Kenwood Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

279 Houses

31

4BR Retreat w/ Private Hot Tub, Fire Pit & 1 Acre of Country Charm

Sonoma County / Kenwood

Kenwood house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$759

Price per night from

$759

(22) Excellent 

18

Relaxing, Private Poolside Cottage for 2 in Sonoma Valley Wine Country

Sonoma County / Kenwood

Kenwood cottage

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Swimming pool

Price per night from

$224

Responds fast!
avg. 53 minutes

Price per night from

$224

24

4BR Vineyard House with Pool + Guest House in Kenwood

Sonoma County / Kenwood

Kenwood house

4 6 min stay varies

  • 4 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$1,016

Price per night from

$1,016

(6) Excellent 

25

Heiter House - the perfect getaway in Wine Country

Sonoma County / Kenwood

Kenwood house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$285

Price per night from

$285

(1) Excellent 

24

Spa, Bocce, Bbq Kitchen, Walk or Bike to Wineries

Sonoma County / Kenwood

Kenwood house

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Private garden

Price per night from

$384

Price per night from

$384

(4) Excellent 

23

WALK to Wineries from this Gorgeous Designer Home!

Sonoma County / Kenwood

Kenwood house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Nearest beach 52 mi
  • Child Friendly
  • Car not necessary

Price per night from

$516

Responds fast!
avg. 3 hours 48 minutes

Price per night from

$516

17

The Stone Lodge in Kenwood ~ 5 bedroom/5 bath

Sonoma County / Kenwood

Kenwood house

5 10 2 nights min

  • 5 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly

Price per night from

$3,079

Price per night from

$3,079

28

Gorgeous Vineyard-View 3BR on 6.5 Acres w/ Chef’s Kitchen, Pool & Hot Tub

Sonoma County / Kenwood

Kenwood house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$575

Price per night from

$575

27

2BR Sonoma Valley Vineyard-View Cottage w/ Loft—Private Hot Tub & Shared Pool

Sonoma County / Kenwood

Kenwood cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Ask about children

Price per night from

$616

Price per night from

$616

18

Peaceful Wine Country Vineyard Cottage with Pool & Hot Tub

Sonoma County / Kenwood

Kenwood cottage

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$571

Price per night from

$571

17

Villa LaFleur Sonoma

Sonoma County / Kenwood

Kenwood villa

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,713

Price per night from

$1,713

24

Idyllic 3BR, 2BA Sonoma House w/ Pool and Deck: Retreat into Wine Country

Sonoma County / Kenwood

Kenwood house

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$508

Price per night from

$508

(1) Excellent 

24

Poolside 3BR/4.5BA in Wine Country w/ Spa, Fitness Cabana & Bocce Court

Sonoma County / Kenwood

Kenwood house

3 8 5 nights min

  • 3 bedrooms
  • sleeps 8
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$580

Price per night from

$580

(10) Excellent 

31

Modern 3br Home W/Pool & Seasonal Creek in Sonoma.

Sonoma County / Kenwood

Kenwood house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Air conditioning
“A hidden wine country gem!” I spent a long weekend with my mother up in Wine Country and am so glad we chose Whispering Creek Getaway. First of all, I love the Sonoma County area of wine country, you're surrounded by vineyards but not stuck in all the
…see more

Price per night from

$630

Price per night from

$630

9

Bella Luna Suite at Casa Bella

Sonoma County / Kenwood

Kenwood cottage

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Pet Friendly

Price per night from

$342

Price per night from

$342

27

1BR Country Cottage with Vineyard & Valley Views—Hot Tub & Pool

Sonoma County / Kenwood

Kenwood cottage

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$422

Price per night from

$422

49

Casa Bella Estate in Wine Country

Sonoma County / Kenwood

Kenwood house

10 12 min stay varies

  • 10 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$1,371

Price per night from

$1,371

11

Bella Luna Cottage in Wine Country

Sonoma County / Kenwood

Kenwood house

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Child Friendly
  • Pet Friendly

Price per night from

$344

Price per night from

$344

19

Wine Country Retreat - Elegant & Comfortable Home

Sonoma County / Kenwood

Kenwood house

4 6 2 nights min

  • 4 bedrooms
  • sleeps 6
  • 2 nights min
  • Ask about children

Price per night from

$369

Price per night from

$369

50

Casa Bella Corporate Retreats in Wine Country

Sonoma County / Kenwood

Kenwood house

10 22 2 nights min

  • 10 bedrooms
  • sleeps 22
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$1,661

Price per night from

$1,661

Great rentals within 20 miles that match your search

Distance approx 18 km from Kenwood

15

THE BIRDHOUSE RETREAT WITH POOL AND HOT TUB

Sonoma County / Sebastopol

Sebastopol house

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Nearest beach 24 mi
  • Swimming pool
  • Child Friendly

Price per night from

$314

Price per night from

$314

Distance approx 4.23 km from Kenwood Show on Map

12

Harvest Hideaway

Sonoma County / Glen Ellen

Glen Ellen room

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min

Price per night from

$115

Price per night from

$115

Distance approx 15.06 km from Kenwood

(9) Excellent 

15

Charming Sonoma County Vacation Rental

Sonoma County / Sebastopol

Sebastopol house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 26 mi
  • Child Friendly
  • Private garden

Price per night from

$228

Price per night from

$228

Distance approx 13.97 km from Kenwood

(5) Excellent 

13

Little Bird Cottage, Perfectly Located

Sonoma County / Sebastopol

Sebastopol cottage

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$200

Responds fast!
avg. 3 hours 59 minutes

Price per night from

$200

Distance approx 8.93 km from Kenwood

(1) Excellent 

17

Annabelle's Cottage-Farmhouse chic in wine country

Sonoma County / Sonoma

Sonoma cottage

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Ask about pets

Price per night from

$189

Price per night from

$189

Distance approx 7.07 km from Kenwood

48

5BD Luxury Napa Valley Walk to Town Home

Napa Valley / St. Helena

St. Helena house

4 8 30 nights min

  • 4 bedrooms
  • sleeps 8
  • 30 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

Price per night from

$1,371

Price per night from

$1,371

Distance approx 16.66 km from Kenwood

(26) Very Good 

15

BJ's Nest~Tranquil Studio Apartment Retreat, w/Hot Tub. Close To Downtown Napa.

Napa Valley / Napa

Napa apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly
“Relaxing” My husband and I are early risers and love to hike, canoe and enjoy the outdoors as well as towns and wine tasting! Bj's nest was in a perfect location to come 'home' to and have wine and food and enjoy the fabulous weather on the porch or r
…see more

Price per night from

$229

Responds fast!
avg. 3 hours 41 minutes

Price per night from

$229

Distance approx 12.79 km from Kenwood

10

The Ultimate Wine County View Estate

Sonoma County / Healdsburg

Healdsburg house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Air conditioning
  • Private garden

Price per night from

$952

Price per night from

$952

Distance approx 12.28 km from Kenwood

16

Sonoma Vineyard - Two Bedroom Bocce Cottage!

Sonoma County / Sonoma

Sonoma cottage

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min

Price per night from

$316

Responds fast!
avg. 3 hours 12 minutes

Price per night from

$316

Distance approx 16.21 km from Kenwood

(31) Excellent 

58

Napa Retreat - Best View in Silverado

Napa Valley / Napa

Napa apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“High-End Comfort” This is the second time we stayed at this condo on Cottage Drive. It was even nicer and more luxurious than I remembered it. High end finishes, fully stocked kitchen, two bedrooms (with really comfortable beds, pillows and linens).
…see more

Price per night from

$451

Price per night from

$451

Distance approx 16.29 km from Kenwood

26

Premium Suite Located Right off the Golf Course in Beautiful Napa Valley CA

Napa Valley / Napa

Napa condo

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$205

Responds fast!
avg. 1 hour 24 minutes

Price per night from

$205

Distance approx 8.18 km from Kenwood

(1) Very Good 

9

Sonoma County Living ~ Casual Elegance

Sonoma County / Santa Rosa

Santa Rosa house

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 20 mi
  • Air conditioning
  • Private garden

Price per night from

$155

Responds fast!
avg. 3 hours 39 minutes

Price per night from

$155

Distance approx 19.26 km from Kenwood

(1) Very Good 

10

Napa - Studio Suite - Sleeps up to 4

Napa Valley / Napa

Napa condo

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$342

Price per night from

$342

Distance approx 15.43 km from Kenwood

4

Worldmark Windsor #4 Healdsburg Wine Country 3BR 2Ba Nice Resort Condo Sleeps8!

Sonoma County / Windsor

Windsor condo

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$457

Price per night from

$457

Distance approx 14.02 km from Kenwood

(1) Excellent 

8

Comfortable room

Napa Valley / Napa

Napa house

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Air conditioning
  • Private garden

Price per night from

$172

Price per night from

$172

Distance approx 10.37 km from Kenwood

13

Walk to Sonoma Square! Lovely Home in Wine Country

Sonoma County / Sonoma

Sonoma house

4 8 30 nights min

  • 4 bedrooms
  • sleeps 8
  • 30 nights min
  • Child Friendly

Price per night from

$402

Price per night from

$402

Distance approx 14.42 km from Kenwood

11

The Orchard House

Napa Valley / Napa

Napa apartment

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$568

Price per night from

$568

Distance approx 14.42 km from Kenwood

10

The Nest

Napa Valley / Napa

Napa studio

Studio 2 30 nights min

  • Studio
  • sleeps 2
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$212

Price per night from

$212