Vacation rentals with a pool in San Mateo County

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.

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.

Huckleberry Woods Sanctuary: Pool and Spa

Santa Cruz VR permit # 121241. Relax in the serenity of 2 acres in the heart of the redwood forest, plus lush gardens, gated for your security and privacy. A hot tub and direct solar heated pool is just outside your door, with no visible neighbors. It's just a short drive to Santa Cruz's famous beaches, restaurants, and family-friendly activities. We are hosts that live on the same large property, so we can provide local info and quick fixes. Come escape together into our magical forest.

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.

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.

Cozy 2BR w/ Patios, Prime Mountain View Location

Welcome to your perfect Mountain View getaway—an inviting 2-bedroom, 2.5-bath home designed for comfort, convenience, and relaxation in the heart of Silicon Valley. This thoughtfully designed space features two spacious bedrooms each with its own private en-suite bathroom & outside patio, offering privacy and comfort for families, couples, or business travelers. You're minutes away from Downtown Mountain View, Castro street dining, Civic Center, Google, and Caltrain.

King bed Silicon Valley haven w/ pool and parking!

Beautiful and spacious apartment with everything you need: - Ultra-fast fiber optic internet - King bed main bedroom with en-suite bathroom - Free reserved covered parking - Fully stocked kitchen including complimentary coffee/tea/cocoa and cooking essentials - Washer/Dryer In-Unit - Gas Fireplace in Living Room - Ceiling Fans in Dining Area - Modern Appliances & Dishwasher - Sonic Internet Service with speeds up to 10 GB - Large Private Balcony - Pets Welcome

Peaceful Family Friendly Entire 2BR/2BA Apt Unit

Peaceful Family-Friendly retreat in the Belmont hills - Spacious, Quiet, Yet Conveniently Located as a corner unit. This large 2BR, 2BA Entire Apartment is set in a Low-Traffic residential community surrounded by Parks, Hiking Trails, and Nature. 14 minutes from San Francisco International Airport (SFO); minutes from Belmont Downtown and Caltrain, with easy access to Silicon Valley. Convenient to Stanford University and Levi’s Stadium for visits and events.

Your spacious home in Silicon Valley (2bd/2ba)

Relax in a spacious and bright 2 bedroom/2 bath home. Beat the heat - A/C and pool! Queen bed in each bedroom. Well appointed kitchen. washer/dryer, WIFI, Netflix and Amazon Prime, small fenced backyard, HOA pool (seasonal) and green space (great for dogs). 40 minutes to San Francisco. Great location to experience all the Bay Area has to offer! *NOTE* This is my primary home that I am renting out while on vacation. It will have my things in it.

Luxury Silicon Valley Wellness and Work Oasis

Ideal for business travelers, couples, and nature lovers, while staying in a quiet residential setting. Peaceful upscale exclusive use 1,500 sq ft Los Altos Hills retreat beside Rancho San Antonio Preserve. Private trail access. Fast fiber Wi-Fi, workspace, fireplace, sauna, pool table, full kitchen, plush queen bed. Year-round hot tub, BBQ patio, saline pool. Minutes to Stanford, Los Altos, Palo Alto, and major tech campuses, dining and shops.

Timeless Luxury Retreat in a Historic Estate

Welcome to “Manor Retreat” in the heart of Silicon Valley! Take it easy at this tranquil getaway, located in the heart of Silicon Valley! Nestled in a serene historic estate, cottage offers perfect blend of old-world charm and modern comfort. Sip your morning coffee by a historic castle and unwind on a private patio surrounded by nature. After a day of work or exploring, relax in the cozy living space designed for comfort and peace.