Portola Valley Holiday Rentals

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Our top choices for Portola Valley holiday rentals

Aparthotel in Santa Clara

Kasa University-Airport Santa Clara
4.0 star property
9.0 out of 10, Wonderful, (56)
"The unit was spacious, clean, and comfortable. The location is close to SAP Center. There’s a cafe downstairs. Otherwise you need to drive for eateries."
United States
Quynh Huong
The price is AU$183
includes taxes & fees
8 Jan - 9 Jan 2026
Kasa University-Airport Santa Clara
9.4 out of 10, Exceptional, (37)
"The stay was great, would recommend for quick getaway. "
United States
Kiera E.
Nantucket Penthouse - walk to restaurants, beaches, activies & so much more
10.0 out of 10, Exceptional, (9)
"This was a fantastic place to stay, exactly as the pictures showed it to be. Would definitely stay here again!"
United States
Deirdre S.
The price is AU$319
includes taxes & fees
12 Jan - 13 Jan 2026
Private Cottage nearby SCU, San Jose Downtown, San Jose Airport, SAP

Holiday Home in East San Mateo

Mid Century Garden View Home Parking
2.0 star property
8.8 out of 10, Excellent, (3)
"This is a very clean comfortable property! "
United States
Serena
The price is AU$568
includes taxes & fees
4 Jan - 5 Jan 2026
Mid Century Garden View Home Parking
9.8 out of 10, Exceptional, (8)
"Great place "
United States
Marie S.
The price is AU$417
includes taxes & fees
19 Jan - 20 Jan 2026
Mavericks Penthouse – Downtown Luxury on Main Street, Half Moon Bay
7.6 out of 10, Good, (15)
"Loved the kitchen and the neighborhood. Close to the rose garden neighborhood and the Rosicrucian Museum. Great place to stay. "
United States
Sherry R.
The price is AU$265
includes taxes & fees
2 Jan - 3 Jan 2026
Gourmet Kitchen + Private Front Yard + Parking
10.0 out of 10, Exceptional, (3)
"It was well located we were able to find our way around town. It had a great walk in shower , was cute and met our needs very well"
United States
Debra H.
The price is AU$388
includes taxes & fees
2 Jan - 3 Jan 2026
Large Private Oasis with Yard Space, Minutes to Downtown
8.2 out of 10, Very good, (11)
"We had a wonderful stay at Eric's lovely home. The view is not to be believed, and the rooms were comfortable and clean. We hope to return as soon as possible. Thanks Eric!"
United States
Susan & David S.
The price is AU$304
includes taxes & fees
2 Jan - 3 Jan 2026
Cozy guest suite in Los Gatos - Beach in 30 min!
9.6 out of 10, Exceptional, (10)
"Beautiful and great! Friendly hosts"
United States
C D.
The price is AU$319
includes taxes & fees
1 Jan - 2 Jan 2026
Palo Alto Cottage: Privacy, Comfort & Convenience
The price is AU$14,079
includes taxes & fees
1 Jan - 2 Jan 2026
Spacious estate near charming downtown Saratoga and the Montalvo Arts Center.
9.4 out of 10, Exceptional, (10)
"Very nice and cozy stay. We felt safe and had easy access to the SAP center where we attended a concert. "
United States
Lizbeth
The price is AU$228
includes taxes & fees
11 Jan - 12 Jan 2026
Serene Guest Suite w/ Private Bath and Kitchenette
2.0 star property
10.0 out of 10, Exceptional, (1)
"Our stay was a short one while we were visiting our daughter who lives less than a mile away. We spent most of our time at our daughter’s house and really only slept at this property. It was very clean and well-stocked in a great neighborhood and within walking distance of a number of great eateries and small shops. "
United States
Christiane J.
The price is AU$486
includes taxes & fees
1 Jan - 2 Jan 2026
RainierADU · Spacious CRTL San Jose 1B w/crib free street prkg
9.8 out of 10, Exceptional, (113)
"Great and cosy surfers cottage...my son and I were in HMB to attend a wedding."
United States
Charles C.
The price is AU$442
includes taxes & fees
13 Jan - 14 Jan 2026
Small Beach Cottage near the Coastal Trail and The Ritz
8.6 out of 10, Excellent, (4)
"Clean, simple, well stocked!"
United States
Ben
The price is AU$257
includes taxes & fees
1 Jan - 2 Jan 2026
214A - Cozy Studio with AC & Kitchen near Stanford
9.8 out of 10, Exceptional, (8)
"Ideal location, walking distance from popular San Jose points of interest. House had a great layout and style. Would stay there again."
United States
Liberato M.
The price is AU$412
includes taxes & fees
6 Jan - 7 Jan 2026
Airy Modern 2BR/2BA - Parking + Laundry + Sleep 6
2.0 star property
The price is AU$227
includes taxes & fees
2 Jan - 3 Jan 2026
Luxury Private Bedroom steps from DT Mt View
2.0 star property
10.0 out of 10, Exceptional, (7)
"Beach nearby. Very clean and nice vacation rental. The hosts really care about their guests and it shows. "
United States
Angela
The price is AU$478
includes taxes & fees
4 Jan - 5 Jan 2026
Modern Coastal Retreat, Walk to Downtown HMB & Beach
10.0 out of 10, Exceptional, (5)
"Good clean property and check in was easy"
United States
Brij P.
The price is AU$242
includes taxes & fees
6 Jan - 7 Jan 2026
"Queens Palace" Studio Apt Business Ready - San Jose
10.0 out of 10, Exceptional, (63)
"Great location. I have stayed here multiple times and this is an excellent choice. Highly recommend."
United States
Bob N.
The price is AU$312
includes taxes & fees
2 Jan - 3 Jan 2026
Private Willow Glen Studio Guesthouse
9.6 out of 10, Exceptional, (20)
"Beautiful home with large bedrooms and a great kitchen area! Extremely clean! Owner had great communication the whole time. Will definitely be staying there again!!"
United States
Garrett W.
The price is AU$1,854
includes taxes & fees
1 Jan - 2 Jan 2026
W. Menlo Luxurious executive mansion over 4000sqft
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.
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Top Portola Valley Hotel Reviews

Find out more about Portola Valley

Everything you need to know about Portola Valley holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Portola Valley holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Portola Valley holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Portola Valley holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Portola Valley. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Portola Valley holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Portola Valley holiday rentals we have selected for you start as low as AU$183 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Portola Valley rentals

At Expedia, we put the best Portola Valley holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Portola Valley rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Portola Valley holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Portola Valley. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Portola Valley?

Yes, there are holiday rentals close to the most popular sights in Portola Valley, or you can select a more secluded option if you're looking for a relaxing stay. Portola Valley is known for its lake views and coffee shops.

What are some of the best holiday rentals that Portola Valley has to offer?

Marbella Lane Triplex San Jose: This holiday home rental outside Portola Valley has a TV and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware.

How many holiday rentals will I find in Portola Valley?

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

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 holiday rentals like in Portola Valley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Portola Valley. Holiday rentals offer extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.