Vacation rentals in Kenwood

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Top-rated vacation rentals in Kenwood

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Guest favorite

Guesthouse in Kenwood

4.94 out of 5 average rating, 198 reviews

Casa de Vincenzi

Beautiful, immaculate private studio, situated in Kenwood village with separate entrance and garden patio offers a quiet retreat in the heart of Sonoma Valley. Walking distance to world class tasting rooms and restaurants. Close to Sonoma, Glen Ellen and fave parks. Enjoy your ensuite bathroom with fluffy towels and toiletries. Indoor or outdoor dining to enjoy wine, tea, conversation, TV or wifi. Sleep in the quiet of your comfy queen size bed. TOT (Transient Occupancy Tax) included. TOT #3720N

Sep 2 – 9

R4,475 ZAR per night

Guest favorite

Guesthouse in Glen Ellen

4.91 out of 5 average rating, 931 reviews

Crow Cottage ~ 3 min walk to town - restaurants

Crow Cottage is newly rebuilt and decorated in an eclectic whimsical style by the artist owners. It is light and airy with a private shade deck and sunny patio. The Cottage has a queen bed. There is a portable A/C. The cottage is well insulated so it doesn't get too hot in the summer. There is also a fan. Set on a country lane just a 3 min walk to great restaurants & a gourmet market. While we do have rescued cats in our yard we don't let them in any of the rooms. If highly allergic, reconsider.

Oct 29 – Nov 5

R2,671 ZAR per night

Guest favorite

Guest suite in Santa Rosa

4.97 out of 5 average rating, 181 reviews

Wine Country Retreat

Nestled in an upscale leafy neighborhood with stunning views of Spring Lake Regional Park from the deck. This bright, air conditioned, space comes with its own deck and propane grill for your sole use. The cottage also has a kitchen with a refrigerator, range, dishwasher, microwave, toaster oven, Keurig coffee maker etc. We also have a washer and dryer in the property and a tv. The cottage has its own entrance and is attached to the main house. It's not a detached unit. TOT account #1847

Jan 25 – Feb 1

R2,869 ZAR per night

Guest favorite

Home in Kenwood

4.99 out of 5 average rating, 270 reviews

Sonoma Vineyard Home With Pool & Stunning Views

In one of the loveliest spots in Sonoma Valley. Stunning views of vineyards and mountains beyond. New, modern swimming pool and hot tub. Bocce Ball court through olive trees. Interior designer furnishings. New gourmet kitchen overlooking pool and vineyard. Dozens of wineries nearby. Beautiful lawn surrounding pool. Two acres. Fully updated with all new furniture. Fire pit overlooking vineyards. Perfect for friends & families in town for lazy weekends or Wine Country weddings.

Dec 30 – Jan 6

R21,330 ZAR per night

Guest favorite

Home in Kenwood

4.88 out of 5 average rating, 412 reviews

Carriage House at Hamilton Family Vineyards

Stay among the vines in our renovated Carriage House. Located on our working vineyard in the heart of Sonoma Valley, you’ll love our updated Carriage House’s vintage, wine country charm, while appreciating its modern amenities. Relax in your private outdoor space, or enjoy some friendly competition on our Bocce court. We’d also love to invite you to visit our tasting room just a few minutes away. A short walk through the vines takes you on to other world class wineries and restaurants.

Dec 11 – 18

R6,091 ZAR per night

Guest favorite

Guest suite in Glen Ellen

4.96 out of 5 average rating, 191 reviews

Hummingbird Hideaway, Glen Ellen in Sonoma Valley

Hummingbird Hideaway is the perfect location to enjoy everything wine country has to offer. Located in the heart of Glen Ellen in the Sonoma Valley, you can stroll to wine tasting, restaurants, French Bakery, gourmet market and historic saloon for a night cap. Hiking the trails at the Jack London State Park is just minutes up the road. When you're ready to venture further, Sonoma is a short 15 minute drive, Kenwood is 10 minutes and just an hour to Bodega Bay on the Coast.

Jun 11 – 18

R2,943 ZAR per night

Superhost

Home in Kenwood

4.85 out of 5 average rating, 194 reviews

Heiter House- hot tub, views, & nearby wineries

This 2 bedroom 2 bathroom jewel sleeps 4 and provides everything needed for a perfect stay in the heart of Wine Country. A well-equipped kitchen, fast Wifi SMART TV, ping pong(located in garage), 2 garages, a deck with great sunrises, AC in the bedrooms - it's all there. The lovely town of Kenwood is minutes away by car, as are some of the best vineyards in the area. Both Sonoma and Santa Rosa can be reached within 20 minutes, making this the perfect base for any trip.

Sep 16 – 23

R8,633 ZAR per night

Guest favorite

Guest suite in Glen Ellen

4.94 out of 5 average rating, 180 reviews

Wine Country Harvest Hideaway-Private entry/space

Welcome to our Harvest Hideaway! We’re centrally located in the heart of Sonoma Valley, right in downtown Glen Ellen. We are walking distance to restaurants, tasting rooms, and the great Glen Ellen Village Market. With dozens of wineries nearby, we are a 10 minute drive to Kenwood, and 15 minutes to the Sonoma Square. Within an hour, you can be on the coast in Bodega Bay or on the Golden Gate Bridge entering San Francisco. We are sure you'll have a fantastic stay!

Mar 24 – 31

R3,267 ZAR per night

Guest favorite

Home in Kenwood

4.98 out of 5 average rating, 166 reviews

Sonoma Valley Getaway

Sonoma Valley Getaway is your perfect wine country home! Located in a quiet neighborhood in the quaint village of Kenwood, it is within walking distance to several tasting rooms, restaurants and parks. Dozens of world class wineries are just minutes away by car. For more exploring, the Napa Valley is a scenic 30 minute drive through the valley vineyards. Book now and come enjoy our contemporary 2 bed, 2 bath home with vineyard and mountain views!

Jul 1 – 8

R8,429 ZAR per night

Guest favorite

Guest suite in Santa Rosa

4.99 out of 5 average rating, 325 reviews

The Suite Life! Permit Number#SVR22-078

Our private Airbnb is an extremely comfortable guest suite of over 700 square feet with air conditioning and a gas fireplace. It's beautifully decorated with a large sofa and dining area. You'll have complete privacy with your own entrance and parking space plus free WiFi. Located in a beautiful area. World class wineries, and parks are minutes away. Please feel free to message Janette with any questions about the suite! Permit Number#SVR22-078

Sep 28 – Oct 5

R2,668 ZAR per night

Guest favorite

Cottage in Kenwood

4.99 out of 5 average rating, 237 reviews

Best Sonoma Location for Wine Country Vacation

Enjoy your stay in our charming guest cottage on a private, peaceful residential compound in Kenwood. Close to 25 wineries/tasting rooms and great restaurants w/in 5 minute drive. Bring a glass of wine to the bocce court, watch the local birdlife and the sun setting on the mountain. Hike in nearby regional and state parks. One hour from San Francisco, 12 miles to Sonoma Plaza and easy access to the coast, Napa, Russian River & Healdsburg.

Oct 5 – 12

R4,800 ZAR per night

Guest favorite

Cabin in Glen Ellen

4.97 out of 5 average rating, 625 reviews

Wine Country Cabin in the Woods

Enjoy the beautiful wooded area and our family owned historic cabin. Our gas fireplace, hot spa, fine bedding, and high speed wi-fi await. We're 10 min from wineries/dining in Kenwood and Glen Ellen in the heart of Sonoma Valley, adjacent to Napa Valley, with fantastic wineries, restaurants, breweries and 4 state parks with a free pass! We welcome friendly people of all backgrounds!

Mar 17 – 24

R3,426 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Kenwood vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Kenwood's top sights

VJB Cellars70 locals recommend

The Kenwood Restaurant & Bar57 locals recommend

Kunde Family Winery75 locals recommend

Cafe Citti46 locals recommend

TIPS Roadside37 locals recommend

Kenwood Inn & Spa8 locals recommend

Other great vacation rentals in Kenwood

Guest favorite

Guest suite in Santa Rosa

4.97 out of 5 average rating, 148 reviews

Private upstairs guest suite with queen bed

Dec 22 – 29

R2,186 ZAR per night

Guest favorite

Guesthouse in Sonoma

4.93 out of 5 average rating, 138 reviews

Cozy Sonoma Studio Nearby Wineries and Restaurants

Nov 9 – 16

R3,058 ZAR per night

Guest favorite

Farm stay in Petaluma

4.95 out of 5 average rating, 428 reviews

Sonoma Country Cottage, On 50 Acre

Jun 13 – 20

R2,638 ZAR per night

Guest favorite

Guest suite in Sonoma

4.91 out of 5 average rating, 344 reviews

Wildwood Retreat and Pool

Sep 9 – 16

R2,906 ZAR per night

Guest favorite

Cottage in Sonoma

4.99 out of 5 average rating, 147 reviews

Modern Farmhouse on Vineyard w Deck + Bocce Court

Jul 31 – Aug 7

R9,306 ZAR per night

Guest favorite

Home in Glen Ellen

5.0 out of 5 average rating, 171 reviews

Walk Everywhere! Quiet Wine County Retreat! Views!

Jul 21 – 28

R15,256 ZAR per night

Guest favorite

Guesthouse in Sebastopol

4.93 out of 5 average rating, 681 reviews

Sun Drenched Flat

Apr 14 – 21

R2,697 ZAR per night

Guest favorite

Guesthouse in Sonoma

4.96 out of 5 average rating, 444 reviews

Tranquil Wine Country Guest Cottage

Sep 20 – 27

R2,783 ZAR per night

Show all

Quick stats about vacation rentals in Kenwood

Total rentals
40 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
3.3K reviews
Nightly prices starting at
R1,731 ZAR before taxes and fees

Frequently Asked Questions

Do house rentals in Kenwood have a bbq area?
Absolutely! We offer over 20 house rentals with a bbq area in Kenwood. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Kenwood?
Experience the best of Kenwood with our house rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Kenwood have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Kenwood. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Kenwood?
Four-legged friends are welcome in Kenwood. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Kenwood?
Yes! Work meets play with ease at over 30 vacation rentals in Kenwood featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Kenwood vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Kenwood, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Kenwood have wifi?
Absolutely! We offer over 30 house rentals with wifi in Kenwood. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Kenwood?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with wifi, over 20 homes with a bbq area, over 30 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Kenwood

Top-rated vacation rentals in Kenwood

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Kenwood vacation rentals

Stay near Kenwood's top sights

Other great vacation rentals in Kenwood

Guest suite in Santa Rosa

Guesthouse in Sonoma

Farm stay in Petaluma

Guest suite in Sonoma

Cottage in Sonoma

Home in Glen Ellen

Guesthouse in Sebastopol

Guesthouse in Sonoma

Quick stats about vacation rentals in Kenwood

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Kenwood have a bbq area?

How much does it cost to stay in house rentals in Kenwood?

Do house rentals in Kenwood have air conditioning?

Are there pet-friendly vacation rentals in Kenwood?

Are there vacation rentals with a dedicated workspace in Kenwood?

Are there Kenwood vacation rentals on Airbnb with pools?

Do house rentals in Kenwood have wifi?

What are the most popular amenities for House Rentals in Kenwood?

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