Vacation rentals in Portola Valley

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Top-rated vacation rentals in Portola Valley

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Top guest favorite

An aerial view captures the spacious outdoor area featuring a private swimming pool, a tennis court, and lush vineyard rows. The home is set amidst trees, with a winding road visible in the background, providing a sense of countryside tranquility.

Home in Portola Valley

4.93 out of 5 average rating, 151 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.

Guest favorite

Guest suite in Woodside

4.81 out of 5 average rating, 222 reviews

Central Woodside suite near restaurants with view

Spacious & peaceful one bedroom suite in central woodside. A nice walk or quick drive to Roberts Market and famous restaurants -Bucks, Village Bakery, Village Pub. Unit has spacious living space w pano view of valley & hills. Steps away from hiking & horse riding trails. 20 mins to SFO 35 mins to San Francisco. Quick 10 min drive to Menlo Park/Palo Alto/Stanford. 15-30 mins to Mountain View, Cupertino, San Jose, etc. This unit is on an entire first floor of a two-story home w own entrance.

Top guest favorite

A wooden walkway is seen nestled among redwood trees, featuring railings with a dark metal finish. The path, made of weathered wood, is surrounded by lush green foliage, providing a natural and serene atmosphere.

Guesthouse in Woodside

4.99 out of 5 average rating, 324 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.

Top guest favorite

A spacious RV is positioned among towering redwood trees, surrounded by gravel pathways. A patio set with a table and chairs provides an inviting outdoor dining area. A shaded umbrella offers protection from the sun, while a hammock rests nearby, enhancing the tranquil forest setting.

Camper/RV in La Honda

4.99 out of 5 average rating, 171 reviews

40 Acre Redwood Forest With Private Trails

We are the descendants of an old San Mateo County pioneer family. We have been passed down and live on a 40 acre redwood forest, backed by 1000 acres of parkland. We would like to share our forest with you. Take a walk and learn of the history behind La Honda's Woodwardia Lodge built in 1913. Walk on private 150 year old logging trails at this historic getaway. Enjoy the natural beauty of the surrounding Redwood forest. Cozy up in a 40' New 2024 RV. All proceeds go to restoring WJS Log Cabin.

Top guest favorite

A small outdoor seating area is presented, featuring two wicker chairs positioned around a round table. Potted plants are placed on the table and nearby, with a patch of artificial grass beneath them. The entrance to the cabin is visible, framed by a welcoming mat.

Cottage in Woodside

4.98 out of 5 average rating, 398 reviews

Kings Mountain Studio Cabin

Enjoy a cozy STUDIO Cabin nestled in the Redwoods up on Kings Mountain. For those who are inclined to have an active lifestyle, We are close to Purisima Creek, Huddart Park, and El Corte De Madera Hiking and Biking Trails. This space is perfect for two! (read more about the space) 20 minutes away from Half Moon Bay with beautiful beaches and 30 min. from Stanford, Palo Alto. We are adjacent to The Mountain House Restaurant. Res recommended. Short drive to local breakfast place. NO PETS!

Guest favorite

A spacious property is nestled among tall, lush trees, with a distinct white exterior. A wide driveway leads to the entrance, complemented by a covered porch area. Natural stone landscaping is visible along the side, blending harmoniously with the surrounding forest.

Guest suite in Woodside

4.88 out of 5 average rating, 382 reviews

Stay Nestled in Ancient Redwoods in Silicon Valley

Welcome to our 6-acre home, High Ground, & have our kid and pet friendly carriage house to yourself! The large studio apt with separate entrance has stunning views of ancient redwood trees + the Bay/Mount Diablo. Immediate hiking trails, wildlife, minutes to: Alice's restaurant (5), Michelin-rated Village Pub (15) highway 280 (15) Palo Alto/Menlo Park/Half Moon Bay/Ocean (30), SFO (35) San Francisco (45). Perfect for a northern CA retreat, business in the Valley or sight-seeing in San Fran.

Superhost

A spacious outdoor deck is surrounded by lush trees, providing a serene setting. Curved seating is arranged in a semi-circle, with light-colored cushions and a colorful blanket draped over one. A patio heater stands nearby, ready for cooler evenings.

Place to stay in Portola Valley

4.87 out of 5 average rating, 146 reviews

Magical 2br/2ba cabins nestled in the redwoods

Nestled into the redwoods of Portola Valley but only 15 minutes from Palo Alto and 25 minutes from SFO, this is a dreamy rustic cabin retreat. We're honored to share it with you. The residence consists of 3 separate cabins built by Yurt People/California Yurts. The cabins are connected by a large deck overlooking a forest creek and enveloped in redwood, oak, and bay trees. You are surrounded by nature and can walk to a large network of public trails. It's a beautiful and magical place.

Top guest favorite

The guesthouse, nestled among tall redwoods, features a wooden exterior with multiple windows allowing natural light to filter in. A welcoming entrance is present, flanked by greenery, while a small raised wooden structure is visible in the foreground, blending harmoniously with the surrounding landscape.

Guesthouse in Woodside

4.97 out of 5 average rating, 263 reviews

SkyHigh Redwoods Retreat with Bay Views

Inhale. Exhale. Relax in this cozy, romantic guesthouse retreat nestled in the redwoods of the Santa Cruz Mountains, overlooking the bay and conveniently located near the famous Alice’s Restaurant on Skyline Blvd in Woodside. The 1 acre gated property has ample parking and privacy. Snuggle in with the wood burning fireplace, prepare meals in the full size kitchen and take in the views of the majestic redwoods right outside the windows with bay views peeking through the trees.

Guest favorite

An outdoor deck features two green cushioned chairs and a wooden table at its center. A potted plant is placed on the table, complementing the natural setting. The entrance door, framed in black, leads into the guesthouse, surrounded by tall trees.

Guesthouse in Portola Valley

4.94 out of 5 average rating, 201 reviews

Woodsy Silicon Valley Cottage

Discover a laid-back side of Silicon Valley in a cozy, cedar-shake guesthouse surrounded by mature trees. Walking distance from a great network of destination hiking and biking trails. 15-30 minutes from Stanford, Sand Hill Road, and major tech companies. This 400 square foot space is on top of our garage and next to our home. There is no public transportation nearby and ride share services are available but not always reliable so you'll need a car.

Guest favorite

Home in Los Altos

4.94 out of 5 average rating, 363 reviews

Silicon Valley Luxury I Sauna, Hot Tub, Pool

Secluded, peaceful 1,500 sq. ft. hillside escape for couples, nature lovers & business travelers. Adjacent to 3,988-acre Rancho San Antonio Preserve with direct trail access & abundant wildlife. Features a fully equipped kitchen, pool table, fireplace, sauna, saline hot tub & pool. Fast fiber-optic WiFi for work & streaming. Prime location: I-280 (1.5 mi), Los Altos dining/shopping (3 mi), Mountain View (5 mi), Cupertino (8 mi), Palo Alto (9 mi).

Guest favorite

A shaded pathway leads through a natural setting, framed by overhanging branches. The surface is composed of wooden boards, providing access to the tranquil surroundings of lush greenery and native shrubs. A sign can be seen in the distance, integrating nature with the landscape.

Guesthouse in Woodside

4.93 out of 5 average rating, 146 reviews

A beautiful Tree house -your own retreat

This charming 2 bedrooms is nestled among the trees in beautiful Woodside, California. This town is 30 minutes from San Francisco and right behind Stanford University. Our tree house is a private, peaceful, modern and very comfortable detached guest house. The house has a fully equip kitchen, BBQ and very peaceful settings where you can enjoy nature hikes and be surrounded by peaceful trees and yet just minutes away from town.

Top guest favorite

The interior of the cabin is shown, featuring a cozy sleeping area with a trundle bed covered in striped bedding. A table with two chairs is visible, and large glass doors lead to a deck area. Natural light enters through the windows, illuminating the soft tones of the walls.

Guesthouse in La Honda

4.95 out of 5 average rating, 436 reviews

Bicycle Shack @ La Honda Pottery

My place is close to miles of hiking and biking trails in county parks and openspace, great views, the beach and not far from the Peninsula, S.F. and Santa Cruz. You’ll love my place because of the location, the people, the ambiance, the outdoors space and that it is a self contained small cabin with a tiny deck.. My place is good for couples, solo adventurers, and furry friends (pets). Perfect for hikers and bikers.