Vacation rentals with a pool in Windsor

Guest suite in Santa Rosa

A shaded outdoor lounging area is framed by vibrant orange flowers, featuring a covered seating arrangement surrounding a central table. The stone-accented pool reflects the natural greenery, creating a serene environment for relaxation.

4.99 out of 5 average rating, 191 reviews

Wine Country Retreat w Pool & Spa-1 Acre Grounds

This one-acre estate offers the quiet and convenience of beautiful Bennett Valley. Just a short drive to the east you will find beautiful vineyards, wine tasting, and farm-fresh cuisine in Sonoma Valley. North 20 minutes up hwy 101 you will find spectacular vineyards in Alexander Valley, Dry Creek Valley, as well as elegant tasting rooms and shops in the town of Healdsburg. Located minutes from shopping and local sites, but you will feel worlds away in an upscale, quiet, peaceful neighborhood.

4.98 out of 5 average rating, 175 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

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

Cozy private 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

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

4.91 out of 5 average rating, 136 reviews

A serene pool area is illuminated by soft landscape lighting, surrounded by lush greenery. A hot tub is positioned nearby, and a stylish lounge chair complements the outdoor setting. The sky displays vibrant hues of orange and pink, signaling a tranquil sunset.

Home in Sebastopol

The Deer Retreat – Privacy and Comfort

At the end of a private road (recently redone), the Deer Retreat offers privacy to enjoy the newly renovated pool, the hot tub, and the full outdoor kitchen. With sprawling views of a large private backyard, you will be sure to spot some deers or wild turkeys who call this peaceful place home. When staying inside, you will enjoy the privacy of the 2 large en-suite master bedrooms which are located at opposite ends of the house, or regroup in the large vaulted living room with open kitchen.

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, 111 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, 682 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

4.9 out of 5 average rating, 210 reviews

A spacious outdoor space features a shimmering pool surrounded by wooden decking. A covered seating area with comfortable furniture is visible nearby, alongside a barbeque setup. Lush greenery encompasses the area, creating a tranquil retreat. A water slide adjoins the pool for added fun.

Guesthouse in Santa Rosa

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.

4.87 out of 5 average rating, 188 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, 211 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

5 out of 5 average rating, 158 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

4.91 out of 5 average rating, 197 reviews

A beautifully landscaped garden features a pathway bordered by gravel and decorative plants. White wicker chairs surround a small table, inviting relaxation. The wooden deck and spa pool are visible in the background, complementing the modern home adorned with solar panels.

Home in Glen Ellen

Luxury home, hot tub/spa pool, walk to restaurants

A relaxing outdoor space features a sunny pool area surrounded by palm trees. Two loungers with bright cushions are positioned beside the pool, which reflects the blue sky. An umbrella provides shade nearby, completing this inviting retreat in a tropical setting.

4.86 out of 5 average rating, 132 reviews

Tropical Oasis with Pool & Hot Tub 30min to Sonoma

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.

4.97 out of 5 average rating, 100 reviews

An aerial view reveals a modern log cabin surrounded by lush greenery, showcasing a spacious pool and inviting spa. Blue lounge chairs line the pool's edge, and the property features ample outdoor space bordered by trees, enhancing the sense of privacy.

Home in Guerneville

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

4.85 out of 5 average rating, 106 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, 182 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, 142 reviews

A well-maintained pool area is showcased, with clear water reflecting the blue sky. Surrounding the pool, a spacious deck is visible with outdoor furniture and access to a raised deck. Lush trees provide natural shade to the area.

Home in Petaluma

Nice Wine Country Family Home

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

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

Superhost

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.

4.7 out of 5 average rating, 10 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

Superhost

A well-lit bedroom features a spacious bed with a neutral-colored headboard and white linens. Bedside tables with lamps are positioned on either side. A window with sheer curtains allows natural light to fill the room, creating a serene atmosphere.

4.76 out of 5 average rating, 58 reviews

Resort Amenities Near Top Food & Wine - Slp 6

The master bedroom features a spacious king bed dressed in white linens, complemented by a decorative throw pillow. Two bedside tables with lamps are positioned on either side. Natural light enters through a window with blinds, enhancing the room's calming atmosphere.

4.82 out of 5 average rating, 34 reviews

Wine Country 2 Bdrm Condo w/ Pools & Hot Tubs

A spacious bed is adorned with multiple soft, white pillows and a decorative bolster pillow featuring a vibrant floral pattern. A bedside lamp emits a warm glow, providing a cozy ambiance to the sleeping area.

4.91 out of 5 average rating, 54 reviews

Make This Your Best Vacation Ever - 2 Bdrm Condo

Other vacation rentals with a pool

Superhost

The image captures the exterior of the farm house at sunset, featuring a newly installed in-ground pool highlighted by sun rays. Two lounge chairs are positioned near the pool, surrounded by landscaped gardens and serene greenery, with the backdrop of the charming house and towering trees.

Home in Healdsburg

4.81 out of 5 average rating, 27 reviews

Eastside Eden | Wine Tastings Included

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

The exterior of a beautifully designed house is presented, showcasing a light-colored facade with decorative shutters and a newly paved pathway. A stone fountain serves as a focal point amidst landscaped greenery, highlighting the inviting entrance and two stories of windows.

4.97 out of 5 average rating, 88 reviews

Wine County Opulent Villa Pool/Hot Tub-Upper Level

4.95 out of 5 average rating, 60 reviews

A comfortable living space is highlighted by a cozy sofa with decorative cushions and an accent chair featuring a circular pattern. A wooden coffee table sits in the center, complemented by a flat-screen TV and a modern electric fireplace set against a textured wall.

Apartment in Windsor

Sonoma Windsor Wine Country 2 bedroom Sleeps 6!

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

4.97 out of 5 average rating, 64 reviews

Home in Healdsburg

Wine Country Estate: Pool, Spa & Vineyard Views

4.88 out of 5 average rating, 59 reviews

A well-appointed sleeping area features a four-poster bed dressed with a floral duvet. Two bedside lamps flank the bed, providing soft lighting. A small wooden table and chair are situated to one side, with light filtering in from sheer curtains framing the window.

Home in Windsor

Adventures surround this charming 2bedroom home.

The image showcases the Quail Roost property, featuring a spacious outdoor deck with a fire pit and pool. The interior highlights a cozy seating area with artful touches, large windows providing natural light, and elegant furnishings. The exterior view captures the pool and surrounding scenic landscape.