Kenwood holiday rentals

We found 1,211 holiday rentals — enter your dates for availability
Discover a selection of 50 homes and other holiday rentals in Kenwood that are perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include a pool and a washer and dryer. At the end of the day, you're sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Kenwood

Showing deals for:11 Dec - 18 Dec

Children’s area
Interior
Dining
Terrace/patio
Exceptional
(5 reviews)

7-Acre Farm w/ Pool Nestled in Sonoma Wine Country - 4Bds + 3 Bath

Petaluma

8% off
S$8,912
for 7 nights, 1 room
S$1,273 per night
includes taxes & fees
7-Acre Farm w/ Pool Nestled in Sonoma Wine Country - 4Bds + 3 Bath
Terrace/patio
Bedroom 9 with queen bed and shared bathroom
Living area
Exterior
Exceptional
(151 reviews)

Casa Bella Estate in Wine Country w/ New Pool!

Kenwood

7% off
S$20,382
for 7 nights, 1 home
S$2,912 per night
includes taxes & fees
Casa Bella Estate in Wine Country w/ New Pool!
Living area
Room
Exterior
Pool
Exceptional
(27 reviews)

Luxury Vineyard Creek Ranch Sonoma

Sonoma

8% off
S$16,129
for 7 nights, 1 home
S$2,304 per night
includes taxes & fees
Luxury Vineyard Creek Ranch Sonoma
Courtyard Connecting the Office and the Water Tower
Exterior
Cypress Bungalows Party Barn!
Bungalow 4 Office with Sofa Sleeper
Exceptional
(9 reviews)

The Cypress Bungalows

Sonoma

7% off
S$9,528
for 7 nights, 1 home
S$1,361 per night
includes taxes & fees
The Cypress Bungalows
Enjoy the quiet serenity  around the pool and take in the lush landscape.
Dining room.
Entry.
Living room.
Exceptional
(148 reviews)

Amazing Get-Away! Enjoy the Views! Relax on Deck or by Pool. Minutes to Plaza.

Sonoma

8% off
S$6,844
for 7 nights, 1 home
S$978 per night
includes taxes & fees
Amazing Get-Away! Enjoy the Views! Relax on Deck or by Pool. Minutes to Plaza.
Peloton bike in the master wing with cycling clips, guest supplied shoes.
Incredible views from the great room of the opposing vineyard mountains.
The splendor of your own Sonoma estate tucked within the famous Carneros region
Sunsets from the pool are a guest favorite
Exceptional
(94 reviews)

Wine country luxury including executive chef & private resort amenities + SAUNA

Sonoma

8% off
S$20,814
for 7 nights, 1 home
S$2,973 per night
includes taxes & fees
Wine country luxury including executive chef & private resort amenities + SAUNA
Private kitchen
Picnic tables & Fire Pit
Interior
Living area
Exceptional
(39 reviews)

Beautiful Gated Winemaker’s Estate 1 mi to Historic Sonoma Town Square

Sonoma

12% off
S$12,875
for 7 nights, 1 home
S$1,839 per night
includes taxes & fees
Beautiful Gated Winemaker’s Estate 1 mi to Historic Sonoma Town Square
Private kitchen
Exterior
Bar (on property)
Living area
Exceptional
(11 reviews)

Stunning Private Estate in Wine Country - Carneros

Sonoma

8% off
S$42,037
for 7 nights, 1 home
S$6,005 per night
includes taxes & fees
Stunning Private Estate in Wine Country - Carneros
Vintage farmhouse with wraparound veranda amidst gardens and trees
Enjoy an evening swim, relax in spa or play bocce under the lights!
Distinctive farmhouse with wraparound veranda set on nearly four private acres
Another view at dusk
Exceptional
(145 reviews)

Wine Country Estate: Exceptional Privacy & Location, Year-round Pool, Spa, Bocce

Kenwood

8% off
S$9,492
for 7 nights, 1 home
S$1,356 per night
includes taxes & fees
Wine Country Estate: Exceptional Privacy & Location, Year-round Pool, Spa, Bocce
Dinning Room with table sitting for 12-14 adults
Sunset from the pool.
Full Dinner sets for 15 full dinner place settings.
Dinning Room with table sitting for 12-14 adults
Exceptional
(137 reviews)

Gorgeous Vineyard Views, Large private home w/heated Pool & Hot Tub included!

Glen Ellen

16% off
S$13,498
for 7 nights, 1 home
S$1,928 per night
includes taxes & fees
Gorgeous Vineyard Views, Large private home w/heated Pool & Hot Tub included!
Outdoor spa tub
Outdoor dining
Interior
Spiral staircase leads to downstairs bedroom & bathroom
Exceptional
(274 reviews)

Modern Italian Villa with Infinity Pool & Panoramic Views

Glen Ellen

8% off
S$9,936
for 7 nights, 1 villa
S$1,419 per night
includes taxes & fees
Modern Italian Villa with Infinity Pool & Panoramic Views
Poolside firpit seating area overlooking Sonoma Valley views and epic sunsets
Propane firepit outdoor seating for 14 guests
Chef's Kitchen: Viking 8 burner duel fuel range, Nespresso & Keurig with pods
Dining room & kitchen with winery vineyard views from every room
Exceptional
(33 reviews)

Stunning Private Wine Country Estate - Epic Views - Pool - Hot Tub - Sunsets!

Sonoma

8% off
S$28,864
for 7 nights, 1 home
S$4,123 per night
includes taxes & fees
Stunning Private Wine Country Estate - Epic Views - Pool - Hot Tub - Sunsets!
10-foot outdoor dining table. 
- Built-in heaters just in case
Sun rise over the mountains
The dining table feeds out to the patio.
Huge 10' couch, chaise lounger, 1.5+ chair, gorgeous vaulted ceilings
Exceptional
(202 reviews)

Spa-like Estate, Wine Country Getaway, above the Sonoma Square, Amazing Views

Sonoma

8% off
S$11,738
for 7 nights, 1 home
S$1,677 per night
includes taxes & fees
Spa-like Estate, Wine Country Getaway, above the Sonoma Square, Amazing Views
Chat with the hot-tubers while preparing a gourmet meal
Open plan living room with sightlines to kitchen and all back yard amenities
Open plan kitchen with large island and 3  bar seats adjacent to dining area
View of the main house deck and pool from the dining table
Exceptional
(161 reviews)

Lovely Home & Cottage with Pool, Bocce and Game Room Near Sonoma Square

Sonoma

8% off
S$11,319
for 7 nights, 1 home
S$1,617 per night
includes taxes & fees
Lovely Home & Cottage with Pool, Bocce and Game Room Near Sonoma Square
Enjoy wine/cheese and meals comfortably on the large deck
So close to Sonoma, yet you feel in the middle of country
Living area
Livingroom
Exceptional
(90 reviews)

Single Story Ranch w/ Pool - 2.5 Acres close to Sonoma Square and Sonoma Raceway

Sonoma

8% off
S$8,439
for 7 nights, 1 home
S$1,206 per night
includes taxes & fees
Single Story Ranch w/ Pool - 2.5 Acres close to Sonoma Square and Sonoma Raceway
Living room.
Dining room doors open to the outside patio for indoor/outdoor living.
Dining room has wet bar, wine fridge, and ice machine.
Enjoy a beautiful sunset by the firepit.
Exceptional
(155 reviews)

Wine Country Escape: Luxury Estate, Pool, Sauna, Steam, Spa, Views, 5+ Bedrooms

Santa Rosa

8% off
S$23,062
for 7 nights, 1 home
S$3,295 per night
includes taxes & fees
Wine Country Escape: Luxury Estate, Pool, Sauna, Steam, Spa, Views, 5+ Bedrooms
Living Room and back door exit to pool area
Exterior detail
Large dining table
Interior
Exceptional
(84 reviews)

WOW! A little bit of France...in Sonoma!

Sonoma

8% off
S$8,208
for 7 nights, 1 home
S$1,173 per night
includes taxes & fees
WOW! A little bit of France...in Sonoma!
50' Pool
Outdoor dining for lunches and long summer evening for 12 people
The lavender in July is spectacular.
Private kitchen
Exceptional
(256 reviews)

Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

Kenwood

8% off
S$15,988
for 7 nights, 1 home
S$2,284 per night
includes taxes & fees
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
Enclosed porch adjoining kitchen with dining area
Great room: formal dining area,  grand piano, fireplace, tv
Property grounds
Kitchen with large central island
Exceptional
(64 reviews)

Stay at Roche Winery's Sonoma Vineyard Retreat

Sonoma

16% off
S$7,906
for 7 nights, 1 home
S$1,129 per night
includes taxes & fees
Stay at Roche Winery's Sonoma Vineyard Retreat
Exterior
Property grounds
Exterior
Interior
Exceptional
(65 reviews)

Wine Country Retreat between Sonoma & Napa Valleys

Glen Ellen

8% off
S$10,121
for 7 nights, 1 home
S$1,446 per night
includes taxes & fees
Wine Country Retreat between Sonoma & Napa Valleys
Looking out the French doors - room with a view
Property grounds
She is tucked into the corner of my ranch - two other small buildings near by
Romantic room for sure
Exceptional
(34 reviews)

Sonoma Country Cottage, On 50 Acre Ranch - Big Views, A Magical Spot.

Petaluma

8% off
S$1,619
for 7 nights, 1 cottage
S$231 per night
includes taxes & fees
Sonoma Country Cottage, On 50 Acre Ranch - Big Views, A Magical Spot.
Dining
Exterior detail
Living area
Interior
Exceptional
(68 reviews)

Beautiful Home in Northwest Napa

Napa

9% off
S$3,734
for 7 nights, 1 home
S$533 per night
includes taxes & fees
Beautiful Home in Northwest Napa
Front of house.  Parking for up to 5 cars in the driveway and garage.
Living room with XL masonry fireplace
Lounge chairs by pool
Family Room
Exceptional
(128 reviews)

1-acre Private Backyard with Large Pool

Glen Ellen

20% off
S$7,033
for 7 nights, 1 home
S$1,005 per night
includes taxes & fees
1-acre Private Backyard with Large Pool
Private kitchen
Outdoor dining
Room
Dining
Exceptional
(120 reviews)

Sonoma Wine Country Madison Escape TOT #2380N

Sonoma

8% off
S$4,121
for 7 nights, 1 home
S$589 per night
includes taxes & fees
Sonoma Wine Country Madison Escape TOT #2380N
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

The charming area of Kenwood awaits your stay

Enjoy the wineries and other features of Kenwood. Travellers especially like the spas, gardens and parks in this romantic and relaxing city. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Kenwood

Are you hoping to find top things to see and do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Kenwood a fun spot to go on holiday. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Napa Valley Wine Train (16.2 mi / 26 km)
  • Oakmont Golf Club (2.8 mi / 4.6 km)
  • Benziger Family Winery (3.8 mi / 6 km)
  • HALL St. Helena Winery (7.2 mi / 11.7 km)
  • V. Sattui Winery (7.4 mi / 11.9 km)
  • Beringer Vineyards (7.6 mi / 12.2 km)

Exploring the natural features in Kenwood

Whether you're an active traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Kenwood. These are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Jack London State Historic Park (3.9 mi / 6.3 km)
  • Spring Lake Park (6.5 mi / 10.4 km)
  • Old Courthouse Square (9.3 mi / 14.9 km)
  • Yountville Park (9.6 mi / 15.5 km)
  • French Laundry Culinary Garden (9.8 mi / 15.8 km)
  • Petrified Forest (11 mi / 17.7 km)

How to get to and around Kenwood

The nearest airport is in Santa Rosa, CA (STS-Sonoma County), located 15.5 mi (25 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Oakland, CA (OAK-Oakland Intl.), which is 51.7 mi (83.2 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Kenwood?
The most popular types of holiday rentals in Kenwood are houses. Hoping for something different? Vrbo offers a variety of options to match our guests' requirements, so you'll see holiday homes in loads of shapes and sizes. The perfect fit is ready and waiting for you — lock in yours today.
How much does it cost to rent a holiday rental in Kenwood?
A range of factors can affect how much you'll pay for a holiday rental in Kenwood, such as the season, type of property and length of stay. But, all our holiday homes have something in common — exceptional value. Simply enter your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Kenwood?
Prices for beach houses in Kenwood may differ depending on the style and size of the property and time of year you're travelling. All you need to do is enter your travel dates into Vrbo and the number of guests to view your rental options and prices. From there you can use our filter tool to narrow your search by amenities, ratings, nearby activities and more.
Are there pet-friendly holiday rentals in Kenwood?
There are, yes. You'll find 73 stays that welcome pets in Kenwood on Vrbo. Our furry best friends deserve a getaway too, so simply use our search function for pet-friendly holiday rentals to find a pad where Fido can lap up the good times.
Can I rent a house with a pool in Kenwood?
Tick the "pool" box in our handy filter tool and you can choose from 44 houses with private pools in Kenwood on Vrbo. Morning dip, sunset soak or midnight swim? Leisure activities are up to you when your holiday property comes with a swimming pool.
What are popular rental amenities in Kenwood?
Some of the most popular rental amenities guests are looking for in Kenwood are a fireplace, a firepit and a barbecue grill. Whether you're going on holiday with buddies, family or even pets, Vrbo holiday homes include the best amenities for chilling out with your loved ones.
Are there large group holiday rentals in Kenwood?
With 11 holiday rentals that can sleep 10 guests or more in Kenwood, there's no need to keep your invite list short. From family holidays to events like Thanksgiving or Christmas parties, Vrbo will help you find a large group rental to match the occasion.
Are there holiday rentals in Kenwood that welcome kids?
With 73 family-friendly holiday rentals available in Kenwood, now is an awesome time to introduce the kiddos to the wonders of travel. Simply check our "Properties good for families" filter box to find stays that come with conveniences perfect for families on the move, like full kitchens, private pools, hot tubs and bunk beds.
What are the top attractions for families in Kenwood?
There are loads of fabulous things to do and see with the family in Kenwood, such as:
  • Mortons Warm Springs
  • Robert Ferguson Observatory
  • Jack London State Historic Park
Are there one-bedroom holiday rentals in Kenwood?
Yes, there are nine one-bedroom properties in Kenwood to pick from. A one-bedroom holiday home is a great choice if it's just you and your partner or if you're travelling on your own. Toss in more space, convenience and privacy compared to a hotel, and you're sure to have an unforgettable break.
Can I find two-bedroom holiday rentals in Kenwood?
Take your pick of 16 two-bedroom holiday homes in Kenwood. Give the kids the second room or maybe fill it with a couple of your besties. There's space for whoever's fortunate enough to be joining your journey.
Are there holiday rentals with WiFi in Kenwood?
Whether you want to keep up with the latest news, reply to emails or surf social networks, there are 34 holiday homes with WiFi in Kenwood. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in Kenwood?
Select your travel dates and then use the filter tool to see holiday rentals with ac in Kenwood on Vrbo. With 66 air-conditioned properties available, you can enjoy a cool and comfortable stay.
How old do you have to be to rent a holiday rental in Kenwood?
The minimum age is typically 16, 18 or 21. It can differ from property to property on Vrbo, so look at the rules of your preferred Kenwood holiday rental before booking.
How long can I rent a holiday rental in Kenwood for?
The amount of time you can stay in a Kenwood holiday rental for is up to each property. Just tap in your preferred travel dates to browse options that offer extended stays. They have all the things you need to make your extended trip more comfortable and convenient, like kitchens and backyards. Some holiday homes might also offer discounted weekly or monthly prices, so you can hang around longer for less.

More holiday ideas