
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.

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 or a quick snack at the bar-height, center island. The updated kitchen boasts modern lighting fixtures & floor-to-ceiling cabinets.

Poplar Beach Getaway - Special Pricing!
Family-friendly, relaxed home located in a quiet residential neighborhood - 1/2 block from the coastal open space, a 10-minute walk to lovely Poplar Beach, and 1/2 mile from scenic Main Street restaurants, shops and cafes. 3 bedrooms with queen beds, two baths, living area, well-equipped kitchen, spacious kid-friendly den and backyard with deck ensure that you 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.

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.

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.

Stairway to Heaven - 2 bedroom
PLEASE NOTE, we live in a 3 story home and this unit is on the lower level of our home. Also available in a 1 bedroom, this suite features a spacious living room with a fire place, flatscreen TV & a kitchenette with most everything you will need to feel at home. A nice large bedroom with a quality queen bed & linens, a large bathroom with a double sink, tub and shower. The private entrance leads to a patio with stunning views and quiet space. There is a second sunning patio do dine and rest.

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

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.

Bright home w/ atrium, BBQ & fire pit
Welcome to a thoughtfully renovated 1956 Eichler home in San Mateo - mid-century character, modern comforts, and a private backyard made for gathering. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private backyard w/ fire pit, BBQ & 8-person outdoor dining - Enclosed atrium w/ custom mural & red maple tree - Dedicated home office w/ door & fast Wi-Fi - ideal for remote work - Wood-burning fireplace & open-concept living & dining - 20 mins to SF, 15 mins to SFO & near Caltrain

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.
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

Large Home in Palo Alto, 5 bedrooms, Pool

Sunol Chalet | 80 Acres • Pool • Gym • Game Room

Luxury 4-Suite Carbon-Neutral Home With Pool

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

Private Oasis with Pool and Fire Pit

Modern Family Stay |Steps to Parks + DT Los Gatos
Weekly house rentals

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

Serene & Charming Home in Atherton border

Super Private Hidden Redwood City House and Garden

Serene Oasis in the midst of Silicon Valley

Mid-Peninsula Gem | Peloton + Hot Tub Escape

Stay Alpha Home • Luxury Modern Living

Seaside Art Gallery Loft Inspire Your Creativity

Amazing 4 BR smart home close to Stanford
Private house rentals

Beautiful Home near Stanford w/ Private Garden

Miramar Penthouse Coastal Elegance in the Heart of

Redwood Treehouse Retreat

New Cozy Home w/ A/C Near Stanford & Palo Alto

Spectacular California Ocean Front Home!

Stanford Campus Walk

New Cottage NextDoor to Stanford

Respite in the Hills! 2 bedrooms & a livingroom!
When is the best time to visit Woodside?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $552 NZD | $550 NZD | $492 NZD | $505 NZD | $531 NZD | $584 NZD | $618 NZD | $587 NZD | $529 NZD | $550 NZD | $528 NZD | $552 NZD |
| 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 $137 NZD per night before taxes and fees

Verified guest reviews
Over 1,850 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
50 of Woodside holiday 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!
Destinations to explore
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- Rentals with a patio Woodside
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- Moscone Center
- Stanford University
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- Golden Gate Park
- Oracle Park
- Muir Woods National Monument
- Capitola Beach
- Golden Gate Bridge
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- Winchester Mystery House





