Vacation rentals with outdoor seating in Windsor

4.99 out of 5 average rating, 125 reviews

A covered patio is framed by wooden beams, offering a view of expansive vineyard landscapes and distant hills. Outdoor seating, including a dining table and lounge chairs, is arranged on the deck, inviting relaxation amid the tranquil scenery.

Guesthouse in Healdsburg

Bucher Vineyard Cottage

Discover the Charm of Our Vineyard Cottage! Escape to the heart of wine country with a stay at our fantastic one-bedroom cottage, nestled on the renowned Bucher Vineyard. Large room with kitchen & cozy seating area. Enjoy a restful night in a comfy queen bed surrounded by a stunning Redwood wall. Covered patio with heaters and fan. Deck with spectacular views of our vineyard & the Russian River Valley. Gas fire pit near deck. Hosts John & Diane are farmers and winery owners live on the property.

4.99 out of 5 average rating, 132 reviews

The exterior of a charming Victorian house is visible, featuring a welcoming front porch with a green door. Lush greenery and colorful plants frame the entrance, and a rustic wooden cart is placed nearby on a gravel pathway, enhancing the inviting outdoor space.

Home in Windsor

Gorgeous Victorian in the HEART of Windsor

Gorgeous renovated Queen Anne Victorian located in the heart of Windsor, CA combines quality finishes, modern convenience & vintage details. With a stylish kitchen, high ceilings, 3 beds/2 baths on a single level, HVAC & a huge lot with a Bocce Court. Walking distance to the Town Green, restaurants, wine tasting rooms and shopping. Just 3.5 miles from the Sonoma County Airport (STS), 5 miles to downtown Healdsburg, in the heart of the Russian River Valley & just 57 miles from the Golden Gate.

An expansive outdoor patio area features modern metal furniture and a covered dining table, inviting al fresco meals. Large sliding glass doors create a seamless flow between indoor and outdoor spaces, with a view of the surrounding natural landscape and vineyard beyond.

4.97 out of 5 average rating, 139 reviews

WineCamp - Wine Country - Vineyard View Hot Tub

The WineCamp concept is rooted in the rural ambience of working local vineyards and craft breweries. This purpose-built residence offers indoor/outdoor living at it best. Conceived as the ideal space for two adult couples, the spacious dual master suites are separated by gracious open-plan living areas that flow seamlessly through multi-panel sliding walls of glass onto the terrace with Sundance spa hot tub and vineyards beyond. This wine and beer themed property is not suitable for children.

A modern living area showcases a comfortable gray sectional sofa and two accent chairs. A round wooden coffee table sits in the center, with a small plant adding a touch of greenery. Soft lighting is provided by a ceiling fixture and table lamps, enhancing the inviting atmosphere.

4.92 out of 5 average rating, 144 reviews

Healdsburg 2br Cottage with Private Yard!

Relax at our renovated private guesthouse a 5 min drive (1 mi) from the Healdsburg Plaza. Updated 2 br/ 1 ba home with private yard and outdoor dining and lounge areas. Our layout is ideal for one family or close friends traveling together as the one bathroom is accessed through the primary bedroom. Perfect for a wine country getaway- convenient location just outside of Healdsburg city limits in a vineyard adjacent neighborhood. We love kids and welcome them! Permit #TVR22-0119

4.93 out of 5 average rating, 646 reviews

Healdsburg Garden House

June Sale! Clean, Cozy & Private 3BR Retreat Near Healdsburg Town Square Enjoy this 3-bedroom, 2-bath home, an ideal base for Sonoma wine country. Covered redwood deck with gas grill, plus 50” HDTVs and fast 1 GB Wi-Fi. Fully stocked kitchen w/ dishwasher. New A/C and heating. 1 mile from Healdsburg Town Square, close to wineries, dining, and shops. Russian River beach nearby for outdoor activities. Perfect for families, couples, or small groups seeking a private getaway. TOT #798N

4.95 out of 5 average rating, 212 reviews

A wooden bridge connects the ground to a treehouse elevated among tall trees. The treehouse features large windows and a circular design, surrounded by lush greenery. A sturdy netting lines the sides of the walkway, ensuring safety while traversing to this unique retreat.

Treehouse in Bodega Bay

Eagle's Nest Treehouse Farm Stay

Eagle's Nest Treehouse Farm Stay is a tranquil, secluded, luxurious, romantic wilderness experience in a private forest on a 400 acre working ranch. Thirty feet above the forest floor you are nestled in a gorgeous, well-appointed suite of 1,000 year old polished redwood, with bathroom and amazing copper/glass forest-view shower. Explore hiking trails through the forest and learn about ranch operations (Highland cattle, goats and ducks). See guest comments in the space description.

The exterior showcases a landscaped garden featuring diverse greenery, decorative rocks, and a serene stone pathway. A gazebo is positioned in the garden, complementing the house’s two stories, which are framed by trees and plants. The scene is illuminated by soft natural light.

4.97 out of 5 average rating, 227 reviews

Elegant & Spacious Luxury Wine Country Estate

The perfect place for your group to stay in Wine Country! Featuring two large entertaining areas and an additional dining room, this is a great place for fun and relaxation! Play ping pong, pool or poker in our game room, or dine on our spacious patio under the pergola! Relax and soak in our hot tub and enjoy the zen gardens and tranquil water feature, or sip on a glass of wine by the outdoor fire pit. Close to the Sonoma County Airport, wineries, and world-class dining. Welcome home!

A light-filled living area features a sectional sofa, coffee table, and a flat-screen television mounted on the wall. Large windows provide sweeping views of the surrounding vineyards and natural light. A patterned area rug complements the wood flooring, enhancing the cozy atmosphere.

5 out of 5 average rating, 166 reviews

VINEYARD VIEW - Beautiful 3 bed/2 bath, Santa Rosa

Enjoy beautiful unobstructed vineyard views from your own private patio while sipping coffee or a glass of wine. This beautifully decorated new home is located in a quiet peaceful neighborhood in N. Santa Rosa in the heart of wine country with several wineries and breweries nearby. We are located only 5 miles from downtown Santa Rosa, 12 miles from the Healdsburg plaza, and 45 miles from Napa. This one-story home is perfect for enjoying all that Sonoma County has to offer.

The living room features a leather sofa and loveseat, accompanied by an end chair. A coffee table sits in the center, and a wall-mounted TV is positioned above a gas fireplace. Large windows and sliding doors provide views of the outdoor area.

4.94 out of 5 average rating, 256 reviews

Winemaker's Delight: 3BD/3BA Russian River Valley

A stylish 3-bedroom vacation rental in the heart of Santa Rosa, owned by passionate winemakers and perfectly located near top Sonoma wineries, tasting rooms, restaurants, and scenic drives. Ideal for up to six guests, this beautifully designed Wine Country retreat features inviting living spaces and three thoughtfully styled bedrooms with plush linens and serene décor, creating the perfect home base for relaxing, exploring, and enjoying the best of Sonoma County.

4.97 out of 5 average rating, 682 reviews

The exterior of a rustic winery building is featured, characterized by its earthy tones and distinctive red door accents. Lush greenery and blooming purple flowers surround the structure, enhancing its natural setting. The building's design includes terracotta roofing and large windows that invite an abundance of natural light.

Farm stay in Healdsburg

Gracianna Winery Vineyard Loft - Farm Stay

Costs vary based on availability. Luxury estate loft in Gracianna Winery's vineyard on Westside Road's Miracle Mile of Pinot Noir in Healdsburg includes equipped kitchen with new gas Wolf Range. Pick up breakfast needs before arriving. Vineyard machines may work overnight with lights & disruptive noises, especially during the summer and harvest is in late August early Sept. TASTING ROOM CLOSED DECEMBER 1 - MARCH 31. LOFT AVAILABLE YEAR ROUND. TOT #3294N

4.96 out of 5 average rating, 439 reviews

A spacious living area features a blue sofa adorned with a soft orange throw. A large area rug with intricate patterns anchors the space, while natural light floods in through large windows. A wooden coffee table rests centrally, complemented by decorative items.

Home in Windsor

Winelight Vineyard Home With Spa

Gated driveway, private, scenic, safe, secure, and impeccably clean. Unwind, prepare dinner on granite counter tops in this newly remodeled well-stocked gourmet kitchen. Enjoy plush amenities, fine decor, hot tub, romantic fireplace, French doors leading to outdoor decks, secluded rural vibe, reliably fast internet. Close to Sonoma County's best wineries, breweries and restaurants. There is a guest laundry, designer carport, and ample parking for guests.

4.97 out of 5 average rating, 617 reviews

A rustic cabin is nestled among towering redwood trees, featuring wooden shingles and large windows. A wooden deck, adorned with string lights, enhances the inviting exterior, while the natural landscape provides a serene backdrop. A gravel path leads to the entrance.

Cabin in Occidental

Rustic Yet Luxurious Cabin in the Redwoods

This rustic yet luxurious cabin is the perfect place to unplug. Walk through the woods, relax by a fire, and enjoy the food and wine of the Russian River Valley. 10 minutes from the beach. Minutes from Occidental, Graton, Forestville, and Guerneville. House has a full bathroom, bedroom downstairs with a Cal King bed and one upstairs with two twin beds. 5 acres in the redwoods, trampoline, fire pit area, high-speed Internet.

Popular amenities for Windsor outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

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.

4.92 out of 5 average rating, 130 reviews

Vineyard Vista, Modern Farmhouse Cottage with Pool

4.96 out of 5 average rating, 105 reviews

An open-concept kitchen and dining area features a large wooden dining table and modern kitchen appliances. A spacious island with bar seating is included, and the bi-fold patio doors lead to a deck with lounge seating surrounded by greenery.

Home in Forestville

Russian River Luxury Escape | Private Hot Tub

An inviting living area features a large black sectional sofa complemented by a wooden coffee table atop a light area rug. Natural light streams through large windows adorned with sheer curtains, illuminating traditional wood accents and hardwood floors.

4.95 out of 5 average rating, 691 reviews

Craftsman 2 blocks from Russian River Brewery!

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, 103 reviews

Wine Country Villa Heated Pool Hot Tub Upper Level

An airy living space is highlighted by high-beamed ceilings and large windows, allowing plenty of natural light. A gray sofa and two brown leather chairs are arranged around a round coffee table on a light-colored rug. The adjacent dining area features a wooden table, surrounded by various chairs.

5 out of 5 average rating, 114 reviews

Healdsburg House - Chiquita Road

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.

4.94 out of 5 average rating, 175 reviews

Wine Country Escape: Pool & Hot Tub. Fast WiFi

A spacious bedroom features a comfortable bed with soft linens and a decorative throw blanket. Nightstands flank the bed, with lamps providing a warm glow. A large window allows natural light, while a chest of drawers offers storage. A potted plant adds a touch of greenery.

4.95 out of 5 average rating, 148 reviews

Amazing Santa Rosa Wine Escape Home

A well-appointed bedroom features a spacious bed with a light-colored upholstered headboard, draped in soft linens and a textured throw. Two nightstands flank the bed, each with a lamp and decorative items. Large windows allow natural light to illuminate the room, while soft curtains frame the view.

4.94 out of 5 average rating, 113 reviews

Centrally Located Modern Wine Country Home

Apartment rentals with outdoor seating

4.97 out of 5 average rating, 882 reviews

A hand-painted welcome sign is displayed on a white oval background. Red cursive lettering spells 'Welcome,' surrounded by colorful flowers and green leaves, creating an inviting entry point.

Apartment in Santa Rosa

Private Getaway in West Santa Rosa

4.97 out of 5 average rating, 508 reviews

A round table with two chairs is positioned on lush green grass, overlooking a misty landscape at sunrise. The fog blankets the valley, enhancing views of rolling hills and distant trees. A potted plant adorns the table, creating a serene outdoor dining space.

Apartment in Penngrove

Valley View-Sonoma Mountain Terrace

4.99 out of 5 average rating, 762 reviews

A modern studio space features a spacious layout with a queen bed and a desk area. Natural light streams in through skylights and a window, highlighting the warm wood tones of the cabinetry and furniture. A cozy seating area includes a round table and an ergonomic chair.

Apartment in Sebastopol

Amy's Local BNB - walk to town **and hot tub!**

4.99 out of 5 average rating, 179 reviews

A comfortable seating area features a spacious sofa and two high-backed chairs, accompanied by a coffee table on a light rug. Natural light enters through large windows covered with woven shades, enhancing the relaxed ambiance of the space.

Apartment in Sonoma

2 bedroom Apartment with Balcony Downtown Sonoma

4.93 out of 5 average rating, 274 reviews

The loft features a cozy sleeping area with a spacious bed dressed in decorative linens. A small dining table is positioned nearby, complemented by a lamp and artwork on the walls. Natural light enters through a skylight, enhancing the inviting atmosphere.

Apartment in Sonoma

Lily's Loft

4.91 out of 5 average rating, 233 reviews

A covered outdoor space is framed by wooden beams and features a gravel floor. A rectangular table is surrounded by several chairs, with a bright green lounge chair visible in the background. A decorative sign reading 'HELLO WINTER' hangs on the fence.

Apartment in Santa Rosa

Sonoma County Getaway: Mins to Wineries & Downtown

4.98 out of 5 average rating, 203 reviews

A vibrant street scene features a stone building with a distinct architectural style, framed by lush greenery and palm trees. Vehicles line the road, suggesting a lively atmosphere. Rolling hills are visible in the background, adding depth to the landscape.

Apartment in Sonoma

Above and On Broadway - MaryJean’s Place

4.96 out of 5 average rating, 369 reviews

The exterior of a Victorian home is surrounded by vibrant greenery, featuring a white picket fence and colorful shrubs. A pathway leads to the entrance, with large windows adorning the house, highlighting its charming architectural details.

Apartment in Petaluma

Cozy Petaluma Apt Walk to Dining & Downtown Shops!

Condo rentals with outdoor seating

WorldMark Windsor Three-Bedroom Condo

An outdoor pool is surrounded by lounge chairs, offering a space for relaxation. Trees and buildings frame the area, with a gentle sky reflecting soft colors in the water. The spacious pool invites guests to enjoy outdoor leisure.

Windsor, CA, 2-Bedrm SN #1

5 out of 5 average rating, 5 reviews

2 Separate 3BR Apts with Resort Amenities

An outdoor pool area is captured under clear blue skies, featuring a curvy, inviting pool with a light blue surface. Surrounding the pool are multiple lounge chairs arranged neatly, and well-kept landscaping provides a lush backdrop. A clubhouse can be seen in the distance.

Professionally Managed 2BR Condo, Pool & BBQ

Windsor, CA, 2-Bdr Queen Z #1

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

An outdoor pool area is surrounded by lounge chairs, inviting relaxation. Lush greenery and buildings encircle the pool, creating a serene environment. The sky displays soft hues as the sun sets, reflecting on the still water, enhancing the peaceful ambiance of the resort.

Windsor, CA, 2-Bdrm Twin #1

An outdoor pool is surrounded by lounge chairs, inviting relaxation under a partly cloudy sky. The pool's calm water reflects the surrounding buildings and greenery, creating a tranquil atmosphere. Sun umbrellas provide shaded seating areas beside the pool.