
Vacation rentals with a pool in Kenwood
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Kenwood

Total vacation rentals
Explore 30 vacation rentals in Kenwood

Nightly prices starting at
Kenwood vacation rentals start at $180 CAD per night before taxes and fees

Verified guest reviews
Over 820 verified reviews to help you choose

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

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
30 of Kenwood vacation rentals include wifi 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!
Top-rated rentals with a pool in Kenwood
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Pool - Hot Tub - Sauna | Wine Country Oasis Views
Imagine waking up to 180° panoramic views of the Sonoma Mountains, stepping onto a sun-warmed deck with coffee in hand, then spending the afternoon drifting between a solar-heated pool, a 5-person hot tub, and a cedar sauna — all without leaving the property. That's the everyday rhythm at this hillside wine-country retreat in Santa Rosa. The house was fully renovated top-to-bottom with the kind of high-end detail that makes you forget the outside world: radiant-heat concrete floors that warm yo

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.

Vineyard Haven: Pool, Hot Tub & Wine Country Charm
Property is managed by Inspired in Sonoma. Welcome to your private wine-country vineyard haven, nestled on an acre of quiet woodland in the heart of Kenwood, California—a serene pocket of Sonoma Valley where golden light filters through oak trees, and every day feels like a celebration of good living. This spacious elegantly appointed 3-bedroom house, swimming pool and Hot Tub invites up to eight guests to unwind, reconnect, and savor the beauty of Kenwood’s vineyards, tasting rooms, and parks.

Villa Annadel - Stunning 5 Bedroom with a Pool
Escape to your own private sanctuary at Villa Annadel. Savor the unparalleled privacy and modern sophistication of this one-of-a-kind wine country retreat. The expansive 3,200 square foot villa sits on just under 1.5 acres of privacy with a large sparkling pool, hot tub and outdoor dining gazebo. Game lovers will rejoice, from cornhole, to darts, ping pong and vintage arcade games. It’s easy to forget you are minutes from some of Santa Rosa’s finest restaurants and wine tasting destinations!

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.

Pool & garden 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

Vineyard Home | Walk to Wineries | Pool & Spa
WHY YOU'LL LOVE IT - Private Sonoma vineyard with stunning Wine Country views - Resort-style setting with pool, hot tub & bocce court - Walk to wineries; minutes to Sonoma & Napa tasting rooms, dining & spas - Complimentary tasting at the estate winery next door - Perfect for bachelorettes, wine weekends, celebrations, reunions & retreats - Chef-ready, fully stocked kitchen - Stylish interiors & thoughtful amenities - Fast, reliable WiFi - Seasoned Superhost—responsive, reliable & thoughtful

Modern wine country stunner with pool & pickleball
Enjoy the best of Sonoma from this recently remodeled home. On over 1 acre with mature beautiful landscaping. Just added pickle ball/sport court! New kitchen and baths. Designer finishes. Comfy beds. Spacious and private outside seating and dining. Gorgeous pool. Hot tub and bar area in converted container. Close to the finest wineries in Sonoma. 2 minutes from Sonoma Golf Club. 10 minutes to Sonoma Square, 20 on bike. 7 minutes to Glen Ellen. 10 minutes to Kenwood. Sonoma County TOT #4481N

Wine Country Villa Heated Pool Hot Tub Upper Level
Welcome to Brush Creek, 20-minutes from Sonoma, Napa, Russian River, Alexander, and Knight's Valleys. Our cozy villa offers 2 unique bedrooms, including a regal King Master suite and a second King bedroom. Complimentary EV charging. Healdsburg, Calistoga, and the trendy Barlow are easily accessible. Brush Creek: where comfort, luxury, and character converge for an unforgettable wine country retreat. Heated Pool (fees may apply). No one else in the property during your stay. SVR26-101

Wine Country Escape: Pool & Hot Tub. Fast WiFi
Escape to our stylish Santa Rosa home, your perfect base for wine country! Comfortably sleeps 8 with 4 bedrooms. Relax in the private backyard oasis featuring a pool, soaking hot tub, and a cozy gas fire pit under a gazebo. Centrally located near world-class wineries, breweries, and dining. Ideal for families and friends seeking a memorable getaway in a quiet, convenient neighborhood. We are happy to help plan your trip or arrange a private wine tasting at the house. Just ask!

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.

Wine Country Retreat | Pool, Hot Tub + Vibes
Summer-ready backyard + hot tub | Close to wineries 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
Popular amenities for Kenwood rentals with a pool
House rentals with a pool

Heated Pool, Hot Tub & Fire Pit in Wine Country

Wine Country Retreat- Privacy-Spa/Pool/Games

5-Bedroom Creekside Wine Country Retreat

Farpoint: Heated Infinity Pool, Mountain Views

Charming Home w Pool+Hot Tub. Walk to Shops & Wine

Eco Luxury Private Sanctuary / The Farmhouse Oasis

Vineyard Farmhouse w/ Pool & Mt. Helena Views

Eclectic Hideaway with Backyard Pool & Hot Tub
Condo rentals with a pool

Pool View Retreat at Silverado Resort 10 min to DT

Silverado! Luxe King Suite Mountain View Balcony

Silverado Resort - Private 3 Bedroom, 2 Bath Condo

Fairways Silverado Golf and Country

Silverado Resort Condo with Pool

2 bed I Silverado Resort & Spa in Napa - Wine Town

Fairway Escape | BBQ | Firepit | Golf Course View

♥Luxe 2BR, 2 patios, pool, 10 Min To Dwtn/wineries
Other vacation rentals with a pool

Sonoma Mountain Retreat

2 Wine Country Gem 2 Bedroom Upstairs

Romantic Tropical Garden Casita

Wine Country Gem - Sonoma Cottage with Pool Oasis

707 BARREL LOUNGE Cottage

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

Kenwood Vista by AvantStay | 7acres, Vineyard View

Private Vineyard | Pool | Chef's Kitchen | Kenwood
When is the best time to visit Kenwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $671 CAD | $717 CAD | $714 CAD | $913 CAD | $769 CAD | $814 CAD | $761 CAD | $794 CAD | $786 CAD | $879 CAD | $838 CAD | $719 CAD |
| 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 |
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