
Holiday rentals with a pool in San Mateo County
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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.

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.

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.

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.

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.

Camellia Cottage with Pool View
Reminiscent of a 1920's Hollywood villa, enjoy the aesthetics of that romantic age, yet experience 5 star luxury pampering & the most modern of comforts. Explore and relax in the tranquil natural surroundings this 4-acre oak studded estate has to offer, a tropical conservatory, perfect pool and infinity edge spa. Close to Woodside downtown, Highway 280, Silicon Valley, Sand Hill VC firms, Stanford University and Hospital. A short drive to San Francisco. SFO and SJC are only 25 minutes away.

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.

The Hacienda- Santa Cruz Mountain Ridgetop Retreat
"Welcome to the Hacienda", a modest mid-century retreat located in the beautiful Santa Cruz Mountains. The Hacienda is located just 5 minutes from Ben Lomond town, 10 minutes from Henry Cowell State Park and only a 20 minute drive from Santa Cruz beaches. Our unique private home includes a pool & hot tub which sits on the ridgetop overlooking the gorgeous San Lorenzo Valley. If you're looking for peace & tranquility or simply need to relax and recharge, the Hacienda awaits your arrival.

Zen Japan-inspired Suite - Resort hot tub/pool/gym
Step into tranquility with this beautifully designed Japanese-inspired studio, featuring traditional tatami flooring and a low Nectar king bed that offers a peaceful and restful sleep. This cozy space seamlessly blends the timeless elegance of Japanese minimalistic design with the convenience of modern amenities (hot tub, pool). Enjoy an oversized bathroom / shower, fully-equipped kitchen with modern GE appliances (Vitamix), making it perfect for both short stays and longer retreats.

Large Home in Palo Alto w/Pool
This large 5 bedroom and 3 bath home in Palo Alto has plenty of room for big groups and families. The home features 1 king bed, 3 Queen beds, 2 twin beds and a Queen pull-out sofa sleeper. The kitchen is beautiful and well equipped and this large home has plenty of room for everyone to relax. Enjoy the manicured backyard with large deck, BBQ and sparkling pool (w/child safety fence; pool/hot tub not heated). Located near Stanford, downtown Palo Alto, wonderful parks and restaurants.

King Bed Fully Furnished 1 Bed 1 Bath By Stanford
800 Sq feet | 75 Sq meters Modern 1-bedroom 1-bathroom luxury apartment in an ultra-modern building, featuring resort-style amenities and all the essential conveniences. Highlights: ➡ Spacious 1 bedroom with full kitchens and private bathrooms ➡ 1 King Bedroom ➡24-hour state-of-the-art fitness center ➡ Commuter’s dream location is just a short drive from major tech companies: Meta, G00gle, Ápple ➡ 25-minute drive from San Francisco and San Jose

Modern 4bd/3ba w/ pool In Downtown MV
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 home with swimming pool is just minutes from Caltrain & light rail, Shoreline Lake, Stanford, Menlo Park, NASA & more! New HVAC installed Oct 2023. Step outside for a stroll and explore local and international cuisine, farmers market and shopping! Shared pool.

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.
Popular amenities for San Mateo County rentals with a pool
House rentals with a pool

4-5 bedrm, 4-5 bath luxury home with pool, hot tub

Fab Family Home in the Hills

Mission style, w. Pool, Hot tub, walk to downtown

Life Home

Charming family house in a Great location

Casita McAlvarez

Nuby's Bed & Breakfast (SCC Permit #251085)

Upscale 5BR w/ Pool, KTV, Near Stanford & SF
Apartment rentals with a pool

Luxury loft by the water

KING BED | Fully Furnished Luxury Condo Gym & Pool

Entire 1BR Apt•Bright, Clean, Spacious & All Yours

Contemporary 2BR - Blocks from Stanford Campus

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Contemporary 2BR Apt in Silicon Valley
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