Holiday 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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Superhost

Condo in Mountain View

4.95 out of 5 average rating, 135 reviews

Spacious Top Floor Condo Retreat

Listen to the calming sounds of all the water features throughout the property from the secluded balcony. Inside, relax in 1000 square feet of upscale surroundings that include wood floors and high quality Tempur-Pedic king mattress. Later, head for the ground-floor pools and hot tub. 1000 sq ft of space on the top floor. Queen size adjustable firmness air mattress with clean beddings available upon request to be set up in the living room. You will be able to access the entire unit, 2 Swimming pools, and the hot tub. I will be available by text, phone or email throughout the stay. The quiet and beautiful setting is surrounded by trees. Within walking distance to CalTrain station, San Antonio shopping center, and Whole Foods, Trader Joe, movie theater plus numerous boutiques. Major tech companies located nearby include G00gle and Faceb00k. Stanford University is within a 10 minute drive. A short 5-10 minute walk to the Cal Train stop but the unit is not impacted by any train noise. The bus stop is conveniently around the corner to take you to Downtown Castro Street or Stanford University and beyond.

Top Guest favourite

Home in Portola Valley

4.94 out of 5 average rating, 160 reviews

3 BR Home on Vineyard nr Palo Alto & Stanford

Professionally cleaned detached home nestled among an oak grove, waterfall & vineyard in the hills above Stanford (10 min), Palo Alto (20 min), Menlo Park (10-20 min), Mountain View (25 min) and San Francisco and San Jose. Perfect for families and groups; staycations, off-sites or startups visiting Silicon Valley . See resort-style amenities below. LATEST UPGRADES: better AC, faster internet & WiFi6 for lots of devices & bandwidth. Pickleball lines on tennis court; putting green w/ remote tees.

Top Guest favourite

Guesthouse in Woodside

4.99 out of 5 average rating, 335 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.

Top Guest favourite

Home in Mountain View

4.9 out of 5 average rating, 165 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!

Guest favourite

Home in Los Altos

4.93 out of 5 average rating, 376 reviews

Pool, Hot tub, Sauna I Your Silicon Valley Luxury

Upscale Los Altos Hills. Peaceful and spacious 1,500 sq. ft. retreat. Ideal for business travelers, couples, nature lovers. Adjacent to 3,988-acre Rancho San Antonio Preserve with direct trail access, wildlife, serenity. Inside: workspace with fiber-optic Wi-Fi, fireplace, sauna, pool table, fully equipped kitchen and plush queen bed with guest praised mattress. Outside: exclusive access to saline heated pool and hot tub, patio with BBQ. Minutes from Stanford, Palo Alto, and top tech campuses.

Top Guest favourite

Guesthouse in Oakland

4.97 out of 5 average rating, 256 reviews

82 “ Pool, Jacuzzi , HOT SAUNA, VIEWS, Newer ADU!

Stunning, ADU cottage w/ higher end finishes. Endless VIEWS of mountains set on a beautiful, peaceful, upscale gated, property surrounded by redwood, pine & oak trees. 1 mile to large regional parks for hiking, mountain biking and horse stables. Nature at its best! Pool heated 82F May 1st-Oct. 31st. 16 miles to San Francisco, 5-10 minutes to many restaurants. New Jacuzzi and outdoor sauna. Large patio, pool / deck (6500 sq foot outdoor oasis shared with main house with a small family of 4)

Top Guest favourite

Guesthouse in San Rafael

4.97 out of 5 average rating, 172 reviews

Hillside Oasis Btwn SF, Napa w/ Big Views + Pool!

Welcome to your retreat! Drive through the gate to a peaceful setting. Sunset from your private deck in the hills above San Rafael. It's like a treehouse but with no stairs! Stay home all day (guests love the bed!) or visit the adorable towns and famous hikes of Marin. 45 mins to Napa/Sonoma or 15 min to San Francisco - experience the best of the Bay from here. Happy to help you plan. Separate building from main house. TV: Netflix, Hulu, Disney+ & more! Pool heated May - August.

Guest favourite

Guesthouse in Walnut Creek

4.96 out of 5 average rating, 116 reviews

The Willow Cottage

Modern Farmhouse Cottage, walking distance to downtown Walnut Creek. Recently renovated unit sits on a sprawling 5 Acres, which feels like the country but also close to shopping and amazing restaurants. Includes full access to a pool, Chef style kitchen and an outdoor lounge area. Private entrance and plenty of free parking. If Interested, please contact me with: - Occupancy (total amount of guests, pets, cars, etc) - A bit about yourself and your interest in renting

Top Guest favourite

Guest suite in Walnut Creek

4.99 out of 5 average rating, 598 reviews

Garden Oasis Suite with Spa and Pool, Walnut Creek

How about a rejuvenating get-away with pool and hot tub? Relax on a patio lounger overlooking a tropical garden. Enjoy an evening snack while watching a movie. Super comfy bed and separate living room. Deep cleaned. 2 separate units off same foyer; but no shared walls. Private locked unit door. Shared access to spa/pool (9am-11pm) for overnight guests only. 27 stairs to reach house. Host lives upstairs. Complimentary beverage for 3+ nights. After 10 stays, $100 credit.

Top Guest favourite

Guesthouse in Almaden Valley

4.97 out of 5 average rating, 986 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!

Superhost

Guesthouse in Belmont

4.88 out of 5 average rating, 253 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.

Guest favourite

Apartment in Menlo Park

4.94 out of 5 average rating, 216 reviews

Spacious & Luxurious 1 BR w/Pool & Free Parking

Welcome to our Luxurious 1 bedroom located in Menlo Park! Our unit is situated in the luxurious Anton Menlo Apartments, which boasts a range of amenities for our guests to enjoy during their stay. Our unit features a spacious and fully furnished living area, comfortable Queen size bed, with a large modern bathroom, and a fully equipped kitchen with all the necessary appliances and cookware to prepare your favorite meals.