Vacation rentals in Portola Valley

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Top-rated vacation rentals in Portola Valley

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Guest favorite

Guesthouse in Woodside

4.99 out of 5 average rating, 275 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.

Jun 7 – 14

ﺩ.ﺇ1,234 per night

Guest favorite

Cabin in Woodside

4.97 out of 5 average rating, 342 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!

Jul 28 – Aug 4

ﺩ.ﺇ664 per night

Guest favorite

Guest suite in Woodside

4.88 out of 5 average rating, 339 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.

May 28 – Jun 4

ﺩ.ﺇ438 per night

Guest favorite

Guest suite in Redwood City

4.94 out of 5 average rating, 294 reviews

Beautiful Studio

Studio with a private entrance, your own private kitchen, dining area and all cooking utensils, fully equipped. TV 50” with roku, netflix, amazon prime through WiFi. The studio has its own separate heating unit and AC. Bath robes and feather down-quality linen. Well insulated, wheelchair ok Code operated, lock door Minutes away from Stanford. We use eco-friendly cleaning products. Easy parking always available. Comfortable queen bed. Portable cot and bedding available upon request.

Sep 3 – 10

ﺩ.ﺇ454 per night

Guest favorite

Guesthouse in Woodside

4.97 out of 5 average rating, 152 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.

Dec 22 – 29

ﺩ.ﺇ703 per night

Guest favorite

Guest suite in Emerald Hills

4.92 out of 5 average rating, 146 reviews

Elegant retreat in Redwood City

Gorgeous one bedroom apartment with en-suite bathroom, a spacious walk-in closet, ample light, and stunning views. Private fully equipped kitchen and sitting area allow for very comfortable living. Bedroom and sitting area/kitchen are separated by a door to allow for 2 separate work spaces. All furnishings are selected by a professional decorator and routinely upgraded. This is part of a ~4000 sq ft luxury single family home with 2 completely separate and private entrances.

Jan 31 – Feb 7

ﺩ.ﺇ453 per night

Guest favorite

Guesthouse in Portola Valley

4.94 out of 5 average rating, 167 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.

Jun 17 – 24

ﺩ.ﺇ554 per night

Guest favorite

Guesthouse in La Honda

4.95 out of 5 average rating, 381 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.

Jul 25 – Aug 1

ﺩ.ﺇ427 per night

Guest favorite

Guesthouse in Woodside

4.99 out of 5 average rating, 483 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.

Mar 12 – 19

ﺩ.ﺇ760 per night

Guest favorite

Guesthouse in Redwood City

4.94 out of 5 average rating, 173 reviews

Detached Guest House With Views

You'll love this bright studio nestled in the Peninsula hills! It's a very serene spot with beautiful bay and mountain views and a deck. Location is conveniently located close to Silicon Valley and only 25 miles from San Francisco. New bathroom with tile floor, vanity, and new carpet throughout.

Nov 24 – Dec 1

ﺩ.ﺇ520 per night

Guest favorite

Guest suite in Woodside

4.96 out of 5 average rating, 139 reviews

Very Spacious Beautiful Guest Quarter!

Welcome to our mountain home on the “Top of the World” in Woodside, CA and have our spacious guest's quarter with fabulous views of entire Bay Area, furnished with comfortable bedding, and everything you would need for every day comfortable living, just bring in your suit case!

Apr 18 – 25

ﺩ.ﺇ716 per night

Guest favorite

Guesthouse in Sunnyvale

4.96 out of 5 average rating, 386 reviews

Private cottage in a garden

Charming, private backyard studio cottage nestled in a fenced garden in a quiet Sunnyvale neighborhood. Private, clean and cozy, this 240-sq ft space has a kitchenette, bathroom with shower, full-size bed, Wifi, A/C. Short walk to cafes, groceries. Ample parking.

Feb 18 – 25

ﺩ.ﺇ430 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Portola Valley vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Portola Valley's top sights

Alpine Inn Beer Garden13 locals recommend

Windy Hill Preserve45 locals recommend

Amigos Grill Cocina Mexicana y Cantina7 locals recommend

Old Port Lobster Shack16 locals recommend

Roberts Market11 locals recommend

Bianchini's Market30 locals recommend

Other great vacation rentals in Portola Valley

Guest favorite

Home in Portola Valley

4.92 out of 5 average rating, 137 reviews

3 BR Home on Vineyard nr Palo Alto & Stanford

Jun 1 – 6

ﺩ.ﺇ2,092 per night

Guest favorite

Bungalow in Menlo Park

4.98 out of 5 average rating, 178 reviews

Creekside serenity

Sep 1 – 8

ﺩ.ﺇ653 per night

Guest favorite

Guest suite in Palo Alto

5.0 out of 5 average rating, 176 reviews

Savvy Studio ❤︎ Palo Alto ❤︎ of Silicon Valley

Sep 20 – 27

ﺩ.ﺇ499 per night

Guest favorite

Camper/RV in La Honda

4.99 out of 5 average rating, 112 reviews

40 Acre Redwood Forest With Private Trails

Aug 2 – 9

ﺩ.ﺇ566 per night

Superhost

Home in Redwood City

4.88 out of 5 average rating, 180 reviews

NEW! Beautiful Studio/Cottage

Feb 10 – 17

ﺩ.ﺇ465 per night

Guest favorite

Guesthouse in Redwood City

4.93 out of 5 average rating, 296 reviews

Soak up the Serenity on the Patio of a Charming Cottage

Mar 13 – 20

ﺩ.ﺇ399 per night

Guest favorite

Guesthouse in Woodside

4.94 out of 5 average rating, 106 reviews

A beautiful Tree house -your own retreat

Jan 13 – 20

ﺩ.ﺇ1,546 per night

Guest favorite

Guest suite in Woodside

4.89 out of 5 average rating, 408 reviews

Separate entry room near Stanford

Jul 13 – 20

ﺩ.ﺇ585 per night

Show all

Quick stats about vacation rentals in Portola Valley

Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
800 reviews
Nightly prices starting at
ﺩ.ﺇ184 before taxes and fees

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.

Vacation rentals in Portola Valley

Top-rated vacation rentals in Portola Valley

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Portola Valley vacation rentals

Stay near Portola Valley's top sights

Other great vacation rentals in Portola Valley

Home in Portola Valley

Bungalow in Menlo Park

Guest suite in Palo Alto

Camper/RV in La Honda

Home in Redwood City

Guesthouse in Redwood City

Guesthouse in Woodside

Guest suite in Woodside

Quick stats about vacation rentals in Portola Valley

Total rentals

Wifi availability

Rentals with dedicated workspaces

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Portola Valley?

Where should I stay in Portola Valley?

What are the most popular amenities for House Rentals in Portola Valley?

Do house rentals in Portola Valley have a kitchen?

Do house rentals in Portola Valley have wifi?

Are there family-friendly vacation rentals in Portola Valley?

How much does it cost to stay in house rentals in Portola Valley?

Do house rentals in Portola Valley have free parking?

Destinations to explore