A tree-lined path with a fence on either side, leading towards a sunset.

Portola Valley Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Portola Valley vacation rentals

A wooden deck with a white bathtub, wooden pergola, and a blue wall with a sign.

1. Mays Luxury Farm Stays

Mays Luxury Farm Stays
3.0 star property
Los Gatos
8.6 out of 10, Excellent, (30 reviews)
"This property is just what you need if you are looking for a peaceful place to escape to in the mountains. The host was very friendly and helpful. The chickens were adorable. And the view was breathtaking. We would definitely come back for another stay."
United States
Adrianna
The price is ￥18,514
￥32,903 total
includes taxes & fees
Oct 5 - Oct 6
Mays Luxury Farm Stays
A wooden deck with a metal railing overlooking a forested area.

2. Cottage In The Woods

Cottage In The Woods
Woodside
10.0 out of 10, Exceptional, (61 reviews)
"We really enjoyed our stay here! One of the best equipped houses we’ve ever rented , and the lovey creek babbling by the porch , it was awesome."
United States
Donna M.
The price is ￥31,456
￥50,723 total
includes taxes & fees
Oct 10 - Oct 11
Cottage In The Woods
A bedroom with a bed, a desk, a chair, a window, and a door.

3. 214A - Cozy Studio with AC & Kitchen near Stanford

214A - Cozy Studio with AC & Kitchen near Stanford
Redwood City
9.2 out of 10, Wonderful, (7 reviews)
"Perfect stay for a quick get away! "
United States
Sylvia L.
The price is ￥14,923
￥29,052 total
includes taxes & fees
Oct 23 - Oct 24
214A - Cozy Studio with AC & Kitchen near Stanford
A modern, well-lit room with a bed, a dining area with a table and chairs, a TV mounted on the wall, and a large window providing natural light.

4. Palo Alto Cottage: Privacy, Comfort & Convenience

Palo Alto Cottage: Privacy, Comfort & Convenience
Midtown
9.6 out of 10, Exceptional, (25 reviews)
"It was a great cozy space and perfect for our trip to the area! Super accessible, but also very private. Absolutely worth the trip here!"
United States
Cera B.
The price is ￥18,574
￥32,862 total
includes taxes & fees
Sep 29 - Sep 30
Palo Alto Cottage: Privacy, Comfort & Convenience
A narrow brick pathway flanked by walls with colorful tile patterns, leading to a doorway.

5. Secluded freestanding house in the delightful grape garden

Secluded freestanding house in the delightful grape garden
Emerald Hills
7.4 out of 10, Good, (8 reviews)
"Location and views were amazing! "
United States
Richelle
The price is ￥21,717
￥53,257 total
includes taxes & fees
Sep 29 - Sep 30
Secluded freestanding house in the delightful grape garden
A two-story house with a gabled roof and a front porch.

6. Modern Guesthouse Retreat in the Heart of Silicon Valley

Modern Guesthouse Retreat in the Heart of Silicon Valley
West Menlo Park
9.2 out of 10, Wonderful, (17 reviews)
"We weren’t actually able to stay at this lovely-looking property, but the hosts were kind and communication was great. "
United States
Anonymous traveler
The price is ￥36,513
￥52,071 total
includes taxes & fees
Oct 1 - Oct 2
Modern Guesthouse Retreat in the Heart of Silicon Valley
A modern kitchen with a central island, bar stools, and a dining area.

7. 2 Beds, 1 Bath, Kitchen private space, Furnished Stanford, Palo Alto, Menlo Park

2 Beds, 1 Bath, Kitchen private space, Furnished Stanford, Palo Alto, Menlo Park
Menlo Park
8.0 out of 10, Very good, (13 reviews)
"Great placeGreat location 10 minutes from everything Palo Alto and Menlo Park"
United States
Christopher W.
The price is ￥22,717
￥47,638 total
includes taxes & fees
Sep 27 - Sep 28
2 Beds, 1 Bath, Kitchen private space, Furnished Stanford, Palo Alto, Menlo Park
A bedroom with a bed, a bedside table with a lamp, a trash bin, and a painting on the wall.

8. @ Marbella Lane - 2BR Guest House |DTWN RWC| Pking

@ Marbella Lane - 2BR Guest House |DTWN RWC| Pking
Palm Park
7.4 out of 10, Good, (20 reviews)
"Nice clean quiet place to spend the night while on a short business trip."
United States
Don
The price is ￥26,988
￥74,573 total
includes taxes & fees
Sep 27 - Sep 28
@ Marbella Lane - 2BR Guest House |DTWN RWC| Pking
A coastal landscape with a sandy beach, cliffs, and a field of wildflowers.

9. Nantucket Penthouse - walk to restaurants, beaches, activies & so much more

Nantucket Penthouse - walk to restaurants, beaches, activies & so much more
South Downtown
9.2 out of 10, Wonderful, (43 reviews)
"The property is clean, convenient, and well-appointed. Owner communication was great. Would rent again in a heartbeat. "
United States
Carmela
The price is ￥6,572
￥56,739 total
includes taxes & fees
Oct 4 - Oct 5
Nantucket Penthouse - walk to restaurants, beaches, activies & so much more
An outdoor patio area with a wooden deck, two wicker chairs, a small table, and a wooden staircase leading to an upper level.

10. Nice one bedroom apartment for short getaways or temporary housing w/ fast WiFi

Nice one bedroom apartment for short getaways or temporary housing w/ fast WiFi
East Palo Alto
8.2 out of 10, Very good, (23 reviews)
"We enjoyed our stay! Great location and perfect for our needs. Will book again!"
United States
Jill J.
The price is ￥20,289
￥46,316 total
includes taxes & fees
Oct 5 - Oct 6
Nice one bedroom apartment for short getaways or temporary housing w/ fast WiFi
A spacious living room with a large wooden coffee table, a sofa with patterned cushions, and a view of the outside through a large window.

11. Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay

Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay
Heritage Downtown
9.2 out of 10, Wonderful, (15 reviews)
"nice place...close to restaurants...easy parking!"
United States
Luz
The price is ￥11,501
￥45,056 total
includes taxes & fees
Sep 30 - Oct 1
Montara Penthouse — Elevated Comfort Above Downtown Half Moon Bay
A bedroom with a bed, a window, an air conditioning unit, and a door leading to another room.

12. Marbella Lane - 3BR House | DTWN RWC | Parking

Marbella Lane - 3BR House | DTWN RWC | Parking
Palm Park
7.4 out of 10, Good, (27 reviews)
"Good location, great house and very spacious "
United States
Anika S.
The price is ￥23,654
￥78,042 total
includes taxes & fees
Sep 28 - Sep 29
Marbella Lane - 3BR House | DTWN RWC | Parking
A modern living room with a grey sofa, green chairs, and a marble coffee table.

13. Mid Century Garden View Home Parking

Mid Century Garden View Home Parking
3.0 star property
East San Mateo
7.2 out of 10, Good, (5 reviews)
"This is a very clean comfortable property! "
United States
Serena
The price is ￥25,032
￥60,307 total
includes taxes & fees
Oct 10 - Oct 11
Mid Century Garden View Home Parking
A bedroom with two beds, a ceiling fan, a window with curtains, and a nightstand with a lamp.

14. Brand New Private One Bedroom Cottage with a Wet Bar/Kitchenette

Brand New Private One Bedroom Cottage with a Wet Bar/Kitchenette
Cupertino
9.6 out of 10, Exceptional, (5 reviews)
"This property is located in a residential and quiet neighborhood with a nice park within walking distance! Great place for someone who is traveling by themselves!"
United States
Kevin
The price is ￥22,018
￥49,649 total
includes taxes & fees
Oct 27 - Oct 28
Brand New Private One Bedroom Cottage with a Wet Bar/Kitchenette
A modern kitchen with white cabinetry, stainless steel appliances, and a herringbone-patterned backsplash.

15. Gourmet Kitchen + Private Front Yard + Parking

Gourmet Kitchen + Private Front Yard + Parking
Burbank
8.2 out of 10, Very good, (33 reviews)
"We had an excellent experience, the property was really clean love the kitchen and the living room area. We loved how peaceful and quiet it was. Communication was fast and easy. shower was too small though . But overall enjoyed the stay"
United States
Sandra
The price is ￥12,541
￥27,864 total
includes taxes & fees
Oct 4 - Oct 5
Gourmet Kitchen + Private Front Yard + Parking
A wooden deck with steps leading to a house with a window and a door.

16. Serene Guest Suite w/ Private Bath and Kitchenette

Serene Guest Suite w/ Private Bath and Kitchenette
Willow Glen
9.0 out of 10, Wonderful, (27 reviews)
"yes great stay"
United States
Alan G.
The price is ￥9,280
￥24,108 total
includes taxes & fees
Oct 5 - Oct 6
Serene Guest Suite w/ Private Bath and Kitchenette
A bedroom with a bed, a bedside table with a lamp, a trash bin, and a painting on the wall.

17. Marbella Lane - 2BR Guest House Dtwn RWC Pking

Marbella Lane - 2BR Guest House Dtwn RWC Pking
3.0 star property
Palm Park
Marbella Lane - 2BR Guest House Dtwn RWC Pking
A cozy bedroom with a wooden ceiling, a bed with white linens, and a textured blanket.

18. 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, (136 reviews)
"Great dog friendly well appointed tiny house."
United States
Deb L.
The price is ￥30,396
￥57,974 total
includes taxes & fees
Oct 6 - Oct 7
Small Beach Cottage near the Coastal Trail and The Ritz
A living room with a sectional sofa, a wooden coffee table, and a colorful striped rug.

19. Affordable Ground Floor Unit In The Heart Of HMB Downtown: Former Mayor's House

Affordable Ground Floor Unit In The Heart Of HMB Downtown: Former Mayor's House
Heritage Downtown
7.8 out of 10, Good, (22 reviews)
"Thanks for a great stay!"
United States
April M.
The price is ￥15,728
￥26,738 total
includes taxes & fees
Oct 27 - Oct 28
Affordable Ground Floor Unit In The Heart Of HMB Downtown: Former Mayor's House
A hotel room with a bed, a desk, a chair, a TV, and a microwave.

20. Remodeled Spanish Bungalow Suite • Short Walk to SJSU + Parking

Remodeled Spanish Bungalow Suite • Short Walk to SJSU + Parking
San Jose
10.0 out of 10, Exceptional, (1 review)
"This was the perfect little stay for me and my pooch. Quiet & clean, nice kitchenette area. The only thing missing is a bathroom sink with mirror. There’s nowhere in the bathroom to wash your face, brush your teeth, put on makeup and get ready for your day. There is a full length mirror, which is great. Cute little sitting outdoor area for morning coffee or afternoon cocktail. One great thing, it’s in a gated area with a very small yard so my dog could be safely contained outside, and it’s...
United States
Asher M.
The price is ￥11,621
￥28,625 total
includes taxes & fees
Oct 7 - Oct 8
Remodeled Spanish Bungalow Suite • Short Walk to SJSU + Parking
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

Bay Landing San Francisco Airport Hotel

Bay Landing San Francisco Airport Hotel

10/10 Excellent
"Good timely airport shuttle. Full breakfast included as well. We were also allowed early check in. Great staff."
Steven 1-night trip
Posted 2 hours ago
Bay Landing San Francisco Airport Hotel

Find out more about Portola Valley

Search for holiday rentals in Portola Valley on Expedia! You can easily find your home rentals, villas, holiday apartments in Portola Valley using one of the methods below:

  • View our selection of featured holiday rentals in Portola Valley
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Look no further and take a look at our great range of rental properties in Portola Valley!

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?

Serene Guest Suite w/ Private Bath and Kitchenette: This vacation home rental outside of Portola Valley has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals will I find in Portola Valley?

Choose from 5 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. In the larger area, you’ll find popular places like Levi's Stadium and SAP Center at San Jose.

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.