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, 119 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, 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.

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, 207 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.

Guest house in Healdsburg

An inviting Mediterranean-style patio is filled with vibrant mosaics and potted plants. Two charming chairs surround a small table under a pergola, providing a shaded area, while lush greenery enhances the area’s privacy and tranquility.

4.95 out of 5 average rating, 186 reviews

Mediterranean Getaway with breakfast Healdsburg

An attractive, ultra-romantic, almost-a-cottage Bed&Breakfast is waiting for you in our restored 1930s-era home in a peaceful corner of northern Sonoma County. Ours is a quiet rural road nestled in beautiful oaks, redwoods, California bay, and buckeye trees near the bottom of Fitch Mountain, some 100’ above the Russian Rive. Fitch Mountain is known for its interesting local history, eclectic building styles, beautiful views, secluded neighborhoods, and friendly spirit.

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, 438 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, 234 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!

4.97 out of 5 average rating, 606 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.

A two-story home is presented with a light-colored exterior, complemented by large windows. A spacious driveway leads to the attached garage, while a covered porch area with seating is visible. The surrounding yard features low-maintenance landscaping and a wooden fence providing privacy.

4.94 out of 5 average rating, 223 reviews

Centrally Located, Modern Wine Country Estate

Conveniently located in the heart of wine country! Just minutes away from famous wineries, breweries, world class-dining, family 'Epicenter', Sonoma County Airport and downtown Santa Rosa. This home features a gorgeous, new modern kitchen, outdoor dining area under the pergola with a BBQ and fire pit, pool table, washer and dryer, free wifi and parking. Welcome home! - Sincerely, Your Wine Country Concierge.

Popular amenities for outdoor seating rentals in Windsor

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

A spacious living area is designed for relaxation, featuring a comfortable light-colored sofa with decorative throw pillows. A large window allows natural light to fill the space, highlighting the modern décor. A stylish coffee table rests in front of the seating, complemented by a vibrant area rug.

4.93 out of 5 average rating, 213 reviews

Wine Country Getaway | Hot Tub + Near Park

4.91 out of 5 average rating, 140 reviews

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.

Home in Healdsburg

Healdsburg 2br Cottage with Private Yard!

4.9 out of 5 average rating, 189 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.

4.96 out of 5 average rating, 101 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

4.95 out of 5 average rating, 170 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

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, 677 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, 102 reviews

Wine Country Villa Heated Pool Hot Tub Upper Level

Apartment rentals with outdoor seating

4.97 out of 5 average rating, 875 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, 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.

Flat 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.

Flat in Sebastopol

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

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.

Flat 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.

Flat in Santa Rosa

Sonoma County Getaway: Mins to Wineries & Downtown

4.97 out of 5 average rating, 198 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, 523 reviews

Flat 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.

Flat in Petaluma

Victorian Garden Apartment - walk to downtown

Apartment 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.

Apartment 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.