Holiday rentals with a pool in Hillsborough

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.

Tropical Garden Cottage +HOT TUB &POOL by Downtown

Stylish, beautiful and cozy Guest House in a serene, resort-like setting in Walnut Creek, 25 mile drive/BART from San Francisco downtown, 16 mi from Berkeley/Oakland, 50 mi from Napa Valley Wineries. Perfectly located in a quiet, safe and green neighborhood: 0.8 mi from Walnut Creek BART station and 1 mi from Walnut Creek downtown, having great restaurants, shopping and other family-friendly activities. The place is not big, has rustic charm and is good for couples, solo and business travelers.

Heated Pool, Jacuzzi, Sauna, Huge Views, Chic ADU!

Tucked between pine, oak, & redwood trees is a 4 year old, high end cottage nestled with amazing views of the mountains. Peaceful, upscale gated, property. 1 mile to large regional parks for hiking, mountain biking & horse stables. Nature at its best! Pool heated to 82F 4/1-10-31. 16 miles to San Francisco, 5-10 minutes to many restaurants. Jacuzzi & barrel sauna, grill. Large patio, pool /new deck (6500 sq foot outdoor oasis shared with main house small family of 4). Own spot in driveway.

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.

Private cul-de-sac home in Marin with pool

Fully renovated 2-bedroom, 1.5-bathroom home with 3 beds, central AC, strong wifi, family-friendly amenities, private pool, and putting green in Gerstle Park, San Rafael, CA. Short walk to parks, tennis / pickle ball court, restaurants, bars, and shops. 30-minute drive to San Francisco, Berkeley, or Wine Country. Whether it's sightseeing, wine tasting, or local cuisine you're seeking out, we've got you covered. *Loud music + parties are prohibited **Pool is only accessible Apr - Oct

MCM Waterfront Pool/Hot Tub between SF and Napa

Mid Century Modern-MCM Time Capsule right on San Francisco Bay! 15 minutes to Golden Gate Bridge, 30 minutes to wineries. All original architectures and features. Stunning property! To make sure our house fits your needs PLEASE click on “Show more below and read our entire listing as well as the "House Rules" and "Safety & property" sections at the very bottom of this page before sending us a booking request. We live in a quiet neighborhood and have strict noise limits after 10pm!!

Poolside Retreat with Views • Private Guesthouse

Private hillside retreat with sweeping views, heated pool (May–Sep) & a standalone guesthouse all to yourselves. Ideal for couples & families seeking a peaceful escape - minutes from Marin's trails, charming towns & easy day trips to San Francisco, Napa, Sonoma. Enjoy a getaway with the confidence of a top 1% local Superhost, personal recommendations, and a curated guidebook to help you experience the very best of the area. Marin's 1st Green Business Certified vacation rental.

Lafayette Treehouse - Relax and Rejuvenate

Relax and rejuvenate your spirit in this uniquely designed home, situated under a canopy of sprawling oaks. It has incredible panoramic views of Mt. Diablo and the surrounding valley, and multiple areas to relax. Hang out on the deck with a glass of wine, take a dip in the refreshing salt-water pool, or just melt away in our therapeutic cave spa. Centrally located in the East Bay just minutes from Lafayette, Walnut Creek, Berkeley and ~35 minutes from San Fran.

Sanctuary in Sierra Azul Open Space Preserve

Nestled in the Sierra Azul Mountain Range in Los Gatos, the Sanctuary combines rustic country decor, original art and spa amenities, providing the perfect private retreat. Surrounded by numerous hiking trails, many friendly animals, and vast wild forest all around us to explore to your liking, along with this exclusive unit serves to provide a refreshing, rejuvenating space to reconnect with your loved one, yourself and of course Mother Nature!

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.

Luxury 2BR Apt near Tech Companies and Stanford

Welcome to our Luxurious 2 bedroom located in Menlo Park! Our unit is situated in the luxurious Anton Menlo Apartments, which boasts a range of amenities for our guests to enjoy during their stay. Our unit features a spacious and fully furnished living area, two comfortable bedrooms both with queen size bed, a pair of modern bathrooms, and a fully equipped kitchen with all the necessary appliances and cookware to prepare your favorite meals.