Vacation rentals with a pool in Windsor

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Top-rated rentals with a pool in Windsor

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Superhost

Home in Guerneville

4.83 out of 5 average rating, 178 reviews

Lovely and Spacious Ranch-Style Home With a Poolside Oasis

Savor outdoor suppers under a forest skyline in this wine country ranch. A lush, treelined perimeter encloses a shaded patio area featuring furnished terraces, a fire pit, and a central pool. Warm up in the hot tub after an evening swim. The layout of the house is unique. Each section of the house provides its own artistic and cozy energy. You can access the entire house except for the garage. I'm available 24/7 for any questions and needs. Guerneville is a small, rustic community nestled in the Russian River Valley. Sample local varietals at some of the world's finest vineyards or hike into the towering Redwood Forest. The town of Guerneville offers an array of fine local eateries. Please call me when you arrive and I'll walk you through the details of the home and the town!

Top guest favorite

The home is set among lush vineyards, framed by trees. A swimming pool is visible beside the house. Sunlight casts a warm glow over the expansive property, showing the rolling hills of the vineyard in the background.

Home in Glen Ellen

4.96 out of 5 average rating, 188 reviews

Vineyard Home - Featured in Top Publications

WHY YOU'LL LOVE IT - Stay on a private vineyard & walk to wineries - Stunning setting with pool, hot tub & bocce ball court - Prime location—just minutes to world-class wineries, top restaurants & luxury spas - Exclusive Perk—complimentary tastings at the Estate Winery next door - Chef-ready fully stocked kitchen - Ultra high-speed WiFi AS FEATURED IN Condé Nast Traveler | House Beautiful | House & Garden | The Wine Daily | Esquire | The Bold Italic | Refinery 29| Bon Traveler | Sunset Magazine

Top guest favorite

Home in Kenwood

4.99 out of 5 average rating, 300 reviews

4/3 Vineyard Home With Pool & Views (Sleeps 8)

1 King bedroom; 2 Queen bedrooms; 1 sleeping den with two twin beds; 3 full baths. One of the loveliest spots in Sonoma Valley. Stunning views of vineyards and mountains. Swimming pool and hot tub. Bocce Ball court through olive trees. Interior designer furnishings. Gourmet kitchen overlooking pool and vineyard. Wineries nearby. Beautiful lawn surrounding pool. Two acres. Fire pit overlooking vineyards. Perfect for friends & families in town for lazy weekends or Wine Country weddings.

Guest favorite

A spacious backyard features a seasonal pool, surrounded by a tiled deck. Comfortable seating arrangements include several adirondack chairs around a fire table. A dining table is set nearby, offering an inviting space for outdoor meals. Lush greenery adds a touch of privacy.

Home in Sonoma

4.99 out of 5 average rating, 232 reviews

Sonoma Valley Vacation Home with Seasonal Pool

Enjoy indoor/outdoor living in Sonoma Valley with tons of amenities! Our home has a comfy, modern interior with 3 private bedrooms, office room with twin daybed, 2 full baths, large dining room, fully equipped kitchen and 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, & eateries. Walking distance to a park, cafe, mexican restaurant, and 7-11 store.

Guest favorite

A swimming pool is surrounded by a wooden deck featuring four lounge chairs and shaded by green umbrellas. Lush greenery and flowering plants enhance the privacy of the area, with a gas grill positioned nearby.

Home in Sonoma

4.83 out of 5 average rating, 381 reviews

Family Home - Heated Pool, Hot Tub, bikes, + more!

Pool heated year round. Nov-April by request only. Book w/confidence! Buy trip Insurance! Ask for details. Pets welcome. Melt in the hot tub, cool off in the pool, dine on the deck as the sun sets. Inside, 4 skylights & an open layout give a real sense of space & light. Brew Peet's coffee while listening to songs on the Bose stereo. Bike to town, wineries & restaurants. Enjoy a game of ping pong. Sit under the stars by the fire pit. - 1 pet $100. 2nd pet $50 - signed rental agreement required

Guest favorite

Home in Windsor

4.97 out of 5 average rating, 199 reviews

Luxury Wine Country Estate with pool & hot tub

Welcome to our amazing Wine Country oasis, perfect for your relaxing getaway! This home features a large chef’s kitchen, four spacious bedrooms, and two living rooms. Enjoy the outdoor amenities, including large pool, hot tub, outdoor kitchen, bathroom, and dining area. You can also play a game of pool or pingpong in the finished garage! This home is located close to the Sonoma County Airport, wineries, and world-class dining, making it the perfect choice for enjoying all wine country offers

Superhost

A serene backyard features a spacious swimming pool, surrounded by lounge chairs and an umbrella for shade. The house stands in the background, with windows glowing warmly. Lush green trees line the perimeter, enhancing the tranquil atmosphere of the outdoor space.

Home in Santa Rosa

4.87 out of 5 average rating, 221 reviews

Hot Tub/Pool ~ Walk To Wine, Shops & Restaurants

Escape to our Mid Century Modern home in beautiful Sonoma Wine Country, a 10 min drive to some of the best wineries in the world! Relax in the large pool & hot tub, by the Traeger grill for BBQ dinners - where pets are welcome! Walking distance to Howarth Park, Spring Lake, in the neighborhood of Annadel State Park for hiking & biking. One block from Montgomery Village, full of boutique shops & Wine-Country restaurants. A 20 minute drive to Sonoma, & near Healdsburg, Kenwood + Bodega Bay.

Guest favorite

Home in Healdsburg

4.91 out of 5 average rating, 107 reviews

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.

Guest favorite

A swimming pool is featured with a bright blue surface, reflecting the surrounding greenery. A set of steps leads into the pool, and a diving board is positioned at the edge, providing an inviting space for relaxation and enjoyment.

Guesthouse in Santa Rosa

4.88 out of 5 average rating, 172 reviews

2 Wine Country Gem 2 Bedroom Upstairs

Looking for a place to stay in Santa Rosa that offers comfort, convenience, and charm? Look no further than our cozy guest house, located in a private gated property. You’ll have your own entrance and access to a shared laundry room with supplies. Enjoy the use of our pool, barbeque, and outdoor kitchen and seating area, where you can relax and soak up the sun. And as a special treat, you’ll get to savor our private tiffin service that delivers delicious home-cooked meals too.

Guest favorite

A spacious spa pool is nestled among a lush garden, with relaxing water jets visible. The outdoor area features a gravel path winding through greenery, lounge chairs, and seating arrangements. Soft lighting from lanterns provides a warm ambiance as trees surround the setting.

Home in Glen Ellen

4.91 out of 5 average rating, 176 reviews

Luxury home, hot tub/spa pool, 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.

Superhost

A serene pool area is framed by natural stone and lush greenery. Comfortable lounge chairs are positioned beside the sparkling water, while umbrellas provide shade for outdoor seating. The main house and a separate structure are visible in the background, set amidst vibrant autumn leaves.

Home in Sebastopol

4.91 out of 5 average rating, 103 reviews

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

This wine country luxury retreat is a perfect venue for a family or small group escape. Includes a 2 level main house with 3 bedrooms, a large pool, hot tub and separate pool house. Plus wine cellar/game room, work area, family room, gourmet kitchen, five gorgeous stone fireplaces, and a patio kitchen with a gas range & dining area. This beautiful property feels like your own private resort, set on nearly 4 acres including gardens and spectacular views of Mt St Helena.

Guest favorite

A serene swimming pool is visible in the foreground, surrounded by a spacious deck and well-maintained landscaping. The back of the house features large windows, allowing natural light to fill the interior. Umbrella-covered seating is positioned poolside, providing a welcoming outdoor space.

Home in Sonoma

4.88 out of 5 average rating, 302 reviews

*Heated* Swimming Pool Retreat Near Sonoma Square

We're thrilled to share our house in Sonoma with you! There's a heated swimming pool, a beautiful and quiet setting, and we think it's the best location for exploring Sonoma wine country. The home is 1.5 miles to Sonoma Square with a year-round heated swimming pool. Pool has an automatic safety cover that keeps the pool warm and makes it perfect for families with children. And great proximity to wineries, restaurants and all that Sonoma has to offer!