Portola Valley Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Portola Valley vacation rentals

@ Marbella Lane - Convenient Home 9-min to Levi's

@ Marbella Lane - Convenient Home 9-min to Levi's
3.0 star property
Sunnyvale
The price is CA $1,218
CA $1,680 total
includes taxes & fees
May 20 - May 21
@ Marbella Lane - Convenient Home 9-min to Levi's

Mays Luxury Farm Stays

Mays Luxury Farm Stays
2.0 star property
Los Gatos
8.8 out of 10, Excellent, (13 reviews)
"Everyone was so friendly! And this place is so peaceful with the birds hobblying around. I def will be back to visit."
United States
Emann
The price is CA $205
CA $330 total
includes taxes & fees
May 20 - May 21
Mays Luxury Farm Stays

Large New Modern Guest House + Laundry + Garden

Large New Modern Guest House + Laundry + Garden
Willow Glen
8.4 out of 10, Very good, (9 reviews)
"Bed is firm and water pressure/temp excellent. Quiet, safe neighborhood that is close to some amazing restaurants. I used the courtyard every day for morning coffee or visits from kids/grandkids. We even did an art project which was a one of those special family memories you talk about for years. We would definitely stay again. "
United States
Raider F.
The price is CA $129
CA $272 total
includes taxes & fees
May 20 - May 21
Large New Modern Guest House + Laundry + Garden

Small Beach Cottage near the Coastal Trail and The Ritz

Small Beach Cottage near the Coastal Trail and The Ritz
Arleta Park
9.8 out of 10, Exceptional, (125 reviews)
"Cottage was quiet and comfortable. Great neighborhood. Amazing setup for dog. Well equiped kitchen and super easy walk to beach."
United States
Paul
The price is CA $263
CA $521 total
includes taxes & fees
May 21 - May 22
Small Beach Cottage near the Coastal Trail and The Ritz

2BR Belmont Treehouse near SFO, Caltrain & Levi's

2BR Belmont Treehouse near SFO, Caltrain & Levi's
Belmont
9.6 out of 10, Exceptional, (8 reviews)
"The place was great! Clean, comfortable, and quiet for my family of 4. It had everything we needed for our 2 week stay so much so that we’ve booked again for another 2 weeks while we are in the middle of a move. Thank you Will!"
United States
Dash L.
The price is CA $217
CA $450 total
includes taxes & fees
May 26 - May 27
2BR Belmont Treehouse near SFO, Caltrain & Levi's

Private Cottage nearby SCU, San Jose Downtown, San Jose Airport, SAP

Private Cottage nearby SCU, San Jose Downtown, San Jose Airport, SAP
Northside
10.0 out of 10, Exceptional, (12 reviews)
"Cottage was perfect for our short stay. Location was convenient and quiet. It was nice to have a washer and a dryer.Host was very responsive and able to accommodate an earlier check-in time."
United States
Kate P.
The price is CA $177
CA $310 total
includes taxes & fees
Jun 11 - Jun 12
Private Cottage nearby SCU, San Jose Downtown, San Jose Airport, SAP

Silicon Valley Hideaway w/ Private Garden

Silicon Valley Hideaway w/ Private Garden
Willow Glen
8.0 out of 10, Very good, (4 reviews)
"We enjoyed the time in your home. We appreciate your hospitality."
United States
Immer L.
The price is CA $85
CA $227 total
includes taxes & fees
May 25 - May 26
Silicon Valley Hideaway w/ Private Garden

Cozy guest suite in Los Gatos - Beach in 30 min!

Cozy guest suite in Los Gatos - Beach in 30 min!
Los Gatos
8.4 out of 10, Very good, (17 reviews)
"Amazing views from the back porch. Very easy to check in and check out. The property is beautiful. Lots of great places nearby to eat, drink, or grab a cup of coffee.Would recommend."
United States
Immanuel D.
The price is CA $164
CA $281 total
includes taxes & fees
May 25 - May 26
Cozy guest suite in Los Gatos - Beach in 30 min!

Palo Alto Cottage: Privacy, Comfort & Convenience

Palo Alto Cottage: Privacy, Comfort & Convenience
Midtown
9.6 out of 10, Exceptional, (18 reviews)
"Quiet, comfortable, and good location. "
United States
Kelsey P.
The price is CA $155
CA $287 total
includes taxes & fees
May 20 - May 21
Palo Alto Cottage: Privacy, Comfort & Convenience

lx51 History in Pescadero

lx51 History in Pescadero
Pescadero
10.0 out of 10, Exceptional, (4 reviews)
"Great location and the backyard was so relaxing. It was a lovely getaway and we look forward to staying there in the future "
United States
jess w.
The price is CA $214
CA $673 total
includes taxes & fees
May 19 - May 20
lx51 History in Pescadero

California Golden Dream C10

California Golden Dream C10
Adobe Meadow
The price is CA $136
CA $205 total
includes taxes & fees
May 21 - May 22
California Golden Dream C10

Gourmet Kitchen + Private Front Yard + Parking

Gourmet Kitchen + Private Front Yard + Parking
Burbank
7.6 out of 10, Good, (20 reviews)
"Great location, clean, friendly owners. "
United States
Brian L.
The price is CA $155
CA $295 total
includes taxes & fees
Jun 8 - Jun 9
Gourmet Kitchen + Private Front Yard + Parking

Luxo Stays |Stanford| 3bd/2ba #pet #comfy

Luxo Stays |Stanford| 3bd/2ba #pet #comfy
East Palo Alto
8.8 out of 10, Excellent, (9 reviews)
"The hosts were attentive the entire duration of our stay. Very appreciative! Thank you! "
United States
Morgan J.
The price is CA $232
CA $710 total
includes taxes & fees
May 20 - May 21
Luxo Stays |Stanford| 3bd/2ba #pet #comfy

Seaside Escape: 1 block to Beach, Private Hot Tub, Fire Pit & BBQ

Seaside Escape: 1 block to Beach, Private Hot Tub, Fire Pit & BBQ
Miramar
9.0 out of 10, Wonderful, (21 reviews)
"Great location, clean and private space."
United States
Alec H.
The price is CA $239
CA $563 total
includes taxes & fees
Jun 1 - Jun 2
Seaside Escape: 1 block to Beach, Private Hot Tub, Fire Pit & BBQ

Downtown Gem: 2BR Historic Spanish Bungalow • Short Walk to SJSU + Parking

Downtown Gem: 2BR Historic Spanish Bungalow • Short Walk to SJSU + Parking
San Jose
10.0 out of 10, Exceptional, (3 reviews)
"Awesome spot!!"
United States
Kevin D.
The price is CA $146
CA $365 total
includes taxes & fees
May 25 - May 26
Downtown Gem: 2BR Historic Spanish Bungalow • Short Walk to SJSU + Parking

Comfortable Room in San Jose with TV, WiFi, mini-fridge,Coffe maker, microwave

Comfortable Room in San Jose with TV, WiFi, mini-fridge,Coffe maker, microwave
San Jose
8.6 out of 10, Excellent, (4 reviews)
"great stay thank you"
United States
Alan G.
The price is CA $88
CA $200 total
includes taxes & fees
May 24 - May 25
Comfortable Room in San Jose with TV, WiFi, mini-fridge,Coffe maker, microwave

San Jose 3b2b near DT & Tech Hub

San Jose 3b2b near DT & Tech Hub
Buena Vista
9.0 out of 10, Wonderful, (19 reviews)
"The house was very well equipped and perfect for our family"
United States
Valentina
The price is CA $296
CA $752 total
includes taxes & fees
May 21 - May 22
San Jose 3b2b near DT & Tech Hub

Private In Law Unit In Beachfront Neighborhood Steps To Sand Walk To Restaurants

Private In Law Unit In Beachfront Neighborhood Steps To Sand Walk To Restaurants
Miramar
7.0 out of 10, Good, (15 reviews)
"Parking was good. Short walk to the trail and beach. Accomodations were acceptable, not spectacular."
Canada
Wilma
The price is CA $69
CA $159 total
includes taxes & fees
May 24 - May 25
Private In Law Unit In Beachfront Neighborhood Steps To Sand Walk To Restaurants

Beautiful 2-Bedrooms Guesthouse Nearby Down Town San Jose

Beautiful 2-Bedrooms Guesthouse Nearby Down Town San Jose
East San Jose
7.6 out of 10, Good, (12 reviews)
"This property met our needs and we enjoyed our stay "
United States
Michelle M.
The price is CA $122
CA $295 total
includes taxes & fees
May 19 - May 20
Beautiful 2-Bedrooms Guesthouse Nearby Down Town San Jose

Central Location + Parking + AC + Kitchen + Wi-Fi 6

Central Location + Parking + AC + Kitchen + Wi-Fi 6
Willow Glen
10.0 out of 10, Exceptional, (3 reviews)
"We had an amazing time it was the perfect location for our vacation. Mr. Wong was very accommodating, made us feel at home and had all the amenities necessary to make our experience pleasant. "
United States
Dawn S.
The price is CA $308
CA $486 total
includes taxes & fees
May 20 - May 21
Central Location + Parking + AC + Kitchen + Wi-Fi 6
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Portola Valley Hotel Reviews

Find out more about Portola Valley

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Portola Valley. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Portola Valley?

Yes, we give you a choice of vacation rentals in Portola Valley close to Labyrinth, or you can choose a secluded option if you're looking for a relaxing stay. Portola Valley is known for its lake views and coffeehouses.

What are some of the best vacation rentals in Portola Valley?

Beachview Holiday Family Retreat | Steps to Sand: This vacation home rental outside of Portola Valley is located on the beach and offers a balcony, Netflix, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Portola Valley?

Choose from 4 Expedia vacation rentals in Portola Valley for a memorable vacation.

What can I see and do in Portola Valley?

Silicon Valley and Santa Cruz Mountains are a couple of lovely local spots to get outside and enjoy nature. Horse Park at Woodside and Thomas Fogarty Winery are other places to visit while you're in town.

What are vacation rentals like in Portola Valley?

Vacation rentals are private accommodations you can stay in for a short or long stay in Portola Valley. Vacation rentals offer amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for a family getaway.