
Vacation 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.

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.

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.

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!

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.

Pacific Gardens Retreat
Enjoy a tranquil art filled garden escape at our pet friendly home! Whether you are soaking in the hot tub after a day of wine tasting or having dinner with friends this indoor/outdoor living retreat will leave you feeling relaxed. Well stocked kitchen, fast wifi and walking distance to downtown. Great restaurants and breweries nearby. Well behaved non destructive pets are welcome in this home. It may not be a fit if you have severe allergies though we do our best to clean very thoroughly.

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

Vineyard Vista, Modern Farmhouse Cottage with Pool
Our architect remodeled (2021), five star, elegant Farmhouse with great room and fireplace, is simply perfect throughout. This unique wine country two-acre property, with heated swimming pool (for a fee), looks out to the beautiful Russian River vineyards and the never-ending Western panorama. Only minutes from award winning food and shopping in downtown Healdsburg, it’s within easy walking or bicycling distance of tasting rooms at J, Rodney Strong and other acclaimed Sonoma wineries.

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.

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

Wine Country Gem - Sonoma Cottage with Pool Oasis
Charming Sonoma cottage perfect for a romantic getaway, girls’ trip, or family stay. Explore Sonoma, Glen Ellen & Napa with ease. The private unit has gourmet appliances, a minimalist-country style, and its own deck with dining + lounge seating. The peaceful 1-acre property features vineyards, a large saltwater pool, a veggie + herb garden, and fruit trees. Relax, recharge, and enjoy the best of wine country living. TOT #3140N
Popular amenities for Kenwood rentals with a pool
House rentals with a pool

Farmhouse at Sonoma Oaks: Hot Tub · Pool · Bocce!

Modern mid-century-inspired, Deer Ranch

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

Vineyard-House Escape in Sonoma Wine Country

Wine Country Retreat- Privacy-Spa/Pool/Games

Nice Wine Country Family Home

Sebastopol Gem, The Birdhouse. Hottub. Pool. Views

Cozy Home w/ Hot Tub/Pool- near Shops, Wine, Food
Condo rentals with a pool

Silverado Resort Dual Suite golf course villa

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

Book Now For Easter Weekend!
Other vacation rentals with a pool

Wine Country Farmhouse with pool & spa

707 BARREL LOUNGE Cottage

Petaluma Wine Country relaxing get away w/pool/spa

Oak & Vine: Pool | Hot Tub | Fire Table | BBQ | EV

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

When in Glen | Views | Pool & Hot Tub

Oak Den - Secluded Charm in the Heart of Sonoma

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 | $661 CAD | $636 CAD | $640 CAD | $683 CAD | $726 CAD | $851 CAD | $762 CAD | $795 CAD | $787 CAD | $880 CAD | $840 CAD | $720 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 |
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 710 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!
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