Holiday 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 favourite

Apartment 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 favourite

Flat in Mountain View

4.96 out of 5 average rating, 25 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 favourite

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 favourite

Guest house 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 favourite

Flat 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 favourite

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 favourite

Home in Los Altos

4.93 out of 5 average rating, 385 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

Flat 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 favourite

Guest suite in Woodside

4.89 out of 5 average rating, 454 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

Guest house in Emerald Hills

4.77 out of 5 average rating, 39 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 favourite

Cabin in Woodside

4.95 out of 5 average rating, 19 reviews

Guesthouse in woodside -

This private guest house is located on one of the most prestigious properties in Woodside with it's own private entrance & setting on a 1.5 acre lot. Includes living room, 1 queen bedroom, sofa bed, kitchen and private patio - * There are 15 stairs from where the car is parked to the guest house. Access to basketball court and play structure. No access to the pool/hot tub/fire pit. Close to restaurants, 2 mins from 280 HW, 3 mins to downtown Woodside, 10 mins to Stanford University.

Guest favourite

Apartment 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!