Holiday rentals with outdoor seating in Windsor

Guest house in Healdsburg

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.

4.99 out of 5 average rating, 106 reviews

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, 125 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.

Guest house in Santa Rosa

The studio cottage features a balanced layout with a queen bed highlighted by wooden furnishings. A small desk and an ergonomic chair are positioned near a wall-mounted television. Natural light illuminates the space through two windows, creating a comfortable environment.

4.89 out of 5 average rating, 1,200 reviews

Clean Comfy Cottage Downtown

Our tree shaded studio cottage is one block from the heart of downtown. Stay just a two block walk from Russian River Brewing. This clean and quiet cottage has a full kitchen, a comfortable queen bed. I am happy to customize the space to your needs. I offer soft and firm mattresses. I use cotton blankets so that you can have any weight on your bed that you would like. You are welcome to stack seven or more blankets at a time. I will adjust my cleaning regimen to meet your preferences.

Guest suite in Santa Rosa

A spacious private deck is seen with views overlooking the rolling hills and valleys. Comfortable green lounge chairs are positioned for relaxation. The deck features wooden railing and steps leading down, while a doorway connects to the guest suite.

4.96 out of 5 average rating, 363 reviews

Wikiup lookout retreat

We self-developed our rural property as a secluded retreat with dog-friendly gardens. To share our creation with you, we designed a private 2nd-floor guest suite (ok to bring your good dogs). Your suite includes secure parking, private entrance, deck, kitchen, dining, living, 3 beds (queen, double, twin), one bath & a fenced back yard. We are on a country road near Healdsburg, Windsor, Russian River, Sebastopol, Santa Rosa, Calistoga, Sonoma & Napa valleys, wineries & beaches.

5 out of 5 average rating, 690 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

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, 129 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, 156 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.

Guest suite in Junior College

A cozy guest suite features a queen-size bed with a textured blanket and decorative pillows. A small desk with a chair and a mini fridge are positioned nearby. Soft lighting and wall art enhance the ambiance, while a ceiling fan provides comfort.

4.94 out of 5 average rating, 234 reviews

Cozy Private Guest Suite Centrally Located

This recently remodeled guest suite in Santa Rosa’s Junior College neighborhood offers a cozy retreat for 1-2 guests. It features a queen-size bed with a natural latex mattress, Smart TV, WiFi, mini fridge, microwave, Keurig coffee maker, and electric kettle. Relax in the shared garden courtyard with Adirondack chairs, a bistro table, and a propane grill. On-street parking is plentiful, and with a Walk Score of 85, you’re close to shops, dining, and the college.

4.97 out of 5 average rating, 653 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, 434 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.

5 out of 5 average rating, 218 reviews

A hot tub is positioned on a grassy area, offering a view of rows of grapevines against a serene sunset. Colorful flowers are visible nearby, complementing the natural surroundings.

Home in Healdsburg

10-Acre Vineyard Cottage w/Hot Tub + Bocce Court

Escape to a private and peaceful retreat surrounded by Russian River Valley Chardonnay and olive trees. Set on 10 acres of producing vines, our cottage offers vineyard views, a bocce court, fire pit, garden, cruiser bikes, and a sparkling hot tub. Immerse yourself in world-class food, wine, cycling, and nature. Guests staying 3+ nights will receive a complimentary bottle of Chardonnay crafted from our vines. Your perfect wine country escape awaits!

Place to stay in Sebastopol

A spacious room features a large arched window that frames scenic views of the surrounding vineyards. A freestanding soaking tub is positioned nearby, while a private deck is accessed through sliding glass doors. A person stands on the deck, enjoying the fresh air.

4.99 out of 5 average rating, 171 reviews

The Sonoma Spyglass | Incredible Views + Sauna

The Sonoma Spyglass is a gorgeous 600 sqft retreat, designed and built by Artistree Homes, seamlessly blending sustainability with a deep connection to nature. Tucked in the heart of Sonoma’s wine country, this unique gem offers access to nearby walks and local wineries, making it perfect for couples or solo travelers. Soak in the tub with incredible views or enjoy the detached barrel sauna for a perfectly relaxing stay.

Popular amenities for outdoor seating rentals in Windsor

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.97 out of 5 average rating, 204 reviews

A bright living area features a unique circular fireplace with a dark metal chimney as the focal point. Large windows allow natural light to fill the space, highlighting a wooden ceiling and floor. A cozy seating arrangement includes a modern leather chair and a wooden coffee table.

Home in Jenner

Pelican Hill House

The kitchen features warm wooden cabinetry and an expansive central island. Stainless steel appliances include a refrigerator and microwave. Pendant lights illuminate the space, while natural light streams through a nearby window. Bar stools provide seating at the island, enhancing a functional cooking area.

5 out of 5 average rating, 181 reviews

Casa de Gamay - Your Home Away From Home

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.

4.97 out of 5 average rating, 117 reviews

Sustainable Luxury Barn - Secluded Sonoma Retreat!

4.92 out of 5 average rating, 121 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

4.96 out of 5 average rating, 432 reviews

A view of the open living area reveals a cozy sofa adorned with colorful cushions. A wooden dining table is situated nearby, accompanied by simple wooden chairs. A large artwork of sunflowers adds a touch of character, while a decorative coffee table holds potted plants and flowers.

Home in Sebastopol

Sebastopol Guest House

A single-story granny unit is presented with a beige exterior and a red door. Two windows flank the entrance, allowing natural light into the space. A small patio area with a table and chairs is visible to the side, surrounded by landscaping that adds privacy.

4.88 out of 5 average rating, 298 reviews

Sunshine cottage

4.89 out of 5 average rating, 405 reviews

The bedroom features a spacious bed with white linens accentuated by a decorative pillow. A ceiling fan is present, and natural light enters through a window. Artwork adorns the walls, including a map and framed prints. A small desk and a television stand complete the space.

Home in Healdsburg

Wine Country Cottage in Healdsburg

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.

4.93 out of 5 average rating, 101 reviews

Centrally Located Modern Wine Country Home

Apartment rentals with outdoor seating

4.97 out of 5 average rating, 862 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.

Flat in Santa Rosa

Private Getaway in West Santa Rosa

4.97 out of 5 average rating, 486 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.

Flat in Penngrove

Valley View-Sonoma Mountain Terrace

4.99 out of 5 average rating, 741 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.

Flat in Sebastopol

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

4.99 out of 5 average rating, 177 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.

Flat in Sonoma

2 bedroom Apartment with Balcony Downtown Sonoma

4.93 out of 5 average rating, 269 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.

Flat in Sonoma

Lily's Loft

4.91 out of 5 average rating, 225 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.

Flat in Santa Rosa

Sonoma County Getaway: Mins to Wineries & Downtown

4.97 out of 5 average rating, 194 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.

Flat in Sonoma

Above and On Broadway - MaryJean’s Place

4.98 out of 5 average rating, 512 reviews

A studio apartment features a queen bed with white bedding against a vibrant blue wall. A cozy seating area includes two armchairs and a coffee table. Decorative accents are present, with a sliding barn door leading to a stylish bathroom visible in the background.

Flat in Petaluma

Central charming studio w/pvt patio + breakfast

Apartment rentals with outdoor seating

A spacious outdoor pool is surrounded by lounge chairs and shaded by trees. Clear water reflects the sky, and a calming atmosphere is created by the overall layout. Nearby, buildings provide access to the pool area, enhancing the resort-like feel.

Windsor, CA, Studio #2

An inviting pool area is featured, surrounded by sun loungers arranged around the circular shape. Lush greenery and several multi-story buildings are visible in the background, with a sunset sky adding a soft hue to the scene.

Windsor, CA, 1-Bedrm SN #2

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

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

A circular outdoor pool is framed by a mixture of lounge chairs and shaded areas, surrounded by greenery and resort buildings. The water reflects a serene sky with pastel hues, inviting relaxation and leisure.

Windsor, CA, 1-Bedroom SN #1

An inviting outdoor pool is centered within a spacious courtyard, surrounded by lounge chairs and shaded umbrellas. Lush greenery lines the perimeter, and the sky features soft hues of pink and blue as the sun begins to set.

Windsor, CA, 3-Bedroom Dlx #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 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.