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Vacation rentals in Portola Valley

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Top-rated vacation rentals in Portola Valley

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guesthouse in Redwood City

4.93 out of 5 average rating, 300 reviews

Soak up the Serenity on the Patio of a Charming Cottage

Light the fire pit and dress for dinner in the vine-covered garden at a peaceful retreat with a soothing waterfall. Zen beachy decor and coastal paintings set the scene indoors, with abundant natural light enhancing easy open-plan living. Pets are welcome with a small cleaning fee of a $50 (one time fee) and additional pets $25 (one time fee). The main room is 12'x17'. Closet is 6 1/2' long. Bathroom 4'x5 1/2' + shower 3'3" x 3'3". kitchen 4 1/2' x 8". Simple breakfast served. Your own private entrance, plenty of parking on the street, nice neighborhood. We are available if you have any questions or need information on the area. 2 night minimum please. The cottage is tucked away off the street in a quiet, safe neighborhood where residents walk their dogs in pleasant weather. Nearby downtown Redwood City is home to shops and groceries and freeways and public transportation are within easy reach. There is a bus that runs at the corner of our block, it would take you to downtown Redwood City or travel down the El Camino Real. There is a train depot downtown as well. Pets - 2 small dogs in the main house, 2 outdoor cats.

Guesthouse in Woodside

4.99 out of 5 average rating, 308 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.

Camper/RV in La Honda

4.99 out of 5 average rating, 149 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.

Cottage in Woodside

4.98 out of 5 average rating, 372 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 suite in Woodside

4.88 out of 5 average rating, 365 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.

Place to stay in Portola Valley

4.88 out of 5 average rating, 129 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.

Guest suite in Woodside

4.89 out of 5 average rating, 431 reviews

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.

Guesthouse in Woodside

4.97 out of 5 average rating, 210 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.

Guesthouse in Portola Valley

4.94 out of 5 average rating, 191 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.

Guesthouse in Woodside

4.93 out of 5 average rating, 129 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.

Guesthouse in La Honda

4.95 out of 5 average rating, 412 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.

Guesthouse in Woodside

4.99 out of 5 average rating, 515 reviews

Guest House in the Woods

Our guest house is located close to La Honda and Woodside in the North Santa Cruz Mountains. Located in the Redwood forest and looks down onto a beautiful creek from a lovely deck. There are many open space hiking and biking trails within a short drive, and the beach. 5 miles from Alice's Resturant. San Francisco and Santa Cruz are easily accessible. The house has vaulted ceilings and a full kitchen, and laundry.

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Popular amenities for Portola Valley vacation rentals

Free parking on premises

Air conditioning

Stay near Portola Valley's top sights

Alice's Restaurant65 locals recommend

Wunderlich County Park46 locals recommend

Windy Hill Preserve45 locals recommend

Stanford Dish41 locals recommend

Pearson-Arastradero Preserve30 locals recommend

Bianchini's Market30 locals recommend

Other great vacation rentals in Portola Valley

Rental unit in Pedro Point-Shelter Cove

4.81 out of 5 average rating, 765 reviews

Luxury Beach View Apartment

Home in Woodside

4.94 out of 5 average rating, 84 reviews

Redwood Forest Retreat

Guest suite in Boulder Creek

4.89 out of 5 average rating, 969 reviews

Redwood Riverfront Getaway

Guesthouse in Atherton

4.99 out of 5 average rating, 191 reviews

Charming Cottage near Stanford in Lovely Garden

Guesthouse in Redwood City

4.88 out of 5 average rating, 189 reviews

Modern Studio Cottage with Private Entrance

Guesthouse in Mountain View

4.96 out of 5 average rating, 278 reviews

Private studio in downtown

Cottage in Redwood City

4.94 out of 5 average rating, 95 reviews

Adorable Garden Cottage near Stanford

Guesthouse in Redwood City

4.97 out of 5 average rating, 141 reviews

Redwood Cottage

Quick stats about vacation rentals in Portola Valley

Total rentals
20 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
900 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Portola Valley?
Yes! Work meets play with ease at over 10 vacation rentals in Portola Valley featuring dedicated workspaces. Stay connected and productive in your home away from home.
Where should I stay in Portola Valley?
Make yourself at home in Portola Valley by choosing from our most frequently booked neighborhoods. We have over 230 vacation rentals in Portola Valley Ranch, and over 230 vacation rentals in Central Portola Valley.
What are the most popular amenities for House Rentals in Portola Valley?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a kitchen, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Portola Valley have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Portola Valley. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Portola Valley have wifi?
Absolutely! We offer over 10 house rentals with wifi in Portola Valley. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Portola Valley?
Portola Valley has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Portola Valley?
Experience the best of Portola Valley with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Portola Valley have free parking?
Absolutely! We offer over 10 house rentals with free parking in Portola Valley. Enjoy a tailored experience with all the comforts you desire.

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