Vacation rentals in Portola Valley

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Top-rated vacation rentals in Portola Valley

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Guest favourite

Home in Portola Valley

4.92 out of 5 average rating, 137 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.

Jan. 28 – Feb. 4

$699 CAD per night

Guest favourite

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 21 – 28

$170 CAD per night

Guest favourite

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.

Dec. 10 – 17

$205 CAD per night

Guest favourite

Guesthouse in Woodside

4.97 out of 5 average rating, 151 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. 16 – 23

$302 CAD per night

Guest favourite

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.

Dec. 6 – 13

$209 CAD per night

Guest favourite

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.

Sep. 29 – Oct. 6

$274 CAD per night

Guest favourite

Guesthouse in La Honda

4.95 out of 5 average rating, 380 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.

Jan. 4 – 11

$165 CAD per night

Guest favourite

Guesthouse in Woodside

4.99 out of 5 average rating, 481 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.

Feb. 13 – 20

$326 CAD per night

Guest favourite

Condo in Redwood City

4.93 out of 5 average rating, 102 reviews

Cozy Entire 1-Bedroom Condo in Redwood City

Beautiful condo, offering peace, comfort and privacy for your travel needs. Great location for couples, families, solo & business travelers. Family friendly neighborhood, peaceful, clean and safe. Professionally maintained and cleaned. Close to boutiques, coffee, restaurants, parks, downtown redwood city & just a few minutes from Palo Alto. Easy access to San Francisco, San Jose and the Silicon Valley.

Sep. 5 – 12

$285 CAD per night

Guest favourite

Guest suite in Redwood City

4.96 out of 5 average rating, 137 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!

Dec. 15 – 22

$290 CAD per night

Guest favourite

Bungalow in Menlo Park

4.98 out of 5 average rating, 178 reviews

Creekside serenity

Beautiful cottage in natural creekside setting minutes from Stanford and Hwy 280. Clean, comfortable, private and contemporary with WiFi, HDTV with streaming and generous closet and drawer space. Stanford Dish hiking just steps away. Ample parking. 30 day minimum stay.

Sep. 1 – 8

$253 CAD per night

Guest favourite

Guest suite in Menlo Park

4.88 out of 5 average rating, 104 reviews

New studio apt--walk to Stanford

Lovely compact studio apartment (adjoining but totally separate from our 2-bedroom guest cottage). Nice, private setting, on a private driveway, away from the street. Approx 215 square feet (20 square meters). Please note this is a one-guest space. Thank you!

Nov. 22 – 29

$160 CAD 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 favourite

Guesthouse in Redwood City

4.94 out of 5 average rating, 173 reviews

Detached Guest House With Views

Oct. 25 – Nov. 1

$226 CAD per night

Guest favourite

Cabin in Woodside

4.97 out of 5 average rating, 342 reviews

Kings Mountain Studio Cabin

May 31 – Jun. 7

$281 CAD per night

Guest favourite

Guest suite in Woodside

4.89 out of 5 average rating, 408 reviews

Separate entry room near Stanford

May 17 – 24

$228 CAD per night

Superhost

Guest suite in Los Altos Hills

4.8 out of 5 average rating, 147 reviews

A private hillside suite nestled among oaks

Jun. 21 – 28

$238 CAD per night

Guest favourite

Guesthouse in Sunnyvale

4.96 out of 5 average rating, 386 reviews

Private cottage in a garden

Dec. 7 – 14

$188 CAD per night

Guest favourite

Guesthouse in Woodside

4.99 out of 5 average rating, 275 reviews

Rustic Cabin in the Redwoods

May 28 – Jun. 4

$473 CAD per night

Guest favourite

Guesthouse in Redwood City

4.93 out of 5 average rating, 296 reviews

Soak up the Serenity on the Patio of a Charming Cottage

Dec. 12 – 19

$173 CAD per night

Guest favourite

Guesthouse in Woodside

4.94 out of 5 average rating, 102 reviews

A beautiful Tree house -your own retreat

Jul. 23 – 30

$563 CAD 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	$69 CAD before taxes and fees

Vacation rentals in Portola Valley

Top-rated vacation rentals in Portola Valley

Home in Portola Valley

Guest suite in Woodside

Guest suite in Redwood City

Guesthouse in Woodside

Guest suite in Emerald Hills

Guesthouse in Portola Valley

Guesthouse in La Honda

Guesthouse in Woodside

Condo in Redwood City

Guest suite in Redwood City

Bungalow in Menlo Park

Guest suite in Menlo Park

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

Guesthouse in Redwood City

Cabin in Woodside

Guest suite in Woodside

Guest suite in Los Altos Hills

Guesthouse in Sunnyvale

Guesthouse in Woodside

Guesthouse in Redwood City

Guesthouse 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

Destinations to explore