Vacation rentals with a pool in Windsor

4.88 out of 5 average rating, 105 reviews

The resort's exterior showcases a three-story building with multiple balconies and large windows. Lush green lawns and landscaped gardens surround the building, creating a welcoming outdoor space. Clear blue skies provide a bright backdrop to the well-maintained architecture.

Townhouse in Windsor

Wine and Golf Paradise in Windsor, CA (#1)

The WorldMark-Windsor resort is a timeshare resort located within the Russian River Valley. It is one of California's most beautiful wine regions. The name on the reservation must be the person checking in at the front desk. You must be at least 21 years old to check in. Wifi is available for an additional fee. The resort charges and collects the fee. If your check-in date is on a Friday there may be a delay in getting your room as there is a large volume of guests checking in on Fridays.

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, 102 reviews

5-Bedroom Creekside Wine Country Retreat

Welcome to our spacious and luxurious 5-bedroom, 3-bathroom home in the heart of Sonoma County's Wine Country! With a sparkling pool, relaxing spa, cozy fire pit, and stunning backyard, this impeccably designed home is the perfect vacation home for families or groups of friends looking to experience Wine Country in style. Our Creekside Retreat is located in one of Santa Rosa's most desirable neighborhoods - close to nature and just minutes away from the area's top destinations and attractions.

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.

4.98 out of 5 average rating, 219 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.

4.93 out of 5 average rating, 134 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.

A spacious saltwater pool is surrounded by trees, offering a serene view of the landscape. Ten pool loungers are arranged alongside the pool, while an outdoor dining area is visible in the background, ideal for gathering and enjoying meals.

4.88 out of 5 average rating, 104 reviews

Haven: 5 King Bedrooms, Heated Pool and Hot Tub

This luxury home is perched among the trees with expansive views of wine country. Play on the enormous deck that includes outdoor dining, saltwater pool (gas heated all-year), 10 loungers, and the largest hot tub on the market. Relax in the social kitchen+dining room or large, bi-level living room. Incredible location: Safeway and many restaurants- 5 min, famous wineries in Healdsburg, Kenwood, Glen Ellen - 15-20 min, hiking/biking - 10 min. Everything for an unforgettable vacation!

4.97 out of 5 average rating, 113 reviews

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★

4.89 out of 5 average rating, 248 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.

5.0 out of 5 average rating, 729 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

4.98 out of 5 average rating, 127 reviews

Pool, Hot Tub, Ent Barn, Fire Pit, Apple Orchard

Welcome to Green Hill Retreat. Swim in the solar-heated pool, soak in the 6-person hot tub, or lounge poolside on the spacious wood deck with stunning views of the outdoor space. Stargaze at the dark sky among the apple trees or by the wood fire pit. Head to the entertainment barn for a wet bar, air hockey, big-screen TV projector, darts, and cornhole. The main house features TVs in every room and a new open-concept kitchen. Pet- and family-friendly, EV charging, and fast WiFi.

4.93 out of 5 average rating, 193 reviews

Wine Country Escape: Pool & Hot Tub. Fast WiFi

Escape to our stylish Santa Rosa home, your perfect base for wine country! Comfortably sleeps 8 with 4 bedrooms. Relax in the private backyard oasis featuring a pool, soaking hot tub, and a cozy gas fire pit under a gazebo. Centrally located near world-class wineries, breweries, and dining. Ideal for families and friends seeking a memorable getaway in a quiet, convenient neighborhood. We are happy to help plan your trip or arrange a private wine tasting at the house. Just ask!

4.97 out of 5 average rating, 236 reviews

Wine Country Retreat | Pool, Hot Tub + Vibes

Summer-ready backyard + hot tub | Close to wineries Welcome to Happy House, a comfortable, clean, and welcoming home—perfect for a Sonoma County getaway any time of year. Ideal for wine tasting, visiting local breweries, hiking, mountain biking, plus weekend escapes, or remote work. 🌿 Private Backyard Large yard with pool, hot tub, and easy parking. 🍽 Fully Stocked Chef’s Kitchen 🛋 Seasonal note: Outdoor cushions/umbrellas stored late Oct–mid May. Permit # SVR25-160

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.

4.92 out of 5 average rating, 136 reviews

Private Resort with Pool, Pool House, View and 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.

Popular amenities for Windsor rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.97 out of 5 average rating, 121 reviews

The home is framed by lush greenery and vibrant plants, with a patio featuring outdoor furniture. Warm light spills from the windows, hinting at a cozy interior. A barbecue grill is positioned nearby, providing an inviting space for outdoor gatherings.

Home in Kenwood

Vineyard Haven: Pool, Hot Tub & Wine Country Charm

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.

4.89 out of 5 average rating, 119 reviews

Serene Wine Country Retreat with Pool & Hot Tub

4.98 out of 5 average rating, 137 reviews

Wine Country Retreat- Privacy-Spa/Pool/Games

A modern outdoor area is highlighted by a sparkling pool surrounded by a stone deck. Sun loungers and a large umbrella provide shaded seating, while lush greenery adds a natural backdrop. The home's exterior features clean lines and expansive windows, inviting relaxation.

4.89 out of 5 average rating, 103 reviews

Serene Wine Country Haven with Pool & Hot Tub

4.99 out of 5 average rating, 194 reviews

Home in Guerneville

Modern farmhouse (pool can be heated year round)

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, 215 reviews

Gorgeous Sonoma retreat (with pickleball!)

4.96 out of 5 average rating, 104 reviews

MidCentury Modern Wine Country Private Pool & Spa

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.

4.91 out of 5 average rating, 200 reviews

Historic 1880's Craftsman Style Home with Pool.

Condo rentals with a pool

An inviting common area features high ceilings with exposed beams and ample natural light from large windows. Comfortable leather seating is arranged around wooden tables, while a pool table occupies one corner. A stone fireplace adds warmth to the space, creating a relaxed atmosphere.

4.95 out of 5 average rating, 98 reviews

Great Wine Country and Golfing Resort Getaway!

5.0 out of 5 average rating, 5 reviews

2 Separate 3BR Apts with Resort Amenities

The outdoor pool area is surrounded by lounge chairs and shaded umbrellas, creating a spacious environment for relaxation. Lush greenery borders the pool, while three-story buildings in the background provide additional structure to the inviting setting under a clear blue sky.

4.89 out of 5 average rating, 9 reviews

Windsor, CA, 1 Bedroom #1

An outdoor pool is surrounded by lounge chairs and shaded areas, with a large tree providing a natural focal point. The pool's calm water reflects the soft colors of the sky at dusk, creating a serene atmosphere.

Windsor, CA, 3-Bedroom #1

Windsor Resort @ Russian River Valley-3-Bd Suite

A spacious swimming pool is surrounded by numerous lounge chairs under bright blue skies. Umbrellas provide shade along the poolside area, with well-maintained landscaping adding greenery in the background. The resort buildings are visible, offering a welcoming atmosphere for relaxation.

4.72 out of 5 average rating, 36 reviews

WorldMark Windsor One-Bedroom Condo

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 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

Other vacation rentals with a pool

4.98 out of 5 average rating, 123 reviews

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.

Barn in Santa Rosa

Luxury Wine Country Barn Retreat on 25 Acres

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.

Pony Ranch Vineyard Estate with Pool

4.93 out of 5 average rating, 484 reviews

4.99 out of 5 average rating, 275 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

Pool & garden getaway in beautiful Sonoma Valley!

4.96 out of 5 average rating, 67 reviews

A serene outdoor area features a large pool surrounded by spacious lounge chairs and lush greenery. A hot tub is situated near the pool, with a view of the mountains in the background. The home’s structure is framed by well-maintained landscaping.

Home in Healdsburg

Wine Country Gem | Pool | Hot tub | BBQ

5.0 out of 5 average rating, 8 reviews

Home in Healdsburg

The Grove on Alexander Valley

4.88 out of 5 average rating, 24 reviews

Sonoma Nature Retreat with Heated Pool and Spa

4.95 out of 5 average rating, 22 reviews

The exterior of the resort displays a multi-story building with a traditional architectural style. Soft evening lighting highlights the balconies and entrances, while well-manicured lawns and neatly arranged pathways contribute to the inviting atmosphere.

Apartment in Windsor

Exemplary Windsor 2 Bedroom +Amenities!

Luxe

An outdoor pool area features a heated swimming pool surrounded by sleek lounge chairs. Two large umbrellas provide shade, while a built-in hot tub with a fire pit is situated nearby. Lush greenery and trees create a serene backdrop.