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House holiday rentals in Woodside

Find and book unique houses on Airbnb

Top-rated house rentals in Woodside

Guests agree: These houses are highly rated for location, cleanliness and more.

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Guest favourite
A spacious bedroom features large windows dressed with sheer white curtains, allowing natural light to fill the space. A comfortable bed is accompanied by two elegant chairs positioned beside a small table. The warm wooden flooring complements the calming atmosphere.
Home in San Carlos
4.95 out of 5 average rating, 131 reviews

Serene Oasis in the midst of Silicon Valley

Gaze out at the beautiful green canyon while having a morning coffee in bed. Head to the fully equipped kitchen to prepare breakfast and enjoy it outside on the balcony, surrounded by the sights and sounds of this stunning hilltop location. Close to 280. Centrally located in Silicon Valley for easy access to both San Jose and San Francisco. Deck/BBQ Lounge Area. Minimal. Enjoy life in the San Carlos hills. Drive about 5 minutes to lively San Carlos downtown for several restaurants and bars. Go hiking in Edgewood, Crestview, or Big Canyon. For a taste of big city life, adventure a bit further to San Francisco. Driving is the best option, I280 and 101 are easily accessible. Cal Train station down the hill - connects all the way from San Francisco to San Jose. Very spacious unit ( approximately 1200 sq.ft )

Guest favourite
A serene outdoor space features a swimming pool surrounded by lush vegetation and a gently sloping waterfall. Steps lead from the house to the pool area, with a slide positioned nearby. A vineyard is visible in the background, enhancing the tranquil setting.
Home in Portola Valley
4.93 out of 5 average rating, 169 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.

Superhost
A bright living room features a light-colored sofa adorned with a mix of blue and cream pillows. A large art piece in soft colors hangs above a modern coffee table. A potted plant adds greenery, while natural light flows in through a window.
Home in Redwood City
4.92 out of 5 average rating, 153 reviews

🌞Sunny house with♨️hot tub near🌲Stanford

- Sunny, private backyard with an outdoor table and a hot tub - Easy self check-in and check-out - Dedicated off street parking on the driveway and in the garage - Walking distance to Selby's, a Michelin star restaurant - Fast wifi and desks in each bedroom - Modern, professionally designed interior with central heat and air conditioning - 8 min drive to Stanford University - Easy access to HW 101, El Camino and within mins to Menlo Park and Downtown Redwood City, Caltrain, Costco, Whole Foods.

Guest favourite
An outdoor pool area features a long, picturesque pool bordered by vibrant greenery. Large green pool floats rest on the water, complemented by a shaded lounge area under a white umbrella. The space showcases brick pathways and stone details of the home’s exterior.
Home in Los Altos
4.93 out of 5 average rating, 397 reviews

Pool, Hot tub, Sauna I Your Silicon Valley Luxury

Upscale Los Altos Hills. Peaceful and spacious 1,500 sq. ft. retreat. Ideal for business travelers, couples, nature lovers. Adjacent to 3,988-acre Rancho San Antonio Preserve with direct trail access, wildlife, serenity. Inside: workspace with fiber-optic Wi-Fi, fireplace, sauna, pool table, fully equipped kitchen and plush queen bed with guest praised mattress. Outside: exclusive access to saline heated pool and hot tub, patio with BBQ. Minutes from Stanford, Palo Alto, and top tech campuses.

Guest favourite
Home in East Palo Alto
4.96 out of 5 average rating, 420 reviews

Huge Suite w/ own bathroom, patio, dining, office

Forget your worries in this spacious & serene space. Large Private Suite w/ office zone, dining table, private patio w/ furniture, indoor & outdoor showers & dining, large walk-in closet. Super fast & reliable wifi. Vaulted ceilings, skylights, ceiling fans, & beautiful artwork. The suite located at back of a spacious home shared w/ 2 other suites. Walkable distance to large shopping center. Centrally located close to Stanford U & Hospital, Tech Companies & Freeways to entire Bay Area

Guest favourite
A large window showcases a view of lush trees and a serene outdoor area. Natural light floods the space, enhancing the warm tones of the elegant decor, which includes a small decorative bicycle and a floral arrangement on a nearby table.
Home in Belmont
4.93 out of 5 average rating, 376 reviews

Hidden French Gem for Fam/Biz~near Caltrain,SFO

Highly welcome respectful travelers to step through the 750ft super quiet European-style private studio with secluded bay view. Curl up in front of the 4K TV for movie nights at this stylish, soundproofed nest with a luxury mattress, washer and dryer! — welcome infant & kids. — Read everything to avoid surprises. — 5 min walks to park, Caltrain/restaurants; 10~13 min drive to SFO/Stanford; 20-25 min SF. — No pets, no smoking/vaping, no party! — book for 3 if need single bed

Top Guest favourite
The guest house is presented with a charming Tudor-style exterior, featuring a pitched roof and decorative wooden beams. Large glass doors provide a view into the interior space, framed by a covered porch supported by sturdy beams. Lush landscaping and a vibrant red entry gate enhance the inviting ambiance.
Home in San Carlos
4.96 out of 5 average rating, 280 reviews

The Perfectly Appointed Modern English Guest House

Relax and unwind in this newly constructed guest house. Completed in 2019 it offers all the amenities of a 5-star hotel suite with the privacy and ambiance of a quaint English Tudor home. Located just 2 blocks from charming downtown San Carlos in the “City of Good Living”. We are 30 minutes from San Francisco, San Jose and the beach in Half Moon Bay —with easy access to Highways 101 and 280, as well as public transportation (SamTrans, Caltrain and BART via Caltrain).

Guest favourite
A spacious bedroom features a wooden bed frame with a comfortable queen mattress and quality linens. A flat-screen TV is mounted on the wall, and a wooden dresser is positioned nearby. Soft lighting illuminates the room, highlighting the tasteful decor and calming color palette.
Home in Woodside Plaza
4.91 out of 5 average rating, 241 reviews

The Chandelier Studio

Newly remodeled with private bathroom, kitchenette, and entry. Located in one of the most desirable areas of Redwood City known as Woodside Plaza. This is a quiet and pleasant community with tree line streets. We offer a very comfortable and spacious studio, quality linens, YoutubeTV, Netflix, Amazon Prime, Roku, Wifi. Equipped with central AC and Heater. Comfortable queen bed. Minutes away from Stanford hospital Futon converts to extra bed, bedding available.

Guest favourite
A bright sleeping area features a gold bed frame with crisp white linens. An accent pillow adds a pop of color. A nightstand holds a small lamp, while a window displays greenery outside, enhancing the inviting and serene ambiance of the room.
Home in San Mateo
4.95 out of 5 average rating, 133 reviews

Stylish 3BR retreat w/ fire pit & patio

Welcome to your Bay Area mid-century retreat – a peaceful, light-filled home perfect for families, remote workers & weekend getaways! - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private backyard w/ fire pit, BBQ & outdoor dining - Enclosed atrium w/ custom mural & red maple tree - Open living area w/ wood-burning fireplace - Full kitchen & dining area - Dedicated workspace w/ fast Wi-Fi & parking included

Superhost
A spacious mini studio is featured, showcasing a comfortable bed with a white bedspread. A desk and chair are positioned against the wall, accompanied by a microwave and a water boiler. The private bath area is visible in the background, and natural light brightens the room.
Home in Mountain View
4.9 out of 5 average rating, 365 reviews

391-2 Mini studio in the heart of Silicon Valle

Separate entrance Private bath Comfortable and relaxing settings Walking distance to San Antonio shopping center and Whole Foods store Plenty of nearby restaurants Street Parking only 6 minute walk to 7-11 store, Chinese restaurant and laundry 10 minute walk to Bus/Shuttle stops 11 minute walk to Cal Train station 15 minute drive to Stanford University 15 minute drive to G**gle campus

Guest favourite
A spacious deck is showcased, featuring a vibrant red umbrella providing shade over a circular table. A hammock with colorful stripes is visible, gently swaying in the sunlight. Surrounding greenery creates a serene backdrop, enhancing the outdoor relaxation spaces.
Home in San Carlos
4.81 out of 5 average rating, 130 reviews

Canyon Oak House: Private, tranquil with trees

Looking for a serene getaway in San Carlos/mid peninsula? Tranquil, professionally cleaned retreat with lots of breathing space perched among the trees in Devonshire Canyon, San Carlos, CA. Enjoy evening sun on the large deck, wake up to the birds in the trees or a family of deer in the garden. FAST WIFI. CLOSE TO 280 AND 101. We will consider pets (additional cleaning fee applies).

Top Guest favourite
A coastal cabin is situated on rugged cliffs overlooking the ocean. The structure features large windows, allowing for expansive views of the water. Lush greenery surrounds the home, highlighting its natural setting against a cloudy sky.
Home in Montara
5 out of 5 average rating, 111 reviews

Sea Wolf Bungalow

If you're looking for the most spectacular views on the San Mateo Coast, come to Sea Wolf Bungalow. Located just 20 minutes southwest of San Francisco and 7 miles north of Half Moon Bay, this historic cabin sits on its on own point with sweeping views of the Pacific. Enjoy whale watching, the beach, surfing, fishing, golf, hiking and the fabulous dining of the coastal area.

Popular amenities for Woodside house rentals

When is the best time to visit Woodside?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$533 NZD$524 NZD$542 NZD$524 NZD$551 NZD$606 NZD$642 NZD$610 NZD$549 NZD$569 NZD$563 NZD$565 NZD
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Quick stats about house rentals in Woodside

  • Total holiday rentals

    Explore 50 holiday rentals in Woodside

  • Nightly prices starting at

    Woodside holiday rentals start at $71 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,730 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Woodside holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Woodside rentals

  • 4.9 Average rating

    Woodside stays are highly rated by guests—averaging 4.9 out of 5!

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