Vacation rentals with outdoor seating in Windsor

4.99 out of 5 average rating, 119 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, 131 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.

5 out of 5 average rating, 110 reviews

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.

Home in Healdsburg

Healdsburg House - Chiquita Road

Relax with the whole family at this peaceful and private home mins to the Healdsburg Square, Montage Resort, and Dry Creek/Alexander Valley Wineries. The updated home features an open concept kitchen, two family rooms, and a sparkling hot tub on 1.5 private acres surrounded by vineyards and oak trees. Cruise your bike to town or head directly out Chiquita Road to some of the world's greatest cycling. 2.4 miles to the Montage Resort. 2.5 miles to the Healdsburg Square. Welcome to Wine Country!

A modern kitchen features a large island with four bar stools, blending navy cabinetry with marble countertops. Bright windows illuminate the space, revealing a glimpse of the outdoor area. An elegant gold sink contrasts with stainless steel appliances and minimalist decor.

4.96 out of 5 average rating, 121 reviews

Botany House Designer Home with Hot Tub

Property is managed by Inspired in Sonoma Discover your Wine Country sanctuary in this lush, design-forward Santa Rosa retreat. With a chef’s kitchen, a six-person hot tub, a fire pit, and Restoration Hardware furnishings, every detail is crafted for comfort and style. Perfectly located near wineries, Michelin-star dining, and redwood adventures, it’s ideal for families or friends seeking luxury and connection. Book your escape today. We are pet-friendly and look forward to hosting you.

4.95 out of 5 average rating, 206 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.

4.92 out of 5 average rating, 126 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.

4.94 out of 5 average rating, 294 reviews

Russian River Brewcation · Wine Retreat

Welcome to the Russian River Brewhouse in the heart of Russian River Valley, one of Sonoma County’s most sought-after wine destinations. Designed for comfort and connection, this inviting retreat is ideal for relaxed evenings, gathering with friends, and experiencing the rhythm of wine country living. Enjoy private, in-home wine tastings brought directly to you—no driving or reservations required. Your stay includes access to curated tasting experiences at select local wineries.

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, 135 reviews

WineCamp - Russian River Valley AVA - No Pets

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 covered terrace and vineyards beyond. This wine and beer themed property is not suitable for children.

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, 160 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.

4.97 out of 5 average rating, 674 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, 437 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.

4.81 out of 5 average rating, 153 reviews

A spacious dining area features a rustic wooden table set for eight, surrounded by leather-tacked chairs. Nearby, a well-equipped kitchen is visible, showcasing wooden cabinetry and modern appliances. Natural light fills the room, complemented by greenery from potted plants in the background.

Home in Windsor

Healdsburg Winemaker’s Wine Country Gem

Welcome to our 6-bedroom retreat, owned by a passionate Healdsburg winemaker, located in the heart of Windsor. This home is the perfect getaway for families, groups, or wine lovers looking to immerse themselves in the charm of Wine Country. Inside, each bedroom offering crisp linens, plush pillows, and soft lighting for ultimate relaxation. After a day of exploring the wineries, unwind in the private hot tub, where you can soak your cares away in style.

Popular amenities for Windsor outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

5 out of 5 average rating, 106 reviews

Home in Sebastopol

Pixel Place - A Private Arcade + Outdoor Sanctuary

4.95 out of 5 average rating, 169 reviews

An outdoor space features a plunge pool surrounded by a sun deck with lounge chairs and a sun umbrella. The home, with its wood accents, is set against a backdrop of tall redwood trees, contributing to a serene, natural setting.

Home in Occidental

Modern mid-century-inspired, Deer Ranch

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, 102 reviews

Wine Country Villa Heated Pool Hot Tub Upper Level

4.95 out of 5 average rating, 307 reviews

A spacious deck features a hot tub surrounded by vibrant greenery and comfortable outdoor chairs. Views of the vineyard and rolling hills are visible in the background under a clear blue sky.

Home in Sebastopol

Sonoma County Historical Ranch House on a Vineyard

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, 169 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, 143 reviews

Amazing Santa Rosa Wine Escape Home

4.96 out of 5 average rating, 197 reviews

Home in Forestville

Hilltop Wellness Retreat | Sauna + Hot Tub

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, 108 reviews

Centrally Located Modern Wine Country Home

Apartment rentals with outdoor seating

4.97 out of 5 average rating, 873 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, 500 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, 753 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, 272 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, 230 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, 522 reviews

Apartment in Petaluma

Central charming studio w/pvt patio + breakfast

4.96 out of 5 average rating, 366 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

Victorian Garden Apartment - walk to downtown

Condo rentals with outdoor seating

A circular swimming pool is surrounded by lounge chairs, offering a spacious area for relaxation. Lush greenery and buildings are visible in the background, while the sky displays soft hues of pink and blue, indicating a serene evening ambiance.

Windsor, CA, Studio Z #1

4.99 out of 5 average rating, 114 reviews

A private patio features a swinging egg chair, capable of seating at least two people, surrounded by lush bamboo and a grassy area. Outdoor lights can be seen, complementing the serene atmosphere, while a pyramid heater provides warmth for cooler evenings.

Condo in Napa

Spacious&PeacefulOasis!Beautiful!PerfectlyLocated!

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

The outdoor pool area features a circular pool surrounded by a spacious deck. Several lounge chairs are positioned around the pool, offering seating options. A large tree provides shade nearby, and a building with patio seating is visible in the background.

Windsor, CA, Studio Z #2

5 out of 5 average rating, 4 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

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.