Kenwood Vacation Rentals

Compare 616 vacation rentals with savings up to 30% off this summer.
USA > California > Kenwood

Make Kenwood your next getaway


Explore Kenwood house rentals, cottages, estate rentals, and more


House rentals

View 7 House rentals


View 2 Cottages

Estate rentals

View 2 Estate rentals

Kenwood vacation rentals for every getaway

Dog-friendly Hot tub Internet
Casa de Azel
2 Bed | 2 Bath | Sleeps 4

Casa de Azel - Kenwood, CA

$463 avg / night
Sonoma Pool Retreat
3 Bed | 4 Bath | Sleeps 8

Sonoma Pool Retreat - Kenwood, CA

$1,220 avg / night
Kenwood Retreat
3 Bed | 2 Bath | Sleeps 8

Kenwood Retreat - Kenwood, CA

$561 avg / night
Wine Country Farmhouse
4 Bed | 2.5 Bath | Sleeps 8

Wine Country Farmhouse - Kenwood, CA

$1,009 avg / night
Tuscany in Sonoma
3 Bed | 3.5 Bath | Sleeps 6

Tuscany in Sonoma - Kenwood, CA

$1,769 avg / night

View 7 more homes

Recent Kenwood vacation rental reviews

If you are looking for a well appointed Sonoma meets Tuscany style space, this home is perfect. You are not just renting a house, you are renting a whole estate style property with a hundred instagram worthy spaces. The pool area has not only a large pool and outdoor dining space, but adorable swing cabanas, bacci court, lounge chairs, shaded bar top tables. There is an additional outdoor dining area closer to the house with a fire pit and more lounging spaces. There are lemon and orange trees in a small grove on one side of the house. We made lemonade. There is a chicken coop that enthralled our kids and the hillside surrounding the house is an actual vineyard. There's an old stone barn with plank doors that's covered in ivy. The house has every possible cooking, baking and entertaining necessity we required (plus stuff we didn't need, but loved): cast iron pots and pans, ample wine glasses, beautiful serving dishes, gas stove, pizza oven, two dishwashers. The bathrooms are styled old world, but large and spacious with modern showers and elegant wash basins. There mattresses and linens are the same quality as the ones in your own home. The furniture and textiles are rich, comfortable and well made.
Laen G. | May 2023
Our stay at this beautiful home was absolutely perfect. The spaces for entertainment and for sleeping were spot on for our party of 7.
Sherrie B. | May 2023
Truly great stay here. Very clean and well maintained/stocked. Rooms were all huge & with great bathrooms. Fireplace was used every day which was nice touch. Close to all the wineries we wanted to see, no more than 25 min from Oakville Grocery if you go over the mountain!
Alyssa W. | May 2023
Kenwood Frequently Asked Questions

Yes, 10 of our Kenwood homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 49 of our Kenwood vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >

Some of the most popular amenities in our Kenwood vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Kenwood team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Kenwood, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning