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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.

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Guest suite in East San Jose

4.87 out of 5 average rating, 688 reviews

Hillside Retreat Private 2-Room Guest Unit & Pool

Our home is on 1/2 acre hilltop lot, in a secluded, very quite cul-de-sac, with easy access to major freeways, minutes from SJC airport, downtown, SAP, SJSU, convention center. This listing is for an entire separate unit, attached to main house. It features 2 rooms with private yard and pool to yourself. You are free to relax in the back yard with view, surrounded by mature trees, hummingbirds, butterflies while surf the net, or swim in our solar thermal heated pool when weather permitted.

Guesthouse in Woodside

4.99 out of 5 average rating, 305 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.

Home in Mountain View

4.9 out of 5 average rating, 133 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!

Guesthouse in Stinson Beach

4.93 out of 5 average rating, 471 reviews

Romantic Creekside Cottage

Your cottage escape awaits! Set against the backdrop of the mountains and facing the Pacific, our lovely, romantic cottage is waiting for you to enjoy. Open your doors to the sounds of birdsong, ocean waves and cascading water. Watch the sunset from "The Kissing Bench" and sip your morning coffee in your patio. Light a fire and curl up with a book. When you are ready to step out, a few minutes down the path will bring you straight to town, the beach and the trails of Mt. Tamalpais.

Guest suite in Willow Glen

4.94 out of 5 average rating, 127 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.

Guesthouse in Monte Sereno

4.98 out of 5 average rating, 410 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.

Guest suite in Woodside

4.89 out of 5 average rating, 428 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.

Guesthouse in Walnut Creek

4.91 out of 5 average rating, 533 reviews

Tropical Garden Cottage +HOT TUB &POOL by Downtown

Stylish, beautiful and cozy Guest House in a serene, resort-like setting in Walnut Creek, 25 mile drive/BART from San Francisco downtown, 16 mile from Berkeley/Oakland, 50 mile from Napa Valley Wineries. 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.

Guest suite in Walnut Creek

4.99 out of 5 average rating, 521 reviews

Garden Oasis Studio with Spa and Pool, Walnut Creek

Former Plus-rated unit. How about a rejuvenating get-away with pool and spa? Picture window overlooking tranquil garden. Sunbathe poolside and ease into a deluxe hot tub. Watch TV from a comfy bed before falling into a restful sleep. Complimentary beverage for 3 nights or more. Deep cleaned. Two separate units 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.

Rental unit in Evergreen

4.98 out of 5 average rating, 244 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!

Guesthouse in Almaden Valley

4.97 out of 5 average rating, 933 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!

Guesthouse in San Rafael

4.93 out of 5 average rating, 281 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!

Vacation rentals for every style

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Popular amenities for San Mateo rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Willow Glen

4.81 out of 5 average rating, 190 reviews

Beautiful Large 4BR Home with POOL

Home in San Rafael

4.92 out of 5 average rating, 49 reviews

Fully renovated private cul-de-sac home in Marin

Home in Ben Lomond

4.94 out of 5 average rating, 125 reviews

Socially Distant yet Closein; Meadow, Hot Tub, Pet

Home in Willow Glen

5 out of 5 average rating, 43 reviews

The Seahorse of Willow Glen with pool/spa

Home in Tiburon

5 out of 5 average rating, 8 reviews

Unreal Beachfront Marin Getaway!

Home in Atherton

4.88 out of 5 average rating, 8 reviews

Home in Atherton, Menlo Park

Home in Discovery Bay

4.95 out of 5 average rating, 85 reviews

Waterfront home w/ private dock, pool, NEW jacuzzi

Home in San Jose

4.86 out of 5 average rating, 125 reviews

Beautiful 3BD Home w/ Heated Pool and Fire Pit

Condo rentals with a pool

Condo in South of Market

4.8 out of 5 average rating, 15 reviews

Massive 1-bedroom condo in the heart of SF

Condo in Downtown Oakland

4.92 out of 5 average rating, 268 reviews

Lakeside Retreat (w/ private parking)

Condo in Mission Bay

4.93 out of 5 average rating, 40 reviews

Luxury Condo ~ Iconic Waterfront & City View in SF

Condo in Foster City

4.89 out of 5 average rating, 18 reviews

Spacious 2 b2b great location+ pool+ works spaces

Condo in Mountain View

4.94 out of 5 average rating, 33 reviews

Luxury Condo near Giants & Stanford Tech

Condo in San Rafael

5 out of 5 average rating, 5 reviews

Modern, bright 2 bedroom/1 bath 2nd story

Condo in San Jose

5 out of 5 average rating, 7 reviews

Charming 2 bedroom 2 story condo

Condo in Mountain View

4.95 out of 5 average rating, 124 reviews

Spacious Top Floor Condo Retreat

Quick stats about vacation rentals with a pool in San Mateo

Total rentals
90 properties
Total number of reviews
790 reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wifi availability
90 properties include access to wifi

Destinations to explore