
Vacation rentals with a pool in Kenwood
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Kenwood
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Popular amenities for Kenwood rentals with a pool
House rentals with a pool

Vineyard Vista, Modern Farmhouse Cottage with Pool
This place was absolute perfection. The house is adorable, well decorated, comfortable, fabulous kitchen and comfortable beds. Plus coffee was there for us and a generous amount of cooking basics. We had 2 kids with us who loved roaming around the yard and the private location meant they could be as loud as they wanted while playing in the pool. The lounge chairs on the deck were perfect spot for morning coffee, afternoon cocktails and nighttime tea before bed. There were a few cuddly blankets that were great for the chilly mornings. The neighboring cows were talkative and there were a few roosters nearby and some coyotes at night - it felt like we were really in the country but also so close to charming Healdsburg. We are already planning our return trip!

Tropical Oasis with Pool & Hot Tub 30min to Sonoma
We came to visit family in the area and we felt that the location was close to parks, grocery stores, and restaurants. Everyone enjoyed the pool and the hot tub and the kitchen and dining area were large enough to accommodate all of us! House was clean, beds were comfy, we even played the board games at the home. Host was friendly and responsive; we will definitely stay here again next time we come in town to visit family (and wineries)!

Vineyard House Pool Hot Tub by Inspired in Sonoma
What a lovely house! In particular we enjoyed the expansive and fully-fenced outdoor space with our doggos and kiddos - pictures don't really quite do it justice. The pool house worked as a separate nest for the teenagers, while adults used the two bedrooms in the main building. Location is pretty perfect, with just a 5min drive to Sonoma downtown and easy access to main roads. Our host was extremely communicative, and even helped return an item we forgot at the house promptly and without delay. Hope to visit again!

Sonoma Moon House
We cannot say enough about this place. The perfect wine-tasting weekend! Exceeded expectations all around. We will stay here again!

*Heated* Swimming Pool Retreat Near Sonoma Square
We had a great stay at this spacious and well-equipped home in Sonoma! The house had everything we needed, and the outdoor space was a definite highlight—clean, warm pool and a beautiful area to relax in. Check-in was super easy, and the door code worked without any issues. The location was perfect for our trip—we used a local driving service to take us to wineries in Napa, which worked out really well. A few small things to note: the beds weren’t the most comfortable, and one of the twin beds was pretty squeaky. We also would’ve appreciated more towels since there were four of us. The en-suite shower could use some attention—it’s older and came across a bit dingy. Overall, it was a solid stay and we’d definitely consider coming back!

Serene Wine Country Retreat with Pool & Hot Tub
I almost don't want to tell you how good this place is, so we can rent it again sometime. :-) But it's that good. We visited over spring break with our daughters, eight and 11, and had one of the most amazing stays we've ever had at an Airbnb. The home, the land, the pool, and the local area are all 100% amazing. And the sunsets. You know how you sometimes stay at Airbnb's where you feel like the hosts did the bare minimum to qualify to list it? This is *not* that place. There is everything you need and more. Thank you so much SatKartar!

Sebastopol Gem, The Birdhouse. Hottub. Pool. Views
I loved this place. It was beautifully decorated and had amazing views. The pool was an added benefit on hot days! It’s somewhat small for a group because it only has one bedroom but still worth the experience.

Large Charming Home Surrounded by a Vineyard
Our stay worked great for the 3 days of golfing. We were able to use the hot tub in the evening and the place had all the amenities we needed. Kitchen was well equipped and clean when we arrived. The house had lots of space to kick out and relax. It is defiantly a feel at home place and things are well kept. Nicole was always quick to respond to any question we had. Great host!
Condo rentals with a pool

Silverado Resort Dual Suite golf course villa
We loved our time here. The condo is a great location at the start of Silverado Trail, an easy drive to many wineries. It is also a short drive to downtown Napa. We visited for a wedding and Matt was very helpful and accommodating with all our questions. We hope to stay here again next time we visit Napa!

Charming Condo: King Bed, Pool Access, 2 Patios
We had a great stay here, only about 10-15 minutes from downtown Napa and could also just stay at the site, where you could walk to a restaurant and cafe. The condo was very clean, but had everything you needed Would definitely recommend if staying in Napa

Wine Country Living at it's best at Silverado CC
Daniel was extremely proactive, helpful and responsive. We had a great time at his place, and would definitely return! Highly recommend

Casa Vina at Silverado Resort and Spa | Fireplace
I just had an amazing experience staying in Craig’s beautiful place (Unit 240). After a long ride over, I was happily greeted by a super clean, beautifully decorated place with high end towels and linens. Oh! and a nice array of sweets. I loved that the sun shined on both sides of the Unit and it has a little patio with chairs and table to sit and watch the world go by. Craig over communicated with me which I appreciated, even checking in with me during my stay to make sure everything was going well and to see if there was anything I needed. Silverado is a large property and this Unit is near everything. A 3-5 minute walk to: the Mansion where there’s a bar that has a mountainous view and overlooks one of the golf courses, The Grill restaurant where they serve all day, a Pro Shop, a little market with coffee, pastries, sandwiches, sundries and the swimming pool. Full service spa, gym tennis courts, bocce, pickleball are just across the street. I will definitely be back!

Fairways Silverado Golf and Country
I’m so glad to have found this airbnb! It was in a quiet, beautiful neighborhood. The place was cozy, clean and had everything we needed for a comfortable stay. We did have issues with wifi connections and would get bad signal on/off, also had trouble with opening the door (several tries with the code and being able to push open the door), but other than that, everything was perfect! Highly recommend this place and Kristina was awesome! I definitely would book here again if the need arises!

One Bedroom Cottage Along the Napa River
We really enjoyed our staying here. Our unit was perfect; it was crisp, clean and quiet and had everything we needed. The staff was very friendly and helpful. We were right on the Napa River Walk, which we took every morning, not to mention really close to downtown Napa. We also used the pool, which was awesome. Thanks to everyone at Riverpoint.

1 bed | 1 bath | Silverado Resort Experience
My husband and I traveled to Napa to enjoy our honeymoon and Steffanie’s place was incredible! From the easy check in process throughout our whole stay, she was the best host. We really enjoyed the location and how peaceful it was. The whole unit was filled with everything we needed to make our trip enjoyable and smooth. We will definitely be back and would book through Steffanie again!

Elegant Napa Escape
The absolute perfect choice for our stay in Napa! The condo was clean, quiet and so comfortable. Debbie went above and beyond with her suggestions, communication throughout and even stocked the fridge with many breakfast goodies for us - an unexpected surprise!
Quick stats about vacation rentals with a pool in Kenwood
Total rentals
30 properties
Nightly prices starting at
G$27,181 GYD before taxes and fees
Total number of reviews
870 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Lake Berryessa
- Golden Gate Park
- Oracle Park
- Twin Peaks
- Jenner Beach
- Bolinas Beach
- Muir Woods National Monument
- Rodeo Beach
- Clam Beach
- Mission Dolores Park
- China Beach, San Francisco
- Black Sands Beach
- Joaquin Miller Park
- Golden Gate Bridge
- Children’S Fairyland
- Drakes Beach
- Limantour Beach
- Pier 39
- Six Flags Discovery Kingdom
- San Francisco Zoo
- Painted Ladies
- Point Reyes National Seashore
- Schoolhouse Beach
- Chandon