
House holiday rentals in Woodside
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Top-rated house rentals in Woodside
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Popular amenities for house rentals in Woodside
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
Immaculately maintained, spacious property. Very relaxing. Close to all the necessary shops. Well equipped for families.

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
Sara and Nic were gracious and very responsive hosts. Their home is spacious, clean, comfortable, and suited our needs perfectly. The outdoor space also looked wonderful but we didn't use it much because our visit was during winter.

Beautiful 3BD Home w/ Heated Pool and Fire Pit
The house was great for our family stay. Lots of space, all on one level, and beautiful outdoor space. We travelled with our kids and they had a great time in the pool :) Note there is extra cost if you want the pool to be heated. Thanks for a great stay!

Bay Area Refuge- Waterfall/Cave Spa, Amazing Views
The Treehouse was a perfect getaway for a family of 8 adults and one child. Surroundings were beautiful. Nature was plentiful. The place had great amenities, kitchen well stocked, and the pool and hot tub one of a kind of !! We all had a great stay !!!

Bay Area getaway w/ Pool + Heated Spa + EV charger
The house was awesome, having everything we needed, plus some nice extra touches like pool toys and snacks for a movie night. The only downside was that they had instructions to not turn the ac down past 72 and it was a very hot weekend, the house held onto a lot of heat and the bedrooms were very warm. The pool and spa were great, and we loved hanging out in the outdoor space.

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
Wonderful place and responsive host. Perfect for a short family trip to Bay Area!

Oceanfront Views - Steps to the Beach
My team had a wonderful time at Stefan's place! The ocean views are magical and the house is very spacious. Incredible spot about an hour away from SF and Palo Alto. Stefan was very communicative and friendly. Check-in and check-out were simple. Very clear house rules. No complaints at all! We will definitely be back.

NEW! Woodside Retreat: Gorgeous Views & Hot Tub
Great spot with amazing views. We came for a wedding at mountain terrace and it was the perfect place to stay.

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.

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!

Tranquil private 2 BR home in Palo Alto/Stanford
We had such a lovely stay here while celebrating our son’s graduation from Stanford. The home was clean, quiet, and very comfortable. It was just what we needed after busy days on campus. The location is fantastic and very close to Stanford, which made everything so easy. The little touches made it feel special. There were beautiful flowers in the yard and we saw a cute little bunny hopping around every day. It was such a peaceful and happy place to come back to. The house had everything we needed and made our time extra memorable. We would definitely stay here again.

Entire quest suite w/separate living room 1stfloor
I had such a lovely stay. The neighborhood was really nice and the home was exactly like the pictures. Everything was clean and ready to go for my stay. The bed was very comfortable and I slept well my whole trip. I would definitely stay here again in the future.

A private beachy pad in Montara
We had a great stay in Rachael’s studio and wholeheartedly recommend it to anyone looking for a cozy and private place to unwind and recharge those batteries. The listing was easy to find and check in was a breeze. The apartment itself is bright, nicely appointed and located in a beautiful residential area not far from Montara State Beach. Though we didn’t meet Rachael in person, communication with her was easy and she was always available for questions etc. We would definitely stay here again!
Private house rentals

Immaculate Home near Stanford w/ Beautiful Garden
We truly felt at home in this beautiful residence. The beds are very comfortable. The outdoor space was so nice to enjoy early morning coffee and meals, a perfect mix of sun and shade. The neighborhood is quiet and peaceful at night. Thank you for opening your home to 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

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.

San Mateo Happy Haven Home w Patio/Projector
Beautifully remodeled home. The kids loved the back yard and the neighbourhood was quiet yet safe. We loved that the kitchen had a proper gas stove and all the necessary amenities to cook a meal for a family.
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
Wifi availability
50 properties include access to wifi
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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
- Davenport Beach
- Montara State Beach
- Bolinas 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