
House holiday rentals in Woodside
Find and book unique houses on Airbnb
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 $102 SGD 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 & 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!
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.

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 - 1 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 2 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.

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).

Extraordinary Ocean Views from Modern Abode
Tranquility awaits in our ocean view home. Enjoy beautiful ocean and mountain views from the living room, deck, kitchen and primary bedroom of this new, modern home. The beach is a brief 2-block walk away. Watch the surf and hear the soothing ocean waves from the deck and from the interior. Hardwood floors throughout the home are warm and inviting, enhanced by the maple quilted or birdseye veneer walls. A modern gas fireplace adds that extra touch of coziness.

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.

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.

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!

Delightful Stay
The whole group will enjoy easy access to everything from this centrally located home. This home has been remodeled and has everything you need from washer/dryer needs to high speed internet with home office area. Located within walking distance to the vibrant downtown of Redwood City, this home will leave you delighted. Please note: the property sits near the train tracks, most guests don’t mind.
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!

Lake Chabot Villa | Private • Pool+Spa • Game Room

Country Club Living on Golf Course & amazing views

Private Oasis with Pool and Fire Pit

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

Miramar Penthouse Coastal Elegance in the Heart of

Serene & Charming Home in Atherton border

Charming 2BR in Palo Alto

Poplar Beach Getaway - Special Pricing!

Stay Alpha Home • Luxury Modern Living

NEW! Woodside Retreat: Gorgeous Views & Hot Tub

Ocean Beach Lux Retreat Back from Remodel

Respite in the Hills! 2 bedrooms & a livingroom!
Private house rentals

Super Private Hidden Redwood City House and Garden

Stanford Retreat 4BR Jacuzzi BBQ

Spectacular California Ocean Front Home!

Cozy private home w/ A/C Palo Alto& near Stanford

Monte Sereno Cottage

Eagle Hill Craftsman

New Cottage NextDoor to Stanford

Peaceful Menlo Park House: Two bedrooms + Sunroom
When is the best time to visit Woodside?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $383 SGD | $376 SGD | $389 SGD | $376 SGD | $396 SGD | $435 SGD | $461 SGD | $438 SGD | $394 SGD | $410 SGD | $393 SGD | $411 SGD |
| 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 |
Destinations to explore
- Northern California Holiday rentals
- San Francisco Bay Area Holiday rentals
- San Francisco Holiday rentals
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- Central California Holiday rentals
- San Francisco Peninsula Holiday rentals
- San Jose Holiday rentals
- Silicon Valley Holiday rentals
- North Coast Holiday rentals
- Santa Barbara Holiday rentals
- Wine Country Holiday rentals
- Oakland Holiday rentals
- Pet-friendly rentals Woodside
- Rentals with a hot tub Woodside
- Rentals with a fireplace Woodside
- Rentals with pools Woodside
- Family-friendly rentals Woodside
- Guest house rentals Woodside
- Rentals with a patio Woodside
- Private suite rentals Woodside
- Cottage rentals Woodside
- Rentals with outdoor seating Woodside
- Rentals with a washing machine and dryer Woodside
- House rentals San Mateo County
- House rentals California
- House rentals United States
- Moscone Center
- Stanford University
- Santa Cruz Beach
- Golden Gate Park
- Oracle Park
- Muir Woods National Monument
- Capitola Beach
- Golden Gate Bridge
- Rio Del Mar Beach
- SAP Center
- Santa Cruz Beach Boardwalk
- Pier 39
- Mission Dolores Park
- Henry Cowell Redwoods State Park
- Seacliff State Beach
- Twin Peaks
- University of California-Berkeley
- Six Flags Discovery Kingdom
- Rodeo Beach
- Palace of Fine Arts
- Levi's Stadium
- Winchester Mystery House
- Montara Beach
- Bolinas Beach




