Vacation rentals with a pool in Windsor

4.99 out of 5 average rating, 132 reviews

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

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!

The outdoor space features a gazebo with a fire pit, surrounded by comfortable seating. Lounge chairs are positioned near an unheated pool, and a dining table with seating is visible in the background, creating a welcoming atmosphere for relaxation and gatherings.

4.93 out of 5 average rating, 142 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.

4.98 out of 5 average rating, 171 reviews

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 Junior College

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.

4.99 out of 5 average rating, 267 reviews

Cottage in Kenwood

Enjoy autumn and beyond 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

Guest suite in Healdsburg

A spacious guest house is set within a picturesque vineyard estate, featuring a distinct architectural style with multiple gabled rooftops. The driveway leads to a well-maintained entrance, surrounded by lush landscaping and mature trees, providing a serene and welcoming arrival experience.

4.93 out of 5 average rating, 462 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

4.92 out of 5 average rating, 119 reviews

A heated swimming pool reflects the early evening sky, surrounded by lush greenery. Comfortable lounge chairs are positioned around the pool, complemented by a shaded umbrella. The vineyard is visible in the background, enhancing the peaceful atmosphere of this outdoor space.

Home in Healdsburg

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.

4.97 out of 5 average rating, 110 reviews

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

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★

5 out of 5 average rating, 679 reviews

A private backyard features a solar heated swimming pool surrounded by lounge seating and potted plants. A tiki bar is visible in the background, with palm trees providing shade in the sunlight. The space combines relaxation and outdoor living for a serene atmosphere.

Home in Graton

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

4.87 out of 5 average rating, 187 reviews

A three-story building is seen with a colorful facade displaying verdant green, red, and yellow hues, surrounded by trees. The outdoor pool area features lounge chairs along the water's edge, illuminated against a night sky. The interior image shows a kitchen with wooden cabinets and dining space.

Apartment in Windsor

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.

4.97 out of 5 average rating, 210 reviews

Happy House Getaway - Pool, Hot Tub & Wine Country

Welcome to Your Relaxing Getaway! My home is a comfortable, clean, and happy space—perfect for unwinding and enjoying all that Sonoma County and the Bay Area have to offer. 🌿 Spacious Backyard: Large yard with a pool (heated by the sun) 6-person hot tub (kept at 102°F) Easy parking 🍽 Fully Stocked Chef’s Kitchen 🛋 Seasonal Note: Outdoor cushions/umbrellas stored late Oct to mid-May Come stay—you’ll love it! Happy House Permit #: SVR24-194

4.95 out of 5 average rating, 269 reviews

A modern cottage is set against a backdrop of vibrant landscaping, showcasing a large, clear salt-water pool. Various outdoor seating areas are visible, complemented by lush trees and greenery that enhance the serene environment.

Guesthouse in Sonoma

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

5 out of 5 average rating, 156 reviews

Bungalow in Rio Nido

BungalowTerrace-HotTub/Arcade/MassageChair/Gym

Welcome to the Bungalow Terrace! Step away into a magical journey full of life & color. A living 1950's Fairytale tucked high above the Redwoods. A place to dream peacefully, Live by the sun & Love by the moon. Designed for couples/families and any and all looking to treat themselves somewhere over the rainbow. The Bungalow Terrace is a sanctuary of magic, fun, and tranquility that will provide memories for a lifetime.

Popular amenities for Windsor rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.9 out of 5 average rating, 188 reviews

The exterior of a two-story California Craftsman home is shown, featuring a gabled roof and a welcoming front porch. Green lawn and garden beds with shrubs and flowers frame the pathway leading to the entrance, emphasizing the home's charming design.

Home in Junior College

Historic 1880's Craftsman Style Home with Pool.

4.85 out of 5 average rating, 104 reviews

A spacious outdoor area features a sparkling heated pool surrounded by a well-maintained garden. Comfortable lounge chairs are positioned nearby, and a fire pit with seating is highlighted, creating an inviting space for relaxation. Vibrant trees provide a serene backdrop to the setting.

Home in Sonoma

Sonoma Country Club Wine Country w/ pool

4.99 out of 5 average rating, 177 reviews

A private outdoor pool area features a sleek, blue pool surrounded by smooth stone tiles. Chaise lounges are positioned nearby, inviting relaxation. The setting is complemented by a rustic wooden structure and a charming home with a brick chimney, set against a colorful sunset sky.

Home in Sonoma

Vineyard-House Escape in Sonoma Wine Country

4.97 out of 5 average rating, 102 reviews

The image showcases a spacious swimming pool surrounded by a manicured lawn and lounge chairs. Two stylish cabanas are positioned beside the pool. Lush trees are visible in the background, complementing the modern design of the home with solar panels on the roof.

Home in Sonoma

Modern wine country stunner!

4.91 out of 5 average rating, 120 reviews

A spacious outdoor area features a large pool surrounded by natural stone walls. Comfortable lounge chairs are positioned for relaxation, and green umbrellas provide shade. Lush landscaping enhances the serene environment, with trees and plants framing the scene.

Home in Sebastopol

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

4.98 out of 5 average rating, 186 reviews

A lively pool area is featured, showcasing a clear blue swimming pool surrounded by lounge chairs and vibrant inflatable floats. A shaded cabana provides a relaxing spot, while a nearby umbrella offers additional shade. The surrounding landscape includes lush greenery and a stone wall.

Home in Sebastopol

Sebastopol Gem, The Birdhouse. Hottub. Pool. Views

4.86 out of 5 average rating, 118 reviews

A modern hillside lodge is surrounded by lush greenery, featuring a wrap-around deck adorned with string lights. Steps lead up to the entrance, with multiple levels of wooden decking providing serene outdoor spaces.

Home in Guerneville

Leo’s Lodge - Lux Retreat with Pool and Hot Tub

4.89 out of 5 average rating, 140 reviews

A serene infinity pool reflects vibrant sunset colors, with lounge chairs and umbrellas positioned nearby. The horizon displays a gradient of pinks and purples, creating a tranquil atmosphere against the backdrop of distant hills and valleys.

Home in Glen Ellen

Spectacular Sonoma: Views! Stars! Cielo.

Condo rentals with a pool

A three-story building is framed by lush greenery, featuring multiple balconies that overlook the expansive lawn. The architecture includes white railings and gabled roofs, creating a harmonious blend with the surrounding landscape.

4.84 out of 5 average rating, 57 reviews

WorldMark Windsor, CA

A spacious bed is dressed in crisp white linens, featuring a decorative bolster pillow adorned with vibrant floral patterns in shades of green, orange, and brown. A bedside lamp casts a soft glow, highlighting the neutral color of the headboard.

4.67 out of 5 average rating, 9 reviews

Superior Wine Country Condo - 2 Bdm Condo-Sleeps 6

A well-appointed bedroom features a spacious bed dressed in fresh white linens. Two nightstands flank the bed, each with a lamp. A large, decorative wall piece is positioned above the headboard, and a window with blinds allows natural light to enter the room.

Santa Rosa - Self Contained Suite 5 Mins Away

A spacious outdoor pool is surrounded by loungers under shade umbrellas. The adjacent buildings feature balconies and well-maintained greenery. Blue skies and fluffy clouds add to the inviting atmosphere of the resort.

4.5 out of 5 average rating, 4 reviews

2Bdm Condo Windsor WM Resort#4

The exterior of a multi-level resort building is shown, featuring a blend of wood and stucco design. Spacious balconies and porches are visible on upper and lower levels. Lush green lawns surround the property, with pathways leading to the entrance.

5 out of 5 average rating, 5 reviews

Windsor Resort 2bdr Queen

A spacious pool area features a large, clear water swimming pool surrounded by lounge chairs and umbrellas. The adjacent building showcases multiple balconies and staircases, enhancing the inviting atmosphere of the resort.

1 BR Worldmark Windsor Resort Condo Wine Country

A well-appointed bedroom features a spacious bed with a neutral-colored headboard. A decorative pillow rests at the center of the bed. Two bedside tables with lamps are positioned beside the bed, and a window allows natural light to brighten the room.

4.89 out of 5 average rating, 53 reviews

Sip, Taste, Hot Tub - Repeat - 2 Bdrm Condo-Slps 6

A comfortable sofa sits against a light blue wall, adorned with decorative cushions featuring intricate patterns. A small lamp stands beside it, providing ambient lighting. In the background, a well-equipped kitchen is visible, featuring wooden cabinetry and modern appliances.

4.93 out of 5 average rating, 96 reviews

Resort Living w/ Pools - 2 Bdm Condo Slps 6

Other vacation rentals with a pool

An aerial view showcases the expansive property, with a spacious home surrounded by landscaped grounds. A crystal-clear pool is visible adjacent to the house, with lush vineyards and rolling hills in the background, creating a serene natural environment.

4.97 out of 5 average rating, 38 reviews

Tranquil Sonoma Vineyard w/ Pool

The exterior of a mid-century modern home is displayed, featuring a spacious deck adorned with umbrellas and lounge chairs. A heated pool lies in the foreground, surrounded by low landscaping, with the home’s wood and glass structure set against a clear blue sky.

4.96 out of 5 average rating, 24 reviews

Cozy Santa Rosa Home with Scenic Views

4.96 out of 5 average rating, 68 reviews

Guesthouse in Santa Rosa

Guesthouse

4.85 out of 5 average rating, 13 reviews

Three-story buildings are set within a well-maintained lawn. Bushes and trees frame the scene, providing greenery and shade. A clear blue sky is visible in the background, with a few scattered clouds enhancing the tranquil outdoor environment.

Apartment in Windsor

Windsor, CA, 1-bedroom #2

4.98 out of 5 average rating, 95 reviews

The backyard showcases a newly built pool surrounded by a spacious wood deck, featuring in-pool loungers. A picturesque sunset casts warm light on the landscape, while the home and outdoor seating areas are framed by tall trees, creating a serene country atmosphere.

Home in Sebastopol

Sonoma Retreat w/Pool, Hot Tub, Ent Barn + Orchard

5 out of 5 average rating, 6 reviews

NEW! 4Bd Wine Country Vineyard Retreat +Pool +Spa

5 out of 5 average rating, 20 reviews

A white-clad barn-style building features large glass doors on the front, allowing natural light to fill the interior. Wooden decking extends from the entrance, with two wooden chairs positioned for enjoying the outdoor space. Surrounding greenery adds to the inviting setting.

Guesthouse in Healdsburg

Modern Barn Nestled in the Countryside