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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Top guest favorite

A serene pool area features a sparkling blue pool surrounded by lounge chairs under palm trees. The natural landscape offers rolling hills in the background, while soft lighting from string lights enhances the tranquil atmosphere as the sun sets.

Home in Forestville

4.99 out of 5 average rating, 123 reviews

Giusti Ranch, by Vinifera Homes

“An amazing property that exceeds any descriptions that can be provided. From the grounds to the house everything is first-class” - Michael. This 19-acre family-owned working ranch is the perfect setting for your wine-country adventure. Enjoy the surrounding views, refreshing pool, hot tub, gourmet kitchen & spacious great room. Located just mins. from renowned wineries & Michelin-starred restaurants, Giusti Ranch, A Vinifera Homes Property has everything you need for a truly memorable stay!

Guest favorite

The living room features comfortable chairs and a large TV mounted on the wall. A coffee table holds decorative items, and a record player is positioned nearby. Natural light enters through a skylight, enhancing the warm and inviting ambiance.

Home in Santa Rosa

4.93 out of 5 average rating, 127 reviews

PrivateWarm&Cozy+Spa+Pool+FirePit+Wifi!

Your home base for Sonoma, Napa, the Russian River and Sonoma Coast! A quiet neighborhood home within easy walking distance to shops and restaurants with many more options just a short drive away. Hundreds of wineries, breweries, and distilleries are here. Dozens of state and regional parks are waiting for you to explore. There's even a great neighborhood park just behind the house! Wondering what to do on your visit? My co-host Brenna and I are happy to help plan your trip to Wine Country.

Guest favorite

A private outdoor area features a hot tub adjacent to a wooden deck. A white dining table is positioned for meals, surrounded by lush greenery. Soft lighting hangs above, adding to the relaxed setting. A window on the house offers natural light to the space.

Home in Santa Rosa

4.97 out of 5 average rating, 155 reviews

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.

Top guest favorite

A serene outdoor space features a sparkling saltwater pool surrounded by lush greenery and colorful landscaping. A cozy cottage is positioned in the background, with a gray roof and welcoming entrance. Comfortable lounge chairs are arranged neatly beside the pool, inviting relaxation.

Cottage in Kenwood

4.99 out of 5 average rating, 260 reviews

Private Charming Poolside 1 BD/BA in 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

Top guest favorite

A serene pool area is framed by natural stone paving, with a wooden pergola enhancing the outdoor space. Lush greenery and shrubs provide a backdrop, while distant rolling hills can be seen in the background, adding to the scenic tranquility.

Guest suite in Healdsburg

4.93 out of 5 average rating, 451 reviews

Pony Ranch Vineyard Estate with Pool

Guest House with private entrance on gorgeous gated Vineyard Estate. Overlooks pool and vineyards with views to Mount St. Helena. Gas fireplace, refrigerator, microwave, Keurig coffee maker, queen bed. Seasonal private pool with fabulous views, occasionally shared with owners. Toilet and sink separate from shower. 8 minutes to the Healdsburg Plaza. Less than a mile from 3 wineries, very close to dozens more. Agricultural Education Programs available. Sonoma County TOT Certificate 1362N

Guest favorite

Home in Healdsburg

4.91 out of 5 average rating, 116 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.

Top guest favorite

A private pool area features a refreshing swimming pool surrounded by natural landscaping. A float is seen in the water, while the stand-alone home with large windows provides a charming backdrop. Potted plants add greenery to the serene outdoor space.

Home in Graton

5 out of 5 average rating, 660 reviews

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 covid cleaning protocols

Guest favorite

A dining area is showcased with a wooden table surrounded by six matching chairs. A light fixture hangs above, illuminating the space. The kitchen area is visible in the background, featuring wooden cabinetry and modern appliances against warm wall tones.

Apartment in Windsor

4.97 out of 5 average rating, 107 reviews

Pool + 4 Hot Tubs! Gym, Luxury 2 bedroom villa.

Two Bedroom Twins: King in master, twins in second bedroom, queen Murphy bed in living area. Maximum occupancy 6. Full Kitchen: Unit includes refrigerator, sink, range and dishwasher. Resort has Pool, Children's Pool, Hot Tub, and much more. ❤ Free Parking. Free Internet ❤ ★ If reserving a FRIDAY OR SATURDAY there is a 2 night minimum unless request is made last minute (3 days before check in)★ ★24 hour reception★ ★Calendars updated daily★ ★Multiple Units/Room Sizes Available★

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, 186 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.

Top guest favorite

The outdoor area features a large swimming pool surrounded by lounge chairs and umbrellas. A spacious barn-like structure is visible in the background, nestled among trees, while a hot tub is situated adjacent to the pool, creating a serene and functional outdoor retreat.

Home in Santa Rosa

4.97 out of 5 average rating, 110 reviews

Sustainable Luxury Barn - Secluded Sonoma Retreat!

Relax in the most beautiful, secluded setting Sonoma County has to offer. Hilltop views, walking trails right next to the property, and wineries so close, there is one just across the access road to the property. Constructed from trees that once stood where the Barn now stands, makes this property blend in with the natural surroundings. The trees were milled and dried on site. All siding, beams, flooring, basically anything made of wood is sourced from the property.

Guest favorite

An outdoor space features a plunge pool surrounded by a sun deck with lounge chairs and a sun umbrella. The home, with its wood accents, is set against a backdrop of tall redwood trees, contributing to a serene, natural setting.

Home in Occidental

4.96 out of 5 average rating, 159 reviews

Modern mid-century-inspired, Deer Ranch

Deer Ranch is a remodeled 2 bedroom, 1 bathroom home sitting on four acres of private land, with outdoor decks, hot tub, and plunge pool. This contemporary Frank Lloyd Wright-styled-like home sits on top of a hill with meadows below and towering redwoods that add to a peaceful seclusion getaway, and still only minutes from the hamlet of Occidental (1.3 miles). The pool is open during the summer months only (late May-end of September). The hot tub is on all year-round.

Superhost

A small, circular pool is surrounded by lounge chairs and umbrellas. In the background, the multi-story building features balconies and landscaped greenery. A playground and additional seating areas are visible beyond the pool, creating a welcoming outdoor space.

Apartment in Windsor

4.88 out of 5 average rating, 178 reviews

Windsor 2 Bed/2 Bath Condo ~ Pool ~ Hot Tub ~ Gym

***Condo: 1,023 square feet 2 bedroom/2 bath- King size bed in the master bedroom, two twin beds in the 2nd bedroom (can be put together to make a king), and one queen Murphy bed in the living room. Additional amenities include a full kitchen and dining area, gas fireplace, washer and dryer and a private terrace with gas barbecue. Maximum occupancy is six. *** twin beds in 2nd bedroom can be put together to make a king size bed. Please request in advance.