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 favorite

A serene outdoor space features a swimming pool surrounded by lush vegetation and a gently sloping waterfall. Steps lead from the house to the pool area, with a slide positioned nearby. A vineyard is visible in the background, enhancing the tranquil setting.

Home in Portola Valley

4.93 out of 5 average rating, 166 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 favorite

A tranquil pool surrounded by a spacious deck features lounge chairs for relaxation. The sun casts a warm glow over the water, highlighting the adjacent charming cottage and lush greenery. Tall trees provide shade, enhancing the serene atmosphere.

Guesthouse in Oakland

4.97 out of 5 average rating, 269 reviews

Pool, Jacuzzi, Sauna, Huge Views, gated, 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 May 31st to October 30th. 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 favorite

A rustic cabin is situated among tall redwood trees. A wooden deck extends towards a tranquil pool, which is surrounded by greenery and flower beds. The warm tones of the cabin's exterior complement the natural surroundings, enhancing the serene atmosphere.

Guesthouse in Woodside

4.99 out of 5 average rating, 341 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.

Guest favorite

A spacious living area is equipped with a flat-screen TV mounted on the wall and an ornate cabinet. A comfortable grey chair and a glass coffee table are positioned on a soft carpet. Natural light is welcomed through a nearby window, enhancing the cozy atmosphere.

Home in Mountain View

4.89 out of 5 average rating, 174 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 favorite

An outdoor pool area features a long, picturesque pool bordered by vibrant greenery. Large green pool floats rest on the water, complemented by a shaded lounge area under a white umbrella. The space showcases brick pathways and stone details of the home’s exterior.

Home in Los Altos

4.93 out of 5 average rating, 390 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 favorite

The image features a clear pool surrounded by a stone edge, with vibrant orange and purple flowers in bloom along the perimeter. Lush green palm trees and other landscaping elements provide a natural backdrop, creating a serene outdoor setting.

Guest suite in Cambrian

4.96 out of 5 average rating, 171 reviews

Private Queen Suite-Pool & Hot Tub, private entry

Enjoy our newly remodeled private suite and bathroom. Located within a mile of eBay and Netflix plus downtown Los Gatos, Campbell and Willow Glen. Great for Mountain Winery Concerts, 49ers/Levi's Stadium and SJC. 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. Hot tub and Pool are a perfect way to relax and end the evening.

Guest favorite

A spacious bed with an intricate patterned cover is positioned in a well-lit room. Towels are neatly arranged on the bed. A colorful piece of wall art adds a touch of character, while natural light filters through a nearby window.

Guest suite in Woodside

4.89 out of 5 average rating, 457 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.

Guest favorite

A wooden deck is framed by palm trees, featuring a round table and an adjacent chair. The view captures a sparkling pool, surrounded by lush greenery, inviting relaxation in a serene outdoor setting.

Guesthouse in Walnut Creek

4.91 out of 5 average rating, 599 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 favorite

An open-concept living space is highlighted by a modern kitchen featuring light cabinetry and stainless steel appliances. Large windows provide natural light and scenic views. A cozy seating area includes a dark sectional sofa facing a television, and a colorful area rug adds warmth to the floor.

Guesthouse in Walnut Creek

4.96 out of 5 average rating, 123 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

Superhost

A cozy cottage is surrounded by lush greenery and a variety of shrubs. Stairs made of bricks lead up to a welcoming entrance with multiple windows that allow natural light to fill the interior. The setting is serene, with trees enhancing the tranquil atmosphere.

Guesthouse in Belmont

4.87 out of 5 average rating, 263 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 favorite

The modern complex is illuminated under the evening sky, showcasing a resort-style pool surrounded by lounge chairs and umbrellas. A vibrant rooftop area is visible, adorned with greenery and outdoor seating, while soft lights accentuate the building's contemporary architecture.

Apartment in Menlo Park

4.95 out of 5 average rating, 222 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.

Guest favorite

A circular wooden table is surrounded by four stylish chairs under a large umbrella, with a scenic view of the landscape in the background. The inviting pool glistens in the soft light, complemented by lounge chairs positioned nearby and greenery adding a natural touch.

Guest suite in San Rafael

4.91 out of 5 average rating, 337 reviews

Mountaintop poolside suite, sauna, views!

Gorgeous 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! Marin ToT 078730