House vacation rentals in Woodside

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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 ﺩ.ﺇ 294 per night before taxes and fees

  • Verified guest reviews

    Over 1,850 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Woodside vacation rentals include wi-fi 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!

Top-rated house rentals in Woodside

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

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Top guest favorite
Home in Half Moon Bay
4.91 out of 5 average rating, 406 reviews

Poplar Beach Getaway: Family-Friendly, Near Beach!

Family-friendly, relaxed home in a quiet residential neighborhood - 1/2 block from the blufftops, a 10-minute stroll to lovely Poplar Beach, and 1/2 mile from scenic Main Street restaurants, shops, and cafes. 3 bedrooms with queen beds, two baths, a living area, a well-equipped kitchen, a spacious kid-friendly den, and a backyard with a new deck ensure you all have room to spread out and relax after a fun day at the beach or exploring the area. Short drive to San Francisco, Santa Cruz, San Jose.

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
4.92 out of 5 average rating, 176 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 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 Palo Alto
4.95 out of 5 average rating, 272 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 Redwood City
4.95 out of 5 average rating, 116 reviews

Cozy & Fully Equipped Studio

Welcome to your perfect retreat! Our studio is fully equipped, modern, and super comfortable, offering all the amenities for an unforgettable stay. Whether you’re traveling for business or leisure, this space provides the ideal balance between comfort and convenience. 🛋 Cozy living area: Beautifully decorated with a comfortable sofa, TV 🍽 Fully equipped kitchen 🌿 Private patio: A perfect outdoor space to relax and enjoy fresh air. 🚗 Private parking with independent entrance self check in

Top guest favorite
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, 441 reviews

Luxury Silicon Valley Wellness and Work Oasis

Ideal for guests attending matches at Levi’s Stadium, business travelers, couples, and nature lovers, while staying in a quiet residential setting. Peaceful upscale exclusive use 1,500 sq ft Los Altos Hills retreat beside Rancho San Antonio Preserve. Private trail access. Fast fiber Wi-Fi, workspace, fireplace, sauna, pool table, full kitchen, plush queen bed. Year-round hot tub, BBQ patio, saline pool. Minutes to Stanford, Los Altos, Palo Alto, and major tech campuses, dining and shops.

Guest favorite
The exterior of the property is showcased, highlighting its unique architectural design with wooden paneling and large windows. A staircase leads to the entrance, and lush greenery is visible in the background, enhancing the coastal setting.
Home in Half Moon Bay
4.95 out of 5 average rating, 159 reviews

Luxury Ocean Front & Harbor View Home

Nestled in the quaint fishing village of Princeton by the Sea, just a mile north of Half Moon Bay, this stunning property is the perfect destination for your next coastal retreat. The two-bedroom, three-bathroom beautiful space sleeps up to 6 people and features spectacular views of Pillar Point Harbor and Half Moon Bay throughout the common areas and bedrooms. This is the ultimate in coastal luxury, featuring modern appliances and an open floor plan through all the common areas.

Top guest favorite
A private backyard scene features a wooden deck with a circular table and an outdoor sofa amid lush greenery. Tall grasses sway gently in the breeze, while nearby trees provide a natural backdrop under a clear blue sky.
Home in San Mateo
4.95 out of 5 average rating, 148 reviews

Mid-century retreat - fire pit and backyard

Welcome to a beautifully renovated 1956 Eichler home in the San Mateo Highlands - a distinctive mid-century space with soaring ceilings, natural light, and a private backyard made for gathering. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private backyard w/ fire pit, BBQ & outdoor dining - Enclosed atrium w/ custom mural & red maple tree - Dedicated private office w/ door - Wood-burning fireplace & full kitchen w/ gas stove - 20 mins to SF | 15 mins to SFO | Near Caltrain

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, 311 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 favorite
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 Redwood City
4.91 out of 5 average rating, 260 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
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, 145 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).

Guest favorite
The exterior view of the two-story house showcases a stucco façade with a tiled roof and a balcony overhanging the entrance. The two-car garage features double doors, while tall trees and a manicured lawn frame the property, enhancing its curb appeal.
Home in West Menlo Park
4.89 out of 5 average rating, 253 reviews

West Menlo Park Luxurious Executive Home 4050sqft

Step into this beautiful marble and hardwood floor two story 4050 sqft 5bedroom 4 bath executive large house and immediately the open concept welcomes you. The living room features large beautiful fireplace that's the focal point of one wall. The room's wood floors flow in the dining and huge gourmet kitchen area where you can enjoy a sit-down meal at the nook table. The updated kitchen boasts modern lighting fixtures & floor-to-ceiling cabinets.

Top guest favorite
Home in San Mateo
4.89 out of 5 average rating, 143 reviews

SFO 10 Min • Family 2BR + Patio Games • Baby-Ready

Two queen bedrooms, a private patio with lawn games, an in-unit washer/dryer, and a baby-and-toddler setup that covers everything from crib to high chair — this is the Bay Area family home you've been searching for. Ten minutes from SFO, a block from groceries and restaurants, and a short walk to Seal Point Park's waterfront trails, it's the kind of place where you actually unpack and settle in, not just sleep between activities

Popular amenities for Woodside house rentals

When is the best time to visit Woodside?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 1,183ﺩ.ﺇ 1,179ﺩ.ﺇ 1,054ﺩ.ﺇ 1,083ﺩ.ﺇ 1,138ﺩ.ﺇ 1,252ﺩ.ﺇ 1,326ﺩ.ﺇ 1,260ﺩ.ﺇ 1,135ﺩ.ﺇ 1,179ﺩ.ﺇ 1,131ﺩ.ﺇ 1,183
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