
Holiday rentals with a pool in Woodside
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Woodside
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Woodside rentals with a pool
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!

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.

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.
Condo rentals with a pool

Lakeside Retreat (w/ private parking)
Very responsive and helpful host… would definitely go back and stay there when visiting the Bay Area again

Charming 1 bedroom, 1 bath, 2 Story Condo.
Everything was great! The unit had everything you could possibly need for a trip (stocked bathroom, stocked kitchen, tons of extra towels and blankets). The neighborhood was also very quiet, which was great because we're light sleepers. I would definitely recommend this spot and would stay again.

Downtown Modern Living Condo!
It was a quiet complex and the house was a great option for us for a couple nights. Would stay again.

Luxury loft by the water
As a solo female traveler in town for business, this place was great. Short distance to the office but had everything you needed for working remote. Loved the kitchen set up and had everything I needed to make breakfast and dinner. The bed was so comfortable, I didn’t want to leave! My rav4 fit well in the garage. The walking path outside was great for either starting your day or winding down.

Art Deco Mission Flat
Lyssette’s lovely flat was exactly as described & very comfortable. It is in the heart of the mission district with so many restaurants & neat shops nearby. Highly recommended!

Cozy condo by the lake
The accommodations were nice and the area was quiet. It was a short walk to shops, restaurants, a movie theater and a 5 minute drive to a supermarket. It was a short walk to the lake which had a circumferential walking path. We particularly liked the locked parking garage. We will definitely come back.

Spacious Top Floor Condo Retreat
During my stay at Joann’s place, I felt safe and very comfortable. The whole home is bright and spotlessly clean, with greenery visible outside the windows. Parking was very convenient, and communication with her was smooth throughout. The kitchen was fully equipped, allowing me to cook and enjoy a good glass of red wine. The sofa was cozy and the bed was spacious. I was pleasantly surprised to find such a wonderful place—thank you!

The Alpaca House
Great spot for our daughter’s graduation. Having the pool was a plus.
Quick stats about holiday rentals with a pool in Woodside
Total rentals
20 properties
Total number of reviews
920 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
20 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
Destinations to explore
- San Jose Holiday rentals
- Silicon Valley Holiday rentals
- North Coast Holiday rentals
- San Joaquin River Holiday rentals
- Oakland Holiday rentals
- Sacramento Holiday rentals
- San Francisco Peninsula Holiday rentals
- Central California Holiday rentals
- San Francisco Holiday rentals
- San Francisco Bay Area Holiday rentals
- Northern California Holiday rentals
- Gold Country Holiday rentals
- Cottage rentals Woodside
- Rentals with a hot tub Woodside
- Pet-friendly rentals Woodside
- Rentals with outdoor seating Woodside
- Guesthouse rentals Woodside
- Family-friendly rentals Woodside
- Rentals with a patio Woodside
- House rentals Woodside
- Private suite rentals Woodside
- Rentals with a washing machine and dryer Woodside
- Cabin rentals Woodside
- Rentals with a fireplace Woodside
- Rentals with pools San Mateo County
- Rentals with pools California
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- 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