Vacation rentals with a pool in San Mateo County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in San Mateo County

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

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Guest favorite

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.

Guest favorite

A cozy bedroom is furnished with a spacious bed layered with a comforter. A desk, chair, and lamp are positioned nearby, illuminated by natural light from a large window. A minimalistic artwork is displayed on the wall, adding a gentle touch of color.

Apartment in Mountain View

4.81 out of 5 average rating, 26 reviews

Big Room w/ private bath & work desk in DT Mt View

Welcome to your cozy home nestled in the quiet neighborhood in the heart of Mountain View, Downtown, Castro St. You will get a private bedroom, private bathroom - Breakfast of coffee, breads & yogurt. (Microwave available) - High-speed wifi, laundry, Designated workspace area - A parking spot and patio - Access to pool, hot tub, BBQ - 3 min walk to all restaurants/bars & Starbucks - 12 min walk to Caltrain St, 2 min to El Camino Real -Delicious Indian home cooked meals available on request

Top guest favorite

A serene swimming pool reflects the clear blue sky, surrounded by lush landscaping. Natural stone steps lead to the house, flanked by vibrant foliage and small waterfalls, creating a tranquil retreat.

Home in Portola Valley

4.94 out of 5 average rating, 164 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 area is surrounded by lush greenery and rustic wooden structures. The clear water reflects the trees and sunlight above. A wooden deck offers space for relaxation, while adjacent seating arrangements and a grill provide options for outdoor enjoyment.

Guesthouse in Woodside

4.99 out of 5 average rating, 338 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

An aerial view of the modern Vasara complex showcases the inviting resort-style pool surrounded by palm trees. The building's sleek architecture and large windows reflect a vibrant communal atmosphere, contributing to a dynamic living environment in a prime location.

Apartment in Menlo Park

4.82 out of 5 average rating, 17 reviews

Studio Near Meta: Pool, Spa, Gym + Resort Living!

This modern studio in the luxurious Vasara complex is perfect for business travelers, just minutes from Meta HQ & major tech hubs. Stay productive with a dedicated workspace, ergonomic chair, monitor, & high-speed Wi-Fi. Unwind at the cozy kotatsu table after a long day. Enjoy a fully equipped kitchen & exclusive resort-style amenities: pool, spa, gym, bocce ball & clubhouse. A secure parking spot with free EV charging adds extra convenience to your stay. Perfect for work, play, and relaxation.

Top guest favorite

A tranquil pool area is highlighted by a circular swimming pool surrounded by colorful blooming flowers. Two red lounge chairs are positioned beside the pool, inviting relaxation under the clear sky. Lush greenery and wooden fencing provide privacy, enhancing the outdoor setting.

Home in Mountain View

4.9 out of 5 average rating, 168 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, 387 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

A spacious outdoor pool area is depicted, featuring a large swimming pool surrounded by lounge chairs with blue cushions. Umbrellas provide shade, and a modern clubhouse is visible in the background, along with lush landscaping and tall trees creating a serene atmosphere.

Apartment in Menlo Park

5 out of 5 average rating, 34 reviews

Menlo Park 2bd @ Sandhill nr Stanford - Pool, Gym

Welcome to this beautifully designed 2 bedroom 2 bath home with everything you need, including surprise and delight details throughout. Located right off Sand Hill Road and just over a mile from Stanford University, Stanford Medical Hospital, and Stanford Shopping Center. Just beyond is Caltrain and Downtown Palo Alto. Enjoy amenities like our year-round heated pool, hot-tub, and fitness center. This ground-floor unit has a private patio perfect for lounging and enjoying California weather.

Guest favorite

A well-maintained garden pathway leads to a pool area surrounded by lush greenery. Tropical plants and vibrant flowers add color to the landscape, while a variety of trees provide shade. The tranquil setting invites relaxation with the pool visible in the background.

Guest suite in Woodside

4.89 out of 5 average rating, 455 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.

Superhost

Guesthouse in Emerald Hills

4.78 out of 5 average rating, 40 reviews

A freestanding casita in a delightful grape garden

Escape to a secluded retreat featuring a queen bed plus spacious sectional sofa that can sleep another two, total four people. The ambiance of a wine country getaway with a sprawling yard, heated pool and rejuvenating spa. Enjoy the picturesque setting reminiscent of a lush vineyard. Shower bathroom. Kitchenette with two-hot plate, microwave, dishwasher, coffee maker, tea pot. Take advantage of the salt water pool, spa, and outdoor area exclusively available for your enjoyment.

Guest favorite

A modern living area is presented with a comfortable sectional sofa and stylish coffee table. A large window offers views of the outdoors, while plants and decorative elements enhance the inviting ambiance. Soft lighting illuminates the space, creating a serene environment.

Condo in East Palo Alto

5 out of 5 average rating, 10 reviews

Modern 2BR Condo | Business & Long-Term Stays

🛏 2BR/2BA | Fast WiFi | Fully Furnished | Pool & Gym Stay in this fully furnished, modern 2BR condo perfect for business travelers & long-term stays! Enjoy a quiet, work-friendly space with: ✅ High-speed WiFi ✅ King & Queen beds w/ premium linens ✅ Full kitchen + in-unit laundry ✅ On-site parking + secured entry ✅ Access to gym, pool & hot tub 📍 Prime location: 10-15 min to Google, Meta, Stanford & hospitals. 🔹 30+ day stays preferred. Message for corporate discounts!

Superhost

A spacious living area features high, A-frame ceilings adorned with wooden beams. Large windows allow natural light to flood the room, revealing a grand piano and a comfortable sofa. A soft area rug lies on the polished wooden floor, creating a warm and inviting atmosphere.

Home in Brisbane

4.89 out of 5 average rating, 108 reviews

Luxurious Bayview Treehouse: Hot Tub, 15 min to SF

Immerse yourself in an architectural gem that balances modern elegance and rustic allure. Our four-bedroom, three-bathroom sanctuary is your secluded escape amidst expansive greenery, a canvas for unforgettable moments. Just 10 minutes from SFO Airport and 15 minutes from dynamic San Francisco, our home is your launchpad to exploration. The Bay Bridge graces the view from your private balcony and hot tub, framing your stay with an awe-inspiring vista.