy the multitude of patios for reading and relaxation. We even have a tree house for the kids.

Jan 22 – 29

$221 per night