
House vacation rentals in Woodside
Find and book unique houses on Airbnb
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.ﺇ 294 per night before taxes and fees

Verified guest reviews
Over 1,850 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!
Top-rated house rentals in Woodside
Guests agree: these houses are highly rated for location, cleanliness, and more.

Poplar Beach Getaway: Family-Friendly, Near Beach!
Family-friendly, relaxed home in a quiet residential neighborhood - 1/2 block from the blufftops, a 10-minute stroll to lovely Poplar Beach, and 1/2 mile from scenic Main Street restaurants, shops, and cafes. 3 bedrooms with queen beds, two baths, a living area, a well-equipped kitchen, a spacious kid-friendly den, and a backyard with a new deck ensure you all 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.

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.

Luxury Ocean Front & Harbor View Home
Nestled in the quaint fishing village of Princeton by the Sea, just a mile north of Half Moon Bay, this stunning property is the perfect destination for your next coastal retreat. The two-bedroom, three-bathroom beautiful space sleeps up to 6 people and features spectacular views of Pillar Point Harbor and Half Moon Bay throughout the common areas and bedrooms. This is the ultimate in coastal luxury, featuring modern appliances and an open floor plan through all the common areas.

Mid-century retreat - fire pit and backyard
Welcome to a beautifully renovated 1956 Eichler home in the San Mateo Highlands - a distinctive mid-century space with soaring ceilings, natural light, and a private backyard made for gathering. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private backyard w/ fire pit, BBQ & outdoor dining - Enclosed atrium w/ custom mural & red maple tree - Dedicated private office w/ door - Wood-burning fireplace & full kitchen w/ gas stove - 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).

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. The updated kitchen boasts modern lighting fixtures & floor-to-ceiling cabinets.

SFO 10 Min • Family 2BR + Patio Games • Baby-Ready
Two queen bedrooms, a private patio with lawn games, an in-unit washer/dryer, and a baby-and-toddler setup that covers everything from crib to high chair — this is the Bay Area family home you've been searching for. Ten minutes from SFO, a block from groceries and restaurants, and a short walk to Seal Point Park's waterfront trails, it's the kind of place where you actually unpack and settle in, not just sleep between activities
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

Little Poolside House near Downtown Mountain View!

Waterfront home w/ private dock and pool

Lafayette Treehouse - Relax and Rejuvenate

Private Oasis with Pool and Fire Pit

The Hacienda- Santa Cruz Mountain Ridgetop Retreat
Weekly house rentals

Captivating Muir Beach Home With Sweeping Views

Heart of Silicon Valley Studio/Cottage

Charming 1930 Spanish Haven close to everything

Tranquil private 2 BR home in Palo Alto/Stanford

Seaside Art Gallery Loft Inspire Your Creativity

Fabulous Beach Get Away - Brand New Beach House

Oceanfront Oasis, Sunsets & Crashing Waves

Lagoonfront Retreat: 3BR House Near SFO
Private house rentals

Private Cottage House - Walk to Beaches Harbor

Serene & Charming Home in Atherton border

Super Private Hidden Redwood City House and Garden

Panoramic Bay View • Single-Level • 1Gbps WiFi

New Cozy Home w/ A/C Near Stanford

Serene & Peaceful Getaway in Redwood City

Modern Vintage Garden Bungalow

Stunning Modern Home with Amazing Views of Valley
When is the best time to visit Woodside?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 1,183 | ﺩ.ﺇ 1,179 | ﺩ.ﺇ 1,054 | ﺩ.ﺇ 1,083 | ﺩ.ﺇ 1,138 | ﺩ.ﺇ 1,252 | ﺩ.ﺇ 1,326 | ﺩ.ﺇ 1,260 | ﺩ.ﺇ 1,135 | ﺩ.ﺇ 1,179 | ﺩ.ﺇ 1,131 | ﺩ.ﺇ 1,183 |
| 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
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- Rentals with a patio Woodside
- Private suite rentals Woodside
- Family-friendly rentals Woodside
- Pet-friendly rentals Woodside
- Rentals with a fireplace Woodside
- Guesthouse rentals Woodside
- Rentals with pools Woodside
- Rentals with a hot tub Woodside
- Rentals with a washer and dryer Woodside
- Rentals with outdoor seating Woodside
- House rentals San Mateo County
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- Stanford University
- Golden Gate Park
- Santa Cruz Beach
- Muir Woods National Monument
- Capitola Beach
- Oracle Park
- Golden Gate Bridge
- Santa Cruz Beach Boardwalk
- Moscone Center
- Levi's Stadium
- University of California-Berkeley
- SAP Center
- Henry Cowell Redwoods State Park
- Mission Dolores Park
- Rio Del Mar Beach
- Pier 39
- Six Flags Discovery Kingdom
- Chase Center
- Seacliff State Beach
- University of California San Francisco
- California’S Great America
- Palace of Fine Arts
- Rodeo Beach
- Montara Beach





