
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.
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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!

Unreal Beachfront Marin Getaway!
A group of lifelong friends and I meet once a year for a long weekend to catch up, decompress, and spend time together. We chose San Francisco this year and after hunting on AirBnB we stumbled across this estate on JAR Farms. The host Nikki was proactive, helpful, and responsive. We arrived on Wednesday and drove to thru the gate into a lush oasis. The pictures on the listing didn't do the property justice. We arrived at the guest house to a welcome gift of wine, local honey, and snacks. We were a group of 6 adults and the guest house was cozy yet a perfect size for a reunion of friends. We were given a tour of the property showing us the boat house/beach, grand staircase to the bay overlook, the pool house (pool and hot tub), gardens, bee hives, and the many trails on the property. The mornings we hiked Monahan Trail at the adjacent Old St. Hillary's Preserve. In the afternoons we enjoyed the hot tub and a nice bbq dinner. Perfect weekend! HIGHLY recomended. Will be returning!

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.

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.

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 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.
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.

Luxury Penthouse ~ Best View of San Francisco
Amazing condo. There is literally no other way to see the Bay Bridge like this, it's absolutely worth the view!! There were also stocked snacks and beautiful flowers 🥰

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.

Modern 2BR Condo | Business & Long-Term Stays
This was one of the best Airbnb stays I’ve had. Tucked in a quiet, green neighborhood just minutes from downtown Palo Alto, the location was perfect. Peaceful & residential, yet incredibly convenient. Having an organic grocery store within walking distance was a big plus. The home itself is beautifully done, spotless, thoughtfully designed, & filled with everything you might need for a comfortable and relaxed stay. The kitchen was well-equipped, the bed was cozy, and the entire space had a calm, welcoming vibe that instantly put me at ease. But what truly elevated the experience was Johana. She is one of the kindest and most considerate hosts I’ve ever met, warm, responsive, and genuinely invested in making sure everything was perfect. Whether it was a quick question or a small request, she was always just a message away and incredibly thoughtful in her responses. You can tell she really cares. I would stay here again in a heartbeat & I am looking forward to it.

La Casa de Alpaca
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
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- Santa Cruz Beach
- Capitola Beach
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- Golden Gate Park
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- Oracle Park
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