House vacation rentals in Woodside

Find and book unique houses on Airbnb

Quick stats about house rentals in Woodside

  • Total vacation rentals

    Explore 40 vacation rentals in Woodside

  • Nightly prices starting at

    Woodside vacation rentals start at G$16,703 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,870 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

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 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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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
4.93 out of 5 average rating, 181 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
Home in Half Moon Bay
4.91 out of 5 average rating, 417 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 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, 279 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.

Superhost
The exterior of a single-family home is presented, featuring a well-manicured front yard with shrubbery and stone accents. A front path leads to the entrance, framed by large windows that illuminate the living space. A garage with multiple doors is visible on the right.
Home in Redwood City
4.84 out of 5 average rating, 99 reviews

Serene & Charming Home in Atherton border

Nestled in the border between Atherton & Redwood City CA, this exquisite property boasts privacy, tranquility, and natural beauty. With its serene surroundings, this house offers a truly idyllic retreat. The home offers a living room with large windows overseeing the front yard, a formal dining room with custom cork accent wall and French doors to the front porch. Three bedrooms, one ensuite and two serviced by a hall bath, complete the first floor, there is a recreation room above the garage.

Guest favorite
A spacious living area features a modern design with a wall-mounted TV and a sleek fireplace. A large dining table is set for gatherings, while natural light enters through windows, illuminating the open kitchen space in the background.
Home in East Palo Alto
4.92 out of 5 average rating, 232 reviews

Brand new luxury house near high tech companies

Luxury stay with a business lounge of your own. A great place for a team travelling together to share ideas around the counter or relax with the 100" fireplace and 70" TV/ROKU. 4 bedrooms and 2 bathrooms near FB, G and Stanford with top notch appliances and elegant modern design. One of the two units of a duplex. The other unit is an in-law suite with its own entrance and not included in this listing. We follow Airbnb’s enhanced cleaning protocol, which was developed with expert guidance.

Guest favorite
A modern living area features a fireplace framed by a stylish mantel. A sectional sofa in grey fabric is positioned toward a wall-mounted television. Two armchairs are placed opposite the sofa, while a coffee table sits in the center. Decorative plants and artwork add visual interest.
Home in Palo Alto
4.96 out of 5 average rating, 119 reviews

Fully Remodeled Home AC-WiFi-Stanford-Go0gle

Enjoy a stylish experience at this centrally-located place! This light-filled, mid-century modern gem is tastefully remodeled with high-end Scandinavian furniture (BoConcept sofa, carpet, wall units) and European oak floor. **Mini split AC is installed in July 2023.** It has a spacious common area for families to relax, a full kitchen, 3 queen beds, 2 bathrooms and fast WiFi (>200 Mbps). Go0gle/Stanford is a 5~10min drive and local grocery/coffee shops (Peet's) are within walking distance.

Guest favorite
The living area features a leather sofa paired with a patterned rug and a glass coffee table. A dining area is visible in the background, illuminated by natural light from large windows. Soft decorative elements, including a fluffy pouf and indoor plants, enhance the welcoming ambiance.
Home in Belmont
4.94 out of 5 average rating, 107 reviews

Sunlit 2B1B house w/ Deck & Garden on Belmont hill

Escape to this peaceful retreat with new furniture, beautiful garden and nice views over Belmont hill! Luxury like your own home: - Leather sofa & Smart TV - Complete cookware and dining essentials - Big deck with a dining set - Large Private Backyard for relaxation Convenience: - Surrounded by various attractions - San Francisco and San Jose are both half-an-hour away - Easy access to Caltrain, US 101, I-280, and SR 92 - 15-minute drive from San Francisco International Airport

Superhost
An open living area is featured, with a dining table made of wood set for meals. A comfortable couch invites relaxation, while large windows provide natural light. A wall-mounted projector displays a scenic image, adding a unique element to the room.
Home in East Palo Alto
4.9 out of 5 average rating, 119 reviews

NEW! Luxury Modern 4BR In Heart of Silicon Valley

This modern renovated house is central to everything in Silicon Valley. Great place to stay for business trips, vacations & family gateway. This home features an open floor plan, a modern chef’s kitchen, and home movie theater in the living room w/ 5 beds in 4 bedrooms. **Prime Location Downtown Palo Alto - 10 min Stanford University/Hospital - 15 min Santa Clara Conventional Center - 16 min Levi's Stadium - 20 min SJC Airport - 20 min SAP Center at SJ - 25 min SFO Airport - 25 min

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, 323 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
The enchanting exterior of a Spanish style home is highlighted by a textured yellow facade and red tiled roof. Arched doorways lead into the entrance, surrounded by vibrant greenery and blooming plants. A pathway made of patterned tiles guides towards the front door.
Home in San Carlos
4.82 out of 5 average rating, 204 reviews

Charming 1930 Spanish Haven close to everything

Enjoy a stay in the charm of 1930 Spanish style home with all the modern conveniences and comfort of today. This home is both ideal for the family visiting the bay area as well as the professional trip to the bay area. Conveniently located steps away from original restaurants and about a mile from the train station or freeways. Guests have WiFi, a fully stocked kitchen, and based on season, fruit from 17 trees including apple, lemon, pear, orange and more.

Guest favorite
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
4.95 out of 5 average rating, 168 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 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, 454 reviews

Luxury Silicon Valley Wellness and Work Oasis

Ideal for 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.

Popular amenities for Woodside house rentals

When is the best time to visit Woodside?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$67,228 GYDG$67,019 GYDG$59,920 GYDG$61,799 GYDG$59,503 GYDG$84,139 GYDG$75,370 GYDG$71,612 GYDG$64,514 GYDG$67,019 GYDG$64,305 GYDG$67,228 GYD
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