
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.

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.

Sonoma Valley Vacation Home with Seasonal Pool
Gather indoors and outside at our Sonoma Valley rancher with tons of amenities! inside, a comfortable modern interior with 3 private bedrooms, office room with twin daybed, 2 full baths, large dining table fork 8, fully equipped kitchen & breakfast/bar table. The backyard has a large pool (seasonal), gas bbq, fire table, seating and dining table. Minutes by car to Sonoma Square, Glen Ellen, wineries, hiking trails, spas, shopping and dining. Blocks to park, cafe & two local favorite eateries.

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

Sonoma Retreat as featured on CBS's Staycation
FEATURED ON CBS's STAYCATION WINE & DINE! Enjoy breathtaking wine country views and sunsets from Cavedale Ridge, a peaceful hillside retreat. On the vast Pool Deck off the Chef's Kitchen, swim, grill, dine, and relax in the spa. And, in the evenings, star-gaze around the Fire Pit. All four Primary Suites offer similar standards of accommodation: space, privacy, comfort and modern bathrooms. This makes Cavedale Ridge ideal for four couples, groups of adults, or extended family gatherings.

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

An Italian Villa in the heart of Napa Valley!
Villa RayEl was inspired by the farmhouses and small villas of Italy. Located midway between downtown Napa and Yountville, this property sits on 2 acres providing great privacy. It sits next to a year-round creek with a view of a vineyard and nightly sunsets. It has a pool and an attached hot tub. Located 5 minutes off Highway 29, 8 minutes to Downtown Napa and 8 minutes to Yountville. It is convenient to great wineries, restaurants. Its the perfect getaway for families and friends!

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!

Luxury home, heated spa tub, walk to restaurants
Luna Lodge, a 3 bedroom 2 bath Glen Ellen village luxury home in the heart of Sonoma wine country. The home has a beautiful garden with spa pool by a peaceful creek. Everything you need for a great vacation is at your fingertips. Situated on a quiet lane, 5 min walk to wine tasting rooms, top restaurants, food markets. Enjoy a gourmet private chef dinner while at the home. Let us know if you are interested and we will help you arrange a very special dining experience.

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.
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

Sonoma Ranch, private pool on 7 acres!

Nice Wine Country Family Home

*Heated* Swimming Pool Retreat Near Sonoma Square

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

Sebastopol Gem, The Birdhouse. Hottub. Pool. Views

Silverado Napa Remodeled 3 bed 2 bath
Condo rentals with a pool

Silverado Resort Dual Suite golf course villa

Silverado! Luxe King Suite Mountain View Balcony

Wine Country Living at it's best at Silverado CC

Romantic Luxurious Resort in Napa Valley, Sleeps 4

Casa Vina at Silverado Resort and Spa | Fireplace

Spring Escape | Silverado 2BR Golf Course View

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

Relax & Recharge at Hoff Lane

2bdr/2ba Silverado Resort : Gated + Golf Views

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

Idyllic Sonoma Vineyard Farmhouse With Pool

When in Glen | Views | Pool & Hot Tub

Kenwood Vista by AvantStay | 7acres, Vineyard View
When is the best time to visit Kenwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $685 AUD | $659 AUD | $663 AUD | $707 AUD | $752 AUD | $881 AUD | $789 AUD | $824 AUD | $815 AUD | $911 AUD | $870 AUD | $746 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 $187 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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