Holiday 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.

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!

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

Stay in an upscale place that’s near everything you want to visit. This beautiful estate nestled within the Redwood trees, is a 10 min walk to downtown Boulder Creek restaurants and markets. The home has one of the most majestic fireplaces w/vaulted wooden ceilings in Santa Cruz County. Every room has its own private bath. Jacuzzi, tub, swimming pool, front porch, deck, and firepit area. Most recently, the estate served as a filming location for Season 3 of a popular series on Amazon Prime.

Menlo Park 2bd @ Sandhill near 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.

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.

Luxury Silicon Valley Wellness and Work Oasis

Ideal for guests attending matches at Levi’s Stadium, 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.

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.

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.

Large Home in Palo Alto, 5 bedrooms, 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). Close to Levi's Stadium, Stanford and downtown Palo Alto.

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

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.