House holiday rentals in Woodside

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Top-rated house rentals in Woodside

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

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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
4.91 out of 5 average rating, 161 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.

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, 287 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
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, 409 reviews

Luxury Silicon Valley Work & Wellness Oasis

PLEASE CONTACT US FOR SUN–THU DISCOUNTS (2+ NIGHTS). Peaceful upscale 1,500 sq ft Los Altos Hills retreat beside Rancho San Antonio Preserve with private trail access. Ideal for business travelers, couples, and nature lovers. Fast fiber Wi-Fi, dedicated workspace, fireplace, sauna, pool table, full kitchen, plush queen bed. Year-round hot tub, BBQ patio, heated saline pool May–Oct. Minutes to Stanford, Los Altos, Palo Alto, and major tech campuses, dining and shops.

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, 245 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.

Top 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, 133 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
The studio apartment features an open layout, showcasing a full kitchen with wooden cabinetry and a dining area. A comfortable window seat offers serene views, while light wood flooring adds warmth to the space. Modern lighting fixtures complement the overall aesthetic.
Home in Montara
4.98 out of 5 average rating, 375 reviews

A private beachy pad in Montara

Welcome to Chez Sage! Your own private apartment get-away, with a private deck and ocean views, is just 30 minutes south of San Francisco. The entrance to your private apartment leads you up the stairs to a deck with an ocean peek. Enter your home away from home and relax in the window seat to gaze at Montara Mountain or eat breakfast on the island with peeks of the ocean. Once you're settled, it's just a short stroll to watch the sunset from the beach.

Guest favourite
A cozy living room displays two red armchairs facing a blue sofa adorned with decorative pillows. Natural light filters through the large windows, highlighting the hardwood floor. A television is mounted on a wooden stand beside a bookshelf, with artwork depicting trees hanging on the wall.
Home in San Carlos
4.98 out of 5 average rating, 148 reviews

New!! Silicon Valley Charming 3B2B House Fast wifi

Beautiful fully furnished home with magnificent bay views. Located in the heart of Silicon Valley -- 15-20 mins drive away from SFO. Beds and linens are new and very comfortable. Kitchen includes new stainless steel appliances. The house is walking distance to highly rated downtown restaurants and shops and to Caltrain station with service to San Francisco and Silicon Valley. It is perfect place for family visit, business trip and team retreat.

Top guest favourite
A vibrant yellow dining table set for eight is positioned in a spacious open-plan area, surrounded by natural light from large glass doors. A soft, textured light fixture hangs overhead, complementing the modern aesthetic. The backdrop features a landscaped outdoor space visible through the glass.
Home in San Mateo
4.95 out of 5 average rating, 139 reviews

Super Bowl Wknd Sleeps 6 Easy Drive to Santa Clara

Visiting for Super Bowl weekend? Welcome to your calm Bay Area retreat - a cozy space for relaxed days & fireside evenings. Enjoy comfort, privacy & easy indoor-outdoor flow: Sleeps 6 | 3 bedrooms | 3 beds | 2 baths Wood-burning fireplace & fenced backyard w/ fire pit Enclosed atrium w/ custom mural Kitchen, dining area & dedicated workspace Free parking, Wi-Fi & laundry Single level home w/ private entrance

Top guest favourite
A charming exterior view of the home is highlighted, featuring a well-maintained lawn and manicured landscaping. Large windows allow natural light to enter the interior, and patio seating is arranged outside for relaxation. The peaceful setting is complemented by surrounding trees.
Home in Palo Alto
4.91 out of 5 average rating, 140 reviews

Tranquil private 2 BR home in Palo Alto/Stanford

This two bedroom home is perfect for an Executive or visiting Scholar. Convenient location to Stanford Hospital / University, Stanford Shopping Centre , Tesla, SAP, VM Ware. Palo Alto School District. You’ll love my place because of the location on 1/3rd of an acre, very private and quiet with beautifully manicured grounds. The home is fully furnished, all you need do is walk in with your suitcase!

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, 376 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

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
4.99 out of 5 average rating, 118 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.

Superhost
A modern studio layout features a kitchen with sleek appliances, including a built-in oven and microwave. A comfortable seating area with a sectional sofa faces a gas fireplace and a wall-mounted TV. Large windows allow natural light to illuminate the space.
Home in East Palo Alto
4.86 out of 5 average rating, 228 reviews

Large luxury studio with private entry, fireplace

Large new luxury studio with private entrance in a brand new house near high tech companies like Facebook, Google with Crate and Barrel furniture, Macy's Hotel Collection bedding and Samsung washer and dryer, gas fireplace, full modern kitchen and luxury appliances. We follow Airbnb’s enhanced cleaning protocol, which was developed with expert guidance.

Popular amenities for house rentals in Woodside

When is the best time to visit Woodside?

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Avg. price$387 SGD$380 SGD$393 SGD$380 SGD$399 SGD$439 SGD$465 SGD$442 SGD$398 SGD$412 SGD$408 SGD$410 SGD
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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 $90 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,820 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 of Woodside holiday 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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