
House vacation rentals in Woodside
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Top-rated house rentals in Woodside
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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.

Newly renovated 2BR/1BA in East Palo Alto
2 bd 1 ba entire unit sharing wall with other units(4 units in the house). Not suitable for people who are too sensitive to privacy . located in city of East Palo Alto ( not part of Palo Alto) , working class neighbor. read” neighborhood ”first. Don’t book if uncomfortable with working class. Only 1 parking spot available, not suitable for guests have 2 cars due to busy street Big floor mirror in 1 bedroom. be caucious if have kids . No oven in the kitchen No party and loud groups allowed

Pool, Hot tub, Sauna I Your Silicon Valley Luxury
Upscale Los Altos Hills. Peaceful and spacious 1,500 sq. ft. retreat. Ideal for business travelers, couples, nature lovers. Adjacent to 3,988-acre Rancho San Antonio Preserve with direct trail access, wildlife, serenity. Inside: workspace with fiber-optic Wi-Fi, fireplace, sauna, pool table, fully equipped kitchen and plush queen bed with guest praised mattress. Outside: exclusive access to saline heated pool and hot tub, patio with BBQ. Minutes from Stanford, Palo Alto, and top tech campuses.

Huge Suite w/ own bathroom, patio, dining, office
Forget your worries in this spacious & serene space. Large Private Suite w/ office zone, dining table, private patio w/ furniture, indoor & outdoor showers & dining, large walk-in closet. Super fast & reliable wifi. Vaulted ceilings, skylights, ceiling fans, & beautiful artwork. The suite located at back of a spacious home shared w/ 2 other suites. Walkable distance to large shopping center. Centrally located close to Stanford U & Hospital, Tech Companies & Freeways to entire Bay Area

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

Newly Remodeled Modern Home
Have fun with the whole family at this stylish place. Newly remodeled stylish home in a convenient location. Close to Stanford, downtown Palo Alto, Meta and Google etc. Parking provided with the property. Full size kitchen with brand new range. Each bedroom has a queen size bed. Extra portable bed or air bed can be added in the living room with extra $30/person per night and early notification. Large private yard great for a family to relax and enjoy the outdoor.

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.

Beach Cottage Near Coastal Trail & Ritz
This charming coastal getaway is just a 5-minute stroll to the ocean, nestled beside wide open spaces with lush southern views. The 2-bed, 2-bath home with a den comfortably sleeps five. Wake up to falcons soaring, hummingbirds buzzing around the bottlebrush blooms, and the sound of waves crashing beyond the bluffs. Your pup will love the fully fenced yard, perfect for play and relaxation. A peaceful retreat in a stunning location — rarely available.

Peaceful 3BR retreat w/ atrium & BBQ
Welcome to your peaceful Bay Area retreat in San Mateo’s Highlands – where mid-century charm meets comfort & space: - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Enclosed atrium & private fenced backyard - Fire pit, BBQ & outdoor dining area - Indoor fireplace & air conditioning - Full kitchen & dining space - Dedicated workspace w/ fast Wi-Fi - Family-friendly, single-level home w/ free parking

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. FAST WIFI. CLOSE TO 280 AND 101. We will consider pets (additional cleaning fee applies).
Popular amenities for Woodside house rentals
House rentals with a pool

Summer-house/OASIS on quiet street in ROCKRIDGE!

Beautiful Large 4BR Home with POOL

Little Poolside House near Downtown Mountain View!

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

Waterfront home w/ private dock and pool

Chic & Fun Mid-Century Modern sleeps 8 (pool)

Beautiful 3BD Home w/ Heated Pool and Fire Pit

Nuby's Bed & Breakfast (SCC Permit #251085)
Weekly house rentals

Beautiful Home near Stanford w/ Private Garden

Beautiful Cottage next to Stanford & Sand Hill Rd

Super Private Hidden Redwood City House and Garden

Redwood Treehouse Retreat

Poplar Beach Getaway - Special Pricing!

Cozy 2 Bedroom Home, Dog Friendly, w/Private Yard

Papillon ~ Renovated Home in Downtown San Carlos

1BR/1BA Duplex (C) near Castro/Caltrain Mtn View
Private house rentals

Serene & Charming Home in Atherton border

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

Serene & Peaceful Getaway in Redwood City

San Mateo Happy Haven Home w Patio/Projector

Peaceful & Cozy Home in Tech Hub

Peaceful Menlo Park House: Two bedrooms + Sunroom

Peaceful Redwood Retreat by the Coast

Cozy 2 Bedroom with Large Deck
When is the best time to visit Woodside?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,102 | ﺩ.ﺇ1,083 | ﺩ.ﺇ1,120 | ﺩ.ﺇ1,083 | ﺩ.ﺇ1,138 | ﺩ.ﺇ1,252 | ﺩ.ﺇ1,462 | ﺩ.ﺇ1,340 | ﺩ.ﺇ1,219 | ﺩ.ﺇ1,175 | ﺩ.ﺇ1,164 | ﺩ.ﺇ1,168 |
| 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 vacation rentals
Explore 50 vacation rentals in Woodside

Nightly prices starting at
Woodside vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

Verified guest reviews
Over 1,730 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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