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, 141 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, 170 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.

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, 461 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

The villa stands nestled among the trees, featuring a spacious driveway leading to a tri-garage. Its exterior combines warm tones with charming shutters. The picturesque hillside setting offers a blend of greenery and distant trees, contributing to a serene ambiance.

4.92 out of 5 average rating, 105 reviews

Wine Country Opulent Villa-Brush Creek

Welcome to Brush Creek, a 20-minute drive from Sonoma, Napa, Russian River, Alexander, and Knight's Valleys. Our cozy villa offers five unique bedrooms, including a regal King Master suite. Complimentary EV charging. Healdsburg, Calistoga, and the trendy Barlow are easily accessible. Our attentive staff handles all the chores while you can enjoy the complimentary gourmet coffee. Brush Creek: where comfort, luxury, and character converge for an unforgettable wine country retreat. SVR25-100

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, 109 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, 677 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, 186 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.

A Mediterranean-inspired house is set amidst lush gardens and rolling hills. The round swimming pool is surrounded by colorful landscaping and lounge chairs, inviting relaxation. The exterior features warm stucco walls and a tiled roof, showcasing a harmonious blend with the natural surroundings.

5 out of 5 average rating, 119 reviews

Wine Country Luxury Retreat - Pool Sauna Spa Views

Welcome to Sonoma Valley Retreat! The Luxury Mediterranean-inspired resort style house in the middle of a world-class wine country. 3600 Square feet House is located in the world-famous Sonoma Valley and is perfect for all your vacation needs. It's where style and sophistication meets entertainment and fun. Enjoy stunning outdoor amenities; one of a kind round soaking pool private pool with spa, pine wood sauna and breathtaking garden, mountain views

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

Popular amenities for Windsor rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.84 out of 5 average rating, 103 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

4.97 out of 5 average rating, 101 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!

The serene pool area is surrounded by lush greenery, featuring modern lounge chairs and large umbrellas for shade. The sparkling water invites relaxation, while a covered outdoor space extends from the home, providing a seamless transition to the tranquil outdoor retreat.

4.88 out of 5 average rating, 111 reviews

Serene Wine Country Retreat with Pool & Hot Tub

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.

4.91 out of 5 average rating, 120 reviews

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

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.

4.98 out of 5 average rating, 186 reviews

Sebastopol Gem, The Birdhouse. Hottub. Pool. Views

4.86 out of 5 average rating, 117 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

4.75 out of 5 average rating, 239 reviews

An outdoor deck features multiple dining tables with striped place settings, overlooking lush greenery. The wooden flooring extends towards the edge, providing a spacious area for relaxation. Large glass doors lead back into the home, inviting natural light into the space.

Home in Guerneville

SoLEIL OPEN Friendsgiving! Cook's Kitchen+Hot Tub

A private outdoor area showcases a heated pool surrounded by a spacious deck. Lounge chairs are positioned for relaxation, and white umbrellas offer shade. Lush greenery and trees create a serene backdrop, enhancing the inviting and open atmosphere.

4.94 out of 5 average rating, 187 reviews

Gorgeous Sonoma retreat (with pickleball!)

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

An expansive outdoor swimming pool is surrounded by comfortable lounge chairs and shaded umbrellas. The well-maintained area features lush greenery and light blue skies. Adjacent buildings provide a backdrop, showcasing multiple balconies and patios.

4.78 out of 5 average rating, 9 reviews

WM Windsor 3 Bedroom Condo

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

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

The image shows a resort with multi-story buildings surrounding a swimming pool. A spacious pool area is depicted, featuring lounge chairs arranged near the water and umbrellas providing shade. Clear blue skies are visible above, enhancing the resort's inviting appearance.

5 out of 5 average rating, 10 reviews

3bdm-condo Windsor-WorldMark Resort

A well-equipped kitchen and dining area are featured, showcasing wooden cabinetry and a large dining table set for six. Modern appliances include a refrigerator, stove, and microwave. Natural light floods the space through a window, creating a bright and functional atmosphere.

4.83 out of 5 average rating, 47 reviews

LAST MINUTE PRICE - 2 Bdrm Condo - No Cleaning Fee

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

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, 37 reviews

Tranquil Sonoma Vineyard w/ Pool

4.95 out of 5 average rating, 66 reviews

Guesthouse in Santa Rosa

Guesthouse

An expansive backyard is shown, featuring a sparkling pool surrounded by a stone patio. A gazebo offers shaded seating, while a cozy fire pit creates an inviting gathering space. Lush greenery and trees frame the scene, enhancing the tranquil setting of the home.

4.96 out of 5 average rating, 77 reviews

5-Bedroom Creekside Wine Country Retreat

5 out of 5 average rating, 4 reviews

Home in Glen Ellen

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

5 out of 5 average rating, 17 reviews

An outdoor space features a heated inground pool with a spa area, surrounded by a sleek stone deck. Lush greenery and trees enhance the privacy and tranquility. A fence encloses the area, ensuring a safe environment for guests to enjoy.

Home in Healdsburg

Healdsburg Modern Sleeps 8, pool, spa, firepit

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

4.67 out of 5 average rating, 6 reviews

Chic Mid-Century Home | Pool + Hot Tub