House vacation rentals in Woodside

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Top-rated house rentals in Woodside

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Guest favorite

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, 128 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 )

Top guest favorite

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

4.94 out of 5 average rating, 165 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.

Top guest favorite

A spacious bedroom features a wooden sleigh bed with light bedding. A dark wood dresser is positioned beside the bed, complementing the room's neutral carpet and walls. Natural light enters through two windows, enhancing the room's calm atmosphere.

Home in Menlo Park

4.94 out of 5 average rating, 99 reviews

3BR Near Stanford, Bonus Room, No Cleaning Fee

Welcome to our bright, relaxing home conveniently near Stanford University and Hospital. The home has 3 bedrooms -- the main one with a king-sized bed -- and 2 bathrooms, a spacious living area, a formal dining area, and a bonus work area, perfect for working from home. The kitchen comes with all the appliances and kitchenware you need. There is also a spacious backyard and a grill for you to enjoy. Located in West Menlo Park you're within striking distance of Stanford, Sand Hill Road, Menlo

Guest favorite

A modern craftsman-style house is illuminated at night, featuring a prominent wooden front door framed by soft landscape lighting. Tall shrubs and carefully arranged path lighting guide the way to the entrance, accentuating the home's charming architectural details.

Home in Crescent Park

4.95 out of 5 average rating, 255 reviews

Palo Alto Modern Retreat

This 3 bed, 3 bath Modern craftsman in the very heart of Silicon Valley is an easy 5 minute walk to the shops, restaurants and offices that dot University Avenue in downtown Palo Alto. Arriving and departing CalTrain's Palo Alto University Avenue station is easily done with a 10 minute walk. You really don't need a car but the driveway easily handles 3 cars. Rest assured, you'll sleep in quiet comfort. ----- Note: This house has a no parties or events policy. No outdoor noise after 9:30 PM.

Guest favorite

Home in Los Altos

4.93 out of 5 average rating, 388 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.

Top guest favorite

The kitchen area showcases a wooden island with bar stools, illuminated by pendant lights. Large windows allow natural light to fill the space, highlighting the unique wallpaper and eclectic art pieces in the background.

Home in East Palo Alto

4.96 out of 5 average rating, 419 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 favorite

Home in San Mateo

4.95 out of 5 average rating, 130 reviews

Mid-century retreat w/ firepit & patio

Welcome to your Bay Area retreat in San Mateo’s tranquil Highlands neighborhood. Relax by the wood-burning fireplace, gather around the fire pit under the stars, and enjoy easy access to both nature and the city. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Enclosed atrium w/ mural & red maple tree - Pvt backyard w/ fire pit, BBQ & 8-person dining - Fully equipped kitchen w/ stainless appliances - 42” TV w/ streaming & wood-burning fireplace - 15 min to SFO, 20 min to San Francisco

Guest favorite

Two comfortable chairs face the ocean, positioned on a stone patio with a small wooden table between them. A glass railing provides an unobstructed view of the serene Pacific Ocean, framed by lush greenery on the side.

Home in Moss Beach

4.93 out of 5 average rating, 257 reviews

Walk to the Beach from this Ocean Front Home

Your beachfront escape awaits you. Come immerse yourself in the serenity of this Pacific Ocean retreat gracefully set in a secluded beach just 25 mins south of San Francisco. This 2 bed / 2 bath home features breathtaking ocean views and direct beach access just a few steps down. The hot tub overlooking the ocean, fire pits and a putting green complete this idyllic space. Comfortably sleeps 4 adults on 2 king beds and 2 high quality airbeds are provided for total sleeping for 6.

Top guest favorite

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, 273 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 favorite

Home in Woodside Plaza

4.91 out of 5 average rating, 234 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 favorite

Home in Half Moon Bay

4.96 out of 5 average rating, 135 reviews

Beach Cottage Near Coastal Trail & Ritz

This adorable coastal house features a 5 minute walk to the ocean and borders wide open spaces with luscious views to the south. It is a two, bed two bath house with a den that sleeps five people. If you want to get away from it all, watch the falcons play in the sky, the humming buzz around our bottle brush tree flowers and listen to the waves crash just beyond the bluffs -- this is your spot. Your pup will enjoy a fully fenced in yard. Rarely available.

Top guest favorite

A welcoming entrance is framed by greenery, with a stone pathway leading to a decorative wooden door featuring an oval glass panel. Vibrant red and green foliage adds a colorful touch to the surrounding landscape.

Home in Cupertino

4.94 out of 5 average rating, 279 reviews

2BR House + Patio + Office near Apple and Main St.

Spacious 2BR + private office in a quiet, walkable neighborhood. 600+ Mbps fiber Wi-Fi, two private parking spots, and a fully stocked kitchen. Just a 3-minute walk to 6 restaurants, 7-minute walk to Cupertino Main Street, and 2-minute drive to Hwy 280 and Lawrence Expressway. Includes two queen beds, smart TVs with streaming, and a backyard garden patio. Perfect for remote work or a comfortable Bay Area stay.