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
4.94 out of 5 average rating, 133 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 )

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, 166 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.

Guest favorite
A modern living area features a full sofa bed, a flat-screen TV, and a compact desk illuminated by a lamp. The light-colored walls are complemented by decorative curtains, and a dining table with light wood finishes is positioned in the foreground.
Home in East Palo Alto
4.98 out of 5 average rating, 102 reviews

Well Maintained, Super Clean 1B/1B guest house

** A construction is under way on the opposite side of the lot. There might be daytime noise. ** ** This listing is for the JADU on the left hand side to the main house and does not share walls with the other unit. ** Welcome to our newly converted 1B/1B JADU. All furniture was purchased after construction. We strive to keep our space simple, clean and well maintained and try our best to provide our guests a comfortable space to rest and rejuvenate. The space is best for 1 to 2 people.

Guest favorite
A wooden hot tub is positioned on a deck facing the ocean, with waves gently lapping at the shore. The sunset casts warm hues over the water, while wooden posts and ropes define the perimeter of the deck.
Home in Moss Beach
4.93 out of 5 average rating, 274 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.

Guest favorite
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
4.92 out of 5 average rating, 384 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

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, 291 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
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
4.9 out of 5 average rating, 248 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 favorite
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, 380 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.

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, 412 reviews

Luxury Silicon Valley Wellness and Work Oasis

Peaceful upscale 1,500 sq ft Los Altos Hills retreat beside Rancho San Antonio Preserve. 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 favorite
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, 143 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 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
4.91 out of 5 average rating, 102 reviews

3BR Near Stanford, Bonus Room, No Check-Out Chores

Welcome to our bright, relaxing home conveniently near Stanford. 3 BR, 2 BA, 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. Near to VMWare, Tesla, and the VA. Highway 280 is about 5 minutes.

Top guest favorite
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, 119 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.

Popular amenities for Woodside house rentals

When is the best time to visit Woodside?

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Avg. priceﺩ.ﺇ1,102ﺩ.ﺇ1,083ﺩ.ﺇ1,120ﺩ.ﺇ1,083ﺩ.ﺇ1,138ﺩ.ﺇ1,252ﺩ.ﺇ1,326ﺩ.ﺇ1,260ﺩ.ﺇ1,135ﺩ.ﺇ1,179ﺩ.ﺇ1,131ﺩ.ﺇ1,183
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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.ﺇ257 per night before taxes and fees

  • Verified guest reviews

    Over 1,820 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!

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