
House holiday rentals in Woodside
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Top-rated house rentals in Woodside
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Popular amenities for Woodside house rentals
House rentals with a pool

Summer-house/OASIS on quiet street in ROCKRIDGE!
Very homey and welcoming. Family enjoyed celebrating time together in all spaces of the house, especially the back patio where our young child made believe on the well-designed pirate ship. Friendly, kind host. We walked to adorable Rockridge and BART many times. Highly recommended.

Beautiful Large 4BR Home with POOL
This spacious home was absolutely beautiful for our stay! We especially appreciated the amenities that the home provided. Specifically, the pool and vast dining spaces were a perfect match for our large family. The location was in a quiet neighborhood, central to the attractions we wanted to see including downtown San Fransisco and the Winchester house. The homeowner was great with communication throughout the booking and check in/out process. Overall, we had a lovely stay in this gorgeous home.

Large Home in Palo Alto w/Pool
Very professional, courteous and excellent communication. The location and the accommodation excellent. The hosts also allowed us to check in very late and send us lots of good information around the areas.

Little Poolside House near Downtown Mountain View!
Staying at this small house with pool was just what I needed. Enjoyed all aspects of my stay!

Mission style, w. Pool, Hot tub, walk to downtown
We stayed at Sara's while visiting family nearby, but her home felt like a vacation in itself. The backyard is magical - we spent a fair amount of time there, swimming, grilling/dining, reading/napping. The backyard (and its myriad diversions) even lured our tech-obsessed teenagers away from their devices for extended periods. Everything was well maintained, no detail overlooked. We also enjoyed the access to a peloton bike and workout equipment. The interior was clean, organized, stylish but comfortable. The sunroom and small courtyard off of the bedrooms were great for yoga or stealing a quiet moment with a cup of coffee or book. Sara was responsive and attentive. Instruction booklet was clear and helpful. The stay exceeded our expectations. We hope to be back.

Cactus House & Suite: 4 bedroom 3 bathroom
Had an excellent stay with our family. Will is one of the best airbnb hosts we have ever had and would stay again at this home or any other home he hosts without hesitation. The cactus home is luxurious and has amazing amenities like heated bathroom floors, great outdoor space with pool and hot tub, and a well equipped kitchen.

The Happy Hideaway - Pool, enjoyable backyard!
We loved the place, it had everything needed for a comfortable stay. Mei was very attentive and quick to respond to any question we had. I highly recommend it.

The Hacienda- Santa Cruz Mountain Ridgetop Retreat
We live down in Santa Cruz and wanted to treat ourselves to a poolside weekend in the mountains (and this place did not disappoint!!). Would certainly stay again and appreciate how communicative the hosts were. As we get into summer we should have known better and brought our citronella candles because the mosquitos were out with a vengeance and forced us inside- so we recommend prepping for bugs if you want to stay poolside for sunset.
Weekly house rentals

12-Min From SFO, Tastefully Designed, Work Station
Perfect place for our business trip.

Ocean Front Beach Cottage with Hot Tub & Fireplace
An ideal relaxing place right by a beach oasis. Sigward was really thoughtful about our stay and overall experience. Will definitely come back and would recommend to anyone.

Charming Home nearby Airport/San Jose Downtown/SAP
Very beautiful place, just like Quinn describe, clean & convenient, thank you for serving us ❤️

NEW! Woodside Retreat: Gorgeous Views & Hot Tub
Had a wonderful celebratory stay at this magnificent home with it’s breathtaking views, wonderful hot tub, specious and comfortable design and well equipped kitchen - it all made our stay perfect and memorable. Thank you.

Cozy 2 Bedroom Home, Dog Friendly, w/Private Yard
We had a very good time at Mel's place. The place was as per the listing. It's very close to the beach trails and also close to SF and SFO. Mel was very helpful, always replying back in minutes and answering our queries. Recommend her place for anyone looking to spend a nice peaceful weekend.

Palo Alto Modern Retreat
This is a beautiful home nestled in the heart of Palo Alto suburbs - located close to the town and university. A wonderful new constructed modern home with all the amenities of a high end home. The hosts are simply perfect and we had a wonderful 3 nights with our family and lived ones. Loved the triple glass open doors to the sanctuary back yard and fire pit in cool nights. A winner pick!

2 bedrooms house with sauna
Peter's Airbnb was even more beautiful in person than on the listing! It has a very relaxing, cozy, and calming atmosphere with beautiful decorations. There are trails to walk around on the property that have beautiful views and beautiful plants. I had this Airbnb for a work-trip for only 3 nights, but wished I could've stayed much longer!

The Artists' Tree House
Really great location in the red woods. Perfect place to spend a quiet weekend. The kitchen was well equipped. The fridge had a whole entertainment component built in so it was nice to use to play music in the kitchen. The outdoor space is super private and the hot tub is so peaceful. Bathroom is nice. Shower is spacious. Comfortable sleeping options. Overall a clearly well loved and taken care of space.
Private house rentals

Immaculate Home near Stanford w/ Beautiful Garden
Everything about our stay here has been lovely! As someone recovering from surgery, I couldn’t have found the more ideal place to recover. The main bedroom has blackout shades, and the connecting shower has an easily accesible walk in shower. The living room has an incredible entertainment system and a beautiful panaormic backyard view. It was so peaceful seeing all the critters come and go. The kitchen is also plentiful with dishes/utensils, and the dishwasher makes cleanup easy. Thank you for hosting us!

M&J cozy/sweet home/Redwood City|209
The location was perfect for our needs and the tree lined beautiful street was a nice bonus. I liked this home. Outside yard was well kept and pristine. Driveway held two cards. Spotlessly kept and comfortable tasteful furniture. Good beds. Very straightforward useful layout.

Canyon Oak House: Private, tranquil with trees
Our stay at Petra's house was truly delightful. She was a gracious and responsive host, and her clean, cozy home, nestled in a beautiful San Carlos neighborhood, provided everything we could have wished for.

Serene & Charming Home in Atherton border
This place was awesome, we did know the area and it was perfect regarding location to friends and events we needed to be at. Yes we did research to find such a place, and this was it...given the location and area the fee was extremely favorable given the location of the home.

Super Private Hidden Redwood City House and Garden
A hidden gem with warmth and character, close to everything and very private at the same time. The patio and gardens under the giant redwood is filled with fig trees, tropical ferns, orchids and banana trees. Beautiful tile and stone work decorates the paths , columns and interior spaces of this charming California Bungalow. The stuccoed interior has tall ceilings and massive beams. Big barbecue and well stocked and organized kitchen

2 Bedroom House Near Palo Alto
A beautiful house on a quiet and shady street. Half a block from a great coffee shop, and an easy walk to downtown Palo Alto. Would definitely stay again!

Redwood Treehouse Retreat
We loved our stay! The location was ideal for us, just a few minutes from a beautiful redwoods park and a short drive to the coast. This part of California is tucked away from the busy crowds of the Bay Area and feels remote. The Loma Mar outpost offers basic provisions and a restaurant a few minutes from the house, and Pescadero has a strip of shops and restaurants about ten minutes away. The house is lovely and comfortable, very peaceful.

Lantern Upper House
Very quiet and great location. Easy access to major destinations in Silicon Valley. Extremely walkable to a Whole food Store and a lot of nice restaurants. Very friendly, responsive and quiet hosts! I give a Five Stars without any reservation.
Quick stats about house rentals in Woodside
Total rentals
50 properties
Total number of reviews
1.4K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wi-Fi availability
50 properties include access to Wi-Fi
Destinations to explore
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- Santa Cruz Beach
- Capitola Beach
- Rio Del Mar Beach
- Golden Gate Park
- Stanford University
- Oracle Park
- Seacliff State Beach
- Twin Peaks
- Bolinas Beach
- Davenport Beach
- Montara State Beach
- Pescadero State Beach
- Twin Lakes State Beach
- Capitola State Beach
- New Brighton State Beach
- Muir Woods National Monument
- Rodeo Beach
- Mission Dolores Park
- China Beach, San Francisco
- Rockaway Beach
- Bonny Doon Beach
- Sumner Beach
- Black Sands Beach
- Joaquin Miller Park