House vacation rentals in Woodside

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Top-rated house rentals in Woodside

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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, 132 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 light-filled living room features a comfortable white sofa and a stylish armchair, positioned around a wooden coffee table. A modern television is mounted above a decorative stone fireplace. Soft curtains frame the window, enhancing the open feel of the space.
Home in San Mateo
4.87 out of 5 average rating, 113 reviews

10-Min SFO *A/C* Modern Comfort 2BR Family Retreat

Welcome to our beautifully remodeled 2-bedroom home, just minutes from Downtown San Mateo! Whether you’re a couple, a family, or a business traveler, this is the perfect spot for you. Enjoy a fully equipped kitchen, comfortable living space, and kids-friendly amenities. Explore San Mateo's vibrant neighborhoods or take a short drive to San Francisco. We've thought of everything to make your stay comfortable, including fast WiFi and plush bedding. Book now and experience the best of the Bay Area!

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, 171 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
The exterior of the property features a single-story structure with a light gray façade and white trim. A welcoming porch is lined with potted plants, and large windows enhance natural light. A parked vehicle and shaded trees are visible in the surrounding area.
Home in East Palo Alto
4.85 out of 5 average rating, 155 reviews

Newly renovated 2BR/1BA in East Palo Alto

2 bd 1 ba entire unit sharing wall with other units(4 units in the house). Not suitable for people who are too sensitive to privacy . located in city of East Palo Alto ( not part of Palo Alto) , working class neighbor. read” neighborhood ”first. Don’t book if uncomfortable with working class. Only 1 parking spot available, not suitable for guests have 2 cars due to busy street Big floor mirror in 1 bedroom. be caucious if have kids . No oven in the kitchen No party and loud groups allowed

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
4.94 out of 5 average rating, 400 reviews

Silicon Valley Work Retreat | Wellness Oasis

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
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, 377 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

Superhost
The stylish entrance of the home is framed by a well-maintained garden featuring vibrant flowers and mature greenery. A welcoming porch, with a central front door flanked by sidelights, is complemented by a concrete walkway leading to the inviting entrance.
Home in East Palo Alto
4.91 out of 5 average rating, 124 reviews

Newly Remodeled Modern Home

Have fun with the whole family at this stylish place. Newly remodeled stylish home in a convenient location. Close to Stanford, downtown Palo Alto, Meta and Google etc. Parking provided with the property. Full size kitchen with brand new range. Each bedroom has a queen size bed. Extra portable bed or air bed can be added in the living room with extra $30/person per night and early notification. Large private yard great for a family to relax and enjoy the outdoor.

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, 281 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).

Top 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, 242 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 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, 131 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. Conveniently close to downtown San Carlos but feels like you're in the country. FAST WIFI. CLOSE TO 280 AND 101. We will consider pets (additional cleaning fee applies).

Top guest favourite
An open-concept living area features a combination of mid-century furniture and modern design. A cozy sofa and colorful chairs surround a low table, while a dining area with a bright yellow table sits adjacent. Light filters in through large windows, highlighting the space's contemporary aesthetic.
Home in San Mateo
4.95 out of 5 average rating, 134 reviews

Cozy retreat w/ fire pit & atrium

Welcome to your mid-century Bay Area retreat – perfect for families, remote work & relaxed getaways! Enjoy timeless comfort, open spaces & cozy evenings by the fire: - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private backyard w/ fire pit, BBQ & outdoor dining - Enclosed atrium w/ seating & custom mural - Wood-burning indoor fireplace & 42" TV - Full kitchen & dining area - Dedicated workspace & fast wifi - Free parking & self check-in

Guest favourite
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, 370 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

Popular amenities for Woodside house rentals

When is the best time to visit Woodside?

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Avg. price$421 CAD$414 CAD$428 CAD$414 CAD$435 CAD$478 CAD$506 CAD$481 CAD$433 CAD$449 CAD$445 CAD$446 CAD
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Quick stats about house rentals in Woodside

  • Total vacation rentals

    Explore 50 vacation rentals in Woodside

  • Nightly prices starting at

    Woodside vacation rentals start at $56 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,730 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 of Woodside vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, 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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