
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.

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 )

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.

The most desirable & beautiful guesthouse
Centrally located modern guesthouse in Santa Clara. About 10 min drive to Apple Park, Nvidia HQ, Lawrence Caltrain Station, 49ers Levis stadium, Santa Clara Convention Center, Valley Fair Mall/Santana Row, SAP Center/Downtown SJ, SJ Mineta Airport. Your suite will have its own big gourmet Kitchen, specious full bathroom, queen bed with spacious walk in closet, Wi-Fi, TV, desk, and backyard with an outdoor seating area. There is also a shared washer and dryer in the back of the house.

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

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).

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.

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).

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.

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.

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!

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

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 house rentals in Woodside
House rentals with a pool

Beautiful Large 4BR Home with POOL

Large Home in Palo Alto, 5 bedrooms, Pool

Trailside Home, Panoramic Views

Little Poolside House near Downtown Mountain View!

Silicon Valley Executive home in Santa Clara

Mission style, w. Pool, Hot tub, walk to downtown

Luxury 4-Suite Carbon-Neutral Home With Pool

Luxury Silicon Valley Wellness and Work Oasis
Weekly house rentals

Beautiful Home near Stanford w/ Private Garden

Miramar Penthouse Coastal Elegance in the Heart of

Serene & Charming Home in Atherton border

Super Private Hidden Redwood City House and Garden

Stafford Place

NEW! Woodside Retreat: Gorgeous Views & Hot Tub

Cabo San Pedro - penthouse - Stunning Ocean Views

Cosy private place in midtown San Jose
Private house rentals

Brand New Executive Home

Redwood Treehouse Retreat

Lantern Upper House

Stanford Campus Walk

New- Stunning Oceanfront "Pelican Bluffs"

Respite in the Hills! 2 bedrooms & a livingroom!

Cozy 2 Bedroom with Large Deck

Amazing 4 BR smart home close to Stanford
When is the best time to visit Woodside?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £224 | £220 | £228 | £220 | £231 | £254 | £269 | £256 | £230 | £239 | £230 | £240 |
| Avg. temp | 10°C | 12°C | 13°C | 15°C | 17°C | 19°C | 20°C | 20°C | 20°C | 18°C | 13°C | 10°C |
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 £52 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!
Destinations to explore
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- Family-friendly rentals Woodside
- Rentals with a hot tub Woodside
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- House rentals San Mateo County
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- Moscone Center
- Stanford University
- Santa Cruz Beach
- Golden Gate Park
- Capitola Beach
- Muir Woods National Monument
- Oracle Park
- Golden Gate Bridge
- Rio Del Mar Beach
- Seacliff State Beach
- SAP Center
- Mission Dolores Park
- Santa Cruz Beach Boardwalk
- Twin Peaks
- Pier 39
- Henry Cowell Redwoods State Park
- University of California-Berkeley
- Six Flags Discovery Kingdom
- Montara Beach
- Palace of Fine Arts
- Levi’s Stadium
- Winchester Mystery House
- Bolinas Beach
- California’S Great America




