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

Tropical Oasis with Pool & Hot Tub 30min to Sonoma
This tropical oasis is located right in the heart of wine country, featuring 4 bedrooms, 4 full bathrooms, an in-ground pool, hot tub, waterfall with a fire pit, beautiful fireplace in the living room, and an open floor plan perfect for spending time with family and friends. Located just down the road from Anadell State park and the local Bennet Valley golf course; just minutes to downtown Santa Rosa featuring restaurants, bars, shopping and more. Only 30 min to Sonoma and 20 min to Healdsburg.

Wine Country Retreat- Privacy-Spa/Pool/Games
Take it easy at this unique & tranquil getaway in the middle of wine country! Feel worlds away but just minutes to world-class wineries, restaurants & shopping. Enjoy your own private pool, spa & game room. The large private property is perfect for your family getaway, couples retreat, or those looking for their own slice of heaven with thoughtful amenities. You'll want to come back year after year! Separate 1/1 guest house not included in price but available upon request at time of booking.

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.

Winter special on now 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.

707 BARREL LOUNGE Cottage
LIVE ALOHA IN SONOMA! Enjoy this tropical Hawaiian Getaway in the Heart of Sonoma Wine Country. Sonoma is a great little town to eat, drink, shop, hike, bike, walk, swim, and relax. There is so much to do here! This cottage will put you in a vacation state of mind as soon as you arrive. Relax around the pool, enjoy a good book, walk into town or hire a car service and visit some of the many amazing wineries in the Sonoma-Napa-Alexander Valleys. COME ENJOY ALOHA IN SONOMA!

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
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!

Wine Country | Pool & Spa | Park Views | Fast WiFi

Nice Wine Country Family Home

Cozy Home w/ Hot Tub/Pool- near Shops, Wine, Food

Silverado Napa Remodeled 3 bed 2 bath

Pacific Gardens Retreat
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

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
Other holiday rentals with a pool

Wine Country Farmhouse with pool & spa

Relax & Recharge at Hoff Lane

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

Arches - Olive Grove Cottage

Idyllic Sonoma Vineyard Farmhouse With Pool

Spacious 3-Bedroom Retreat in Santa Rosa

When in Glen | Views | Pool & Hot Tub

Oak Den - Secluded Charm in the Heart of Sonoma
When is the best time to visit Kenwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $680 AUD | $655 AUD | $659 AUD | $703 AUD | $747 AUD | $876 AUD | $785 AUD | $819 AUD | $810 AUD | $906 AUD | $864 AUD | $742 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 $185 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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