
Holiday rentals with a pool in Kenwood
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Top-rated rentals with a pool in Kenwood
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Sonoma Valley Vacation Home with Seasonal Pool
Gather indoors and outside at our Sonoma Valley rancher with tons of amenities! Inside, find a comfortable modern interior with 3 private bedrooms, office room with twin daybed, 2 full baths, large dining table, a fully equipped kitchen and breakfast/bar table. The backyard has a large pool (seasonal), gas bbq, fire table, seats and dining table. Minutes by car to Sonoma Square, Glen Ellen, wineries, hiking trails, spas, shopping and dining. Blocks to a park, cafe & two local favorite eateries.

Wildwood Retreat and Pool
The Wildwood Retreat is located on a wooded 2 acre country property in the hills above Sonoma just minutes from the Historic Downtown Sonoma Plaza. The newly remodeled studio apt is very private on a separate level below the main house conveniently close to the pool. Amenities include a king size bed, kitchenette, private bath,sunny deck,pool access and convenient parking. Great walks are just outside your door. This tranquil retreat is ideally located for enjoying all the Wine Country offers.

Designer Sonoma Getaway with Pool, Hot Tub & Bocce
Thornsberry House is a luxe Wine Country home nestled between the two oldest wineries in California while just 5 minutes from the Sonoma Square. Renovated to accommodate the most discerning traveler, it consists of two separate buildings connected by a breezeway and large deck. Situated on the east side of town, it offers a true escape where one can walk or bike down to Gundlach Bundschu at the end of our street, or soak up the afternoon light from the heated pool, hot tub or a game of bocce.

Spectacular Stone Pool/Spa with Views; Near Plaza
A spectacular stone pool and spa with bubbling stream compliments the warm and welcoming Summers House. (Please see notes below regarding pool and spa fees.) The house exudes charm. Sweeping views reach to the San Francisco Bay. Art, antiques and books create an embracing ambiance. Nestled into three, private wooded acres, Summers House is near wineries, and just 10 minutes from Sonoma Plaza restaurants, shops, and events. Well equipped kitchen, great dining spaces, large deck, comfy beds.

Private 1+ acre, Bocce, Waterfall, Free Pool Heat
With over 1 acre of flat wooded land, this private gated country estate is still just a few minutes from conveniences like Whole Foods and Safeway. And with a full-size bocce court, pool table, and dining pavilion, you might not want to leave. Our new saltwater pool and spa are gas-heated to be comfortable all year, at no extra charge. A rock river and pool waterfall add to the sound of rushing water. The house is a few minutes from downtown, and within 20 minutes of the highlights of Sonoma.

Spring getaway in beautiful Sonoma Valley!
Escape to your home-away-from-home on a private residential compound: the perfect getaway spot in the heart of beautiful Sonoma Valley! 🏡 Why You’ll Love It: ✔️ Minutes to 25+ wineries & great restaurants ✔️ Easy drives to Sonoma, Calistoga, Healdsburg, Napa & the Coast ✔️ Great hiking in nearby parks ✔️ Birdwatching in the garden ✔️ Saltwater pool & bocce court ✔️ Stunning Mountain views ✔️ Private patio with gas grill & outdoor dining ✔️ Full kitchen, separate bedroom with ensuite bath

Happy House Getaway - Pool, Hot Tub & Wine Country
Happy House – Year-Round Sonoma County Getaway with Pool & Hot Tub Welcome to Happy House, a comfortable, clean, and welcoming home—perfect for a Sonoma County getaway any time of year. Ideal for wine tasting, visiting local breweries, hiking, mountain biking, plus weekend escapes, or remote work. 🌿 Private Backyard Large yard with pool, hot tub, and easy parking. 🍽 Fully Stocked Chef’s Kitchen 🛋 Seasonal note: Outdoor cushions/umbrellas stored late Oct–mid May. Permit # SVR25-160

Eco Luxury Private Sanctuary / The Farmhouse Oasis
**Very Important** Please read description below and “Other things to note” at the bottom of this section before contacting us. • Adults Only • Private Sunny 1 Bedroom, 2 full bathroom 900 sq ft stand alone home • Private Backyard with Pool, Sauna, Outdoor Shower, and Outdoor Bathtub • Luxurious Modern Farmhouse Style • Created to feel like a boutique hotel experience • In the heart of wine country Sebastopol/ West Sonoma • Eco-Friendly products used • Strict cleaning protocols

Nice home, wineries, heated pool, hottub fire pit
This newly remodeled home is your perfect vacation rental. It features a heated pool for you to enjoy year round! There is also a brand new hot tub for an extra dose of relaxation. Enjoy your meal outside around the fire pit table or in the large open kitchen area of the home. If you want a little more privacy, there is an additional side yard with its own fire pit for you to sneak away to. With its prime location (only 20 min to Sonoma) this is the Wine Country home for you!

Eclectic Hideaway with Backyard Pool & Hot Tub
Embrace the blissful ambiance of this tastefully appointed retreat. The home features terraced living areas, rustic wood accents, an array of furnishings and decor, central heat and air conditioning, well supplied kitchen and a backyard patio with a dining space, lounges, gas grill, a solar heated pool and a hot tub. The house is located on a small, private cul-de-sac. NO PARTIES: including bachelor, bachelorette, wedding rehearsal dinners, etc.

Vineyard Retreat • Walk to Wineries • Press Pick
WHY YOU'LL LOVE IT - Stroll your own private Sonoma vineyard - Resort-style outdoor living: pool, hot tub & bocce court with vineyard views - Prime location: minutes to top wineries, dining, spas & shops - Exclusive perk: complimentary tasting at the estate winery next door - Chef-ready, fully stocked kitchen - Stylish interior with thoughtful amenities - Ultra-fast, reliable WiFi - Seasoned Superhost—responsive, reliable, and thoughtful

Idyllic Sonoma Vineyard Farmhouse With Pool
Immerse yourself in wine country! The "Bottage" is a recently updated farmhouse style 2 bedroom, 1 bath home, set on 2.5 acres with 2 acres of Pinot Noir vineyard. It is also walking distance to tasting rooms, the popular Lou's Luncheonette and Hanson's Distillery. It is conveniently located on one of the most popular biking routes in Sonoma, only 5 miles to the Sonoma Square, 10 miles to Napa, and 40 miles to San Francisco.
Popular amenities for Kenwood rentals with a pool
House rentals with a pool

Modern mid-century-inspired, Deer Ranch

Modern Log Cabin w/ Pool, Spa & FP Near DT & River

The Ranch

Vineyard-House Escape in Sonoma Wine Country

Sonoma Ranch, private pool on 7 acres!

Nice Wine Country Family Home

Luxury home (+ pool house) with views, pool & spa

Sebastopol Gem, The Birdhouse. Hottub. Pool. Views
Condo rentals with a pool

Silverado Resort Dual Suite golf course villa

Silverado! Luxe King Suite Mountain View Balcony

Remodeled Napa, CA Silverado Golf Course Condo

Wine Country Living at it's best at Silverado CC

Casa Vina at Silverado Resort and Spa | Fireplace

Romantic Luxurious Resort in Napa Valley, Sleeps 4

Fairways Silverado Golf and Country

1 bed | 1 bath | Silverado Resort Experience
Other holiday rentals with a pool

Wine Country Farmhouse with pool & spa

Farm Cottage With Private Pool

Wolf Ridge Sonoma Mountain Retreat

[Egg Farm Ranch] Heated Pool-Water Slide-Hot Tub

When in Glen | Views | Pool & Hot Tub

Spacious wine country villa with pool

Kenwood Vista by AvantStay | 7acres, Vineyard View

Romantic Tropical Garden Casita
When is the best time to visit Kenwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $683 AUD | $657 AUD | $662 AUD | $706 AUD | $750 AUD | $879 AUD | $788 AUD | $822 AUD | $814 AUD | $909 AUD | $868 AUD | $745 AUD |
| Avg. temp | 10°C | 10°C | 11°C | 11°C | 12°C | 13°C | 14°C | 14°C | 15°C | 13°C | 12°C | 10°C |
Quick stats about holiday rentals with a pool in Kenwood

Total holiday rentals
Explore 30 holiday rentals in Kenwood

Nightly prices starting at
Kenwood holiday rentals start at $186 AUD per night before taxes and fees

Verified guest reviews
Over 710 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Kenwood holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Kenwood rentals

4.9 Average rating
Kenwood stays are highly rated by guests—averaging 4.9 out of 5!
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