Vacation rentals with outdoor seating in Healdsburg

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Healdsburg

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

A spacious studio guest house is shown, featuring a comfortable queen bed adorned with soft linens. A cozy seating area is present with a plush couch, and a wall-mounted TV is visible. Natural light fills the room through large windows, complemented by wooden beams on the ceiling.

Guesthouse in Healdsburg

4.98 out of 5 average rating, 292 reviews

Alexander Valley: Wine Lover and Cycling Paradise

The Finca Guest House is a beautiful modern & private unit, which offers country seclusion just a short hop into Healdsburg. Three private outdoor spaces for your use! Coffee patio, wine patio, goat patio--your choice! World-class biking out the door. Guest House will be thoroughly cleaned per Airbnb guidelines! *This property has farm animals so no outside animals allowed. See Rules and Policies notes Gas grill w/burner is available for outdoor cooking. NO full kitchen. Sonoma Co. TOT#3191N

Superhost

The exterior of the barn cottage is featured, showcasing a two-story structure with large windows illuminated in a warm glow. The entrance is adorned with wooden doors and a star accent. A spacious deck is visible above, providing an inviting outdoor space.

Cottage in Healdsburg

4.94 out of 5 average rating, 187 reviews

❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤

❤New! Welcome to the "The Elegant Barn", our newly built stylish Barn Cottage in the HEART of wine country! Our *INSTAWORTHY* barn cottage boasts a HOT TUB, panoramic vineyard VIEWS, comfy furnishings & convertible glass indoor/outdoor doors to bring the outdoors inside! LOCATION, LOCATION, LOCATION! Set on a historic vineyard property on Dry Creek Road, the location of Healdsburg's most famous wineries, and an easy walk, bike ride or drive to many of the best wineries in the area! PETS OK!❤

Top guest favorite

A covered outdoor seating area features a rustic wooden ceiling with pendant lighting. Seating for four is arranged around a central table, complemented by a built-in outdoor kitchen with a grill and pizza oven. Lush greenery decorates the background.

Home in Healdsburg

4.99 out of 5 average rating, 102 reviews

Luxe Healdsburg Home ~ Sauna, Hot Tub, EV Charger

Welcome to your own private slice of wine country paradise—a stunning vineyard estate amidst rolling hills. This luxurious home is beautifully designed and combines contemporary architecture with a warm, inviting ambiance. Whether you’re sipping wine on the patio, enjoying the serene views, or gathering with loved ones, this home provides the perfect setting to create unforgettable memories with family and friends. Escape, relax, and indulge in the best of Healdsburg’s charm and tranquility.

Top guest favorite

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.

Guest suite in Healdsburg

4.93 out of 5 average rating, 446 reviews

Pony Ranch Vineyard Estate with Pool

Guest House with private entrance on gorgeous gated Vineyard Estate. Overlooks pool and vineyards with views to Mount St. Helena. Gas fireplace, refrigerator, microwave, Keurig coffee maker, queen bed. Seasonal private pool with fabulous views, occasionally shared with owners. Toilet and sink separate from shower. 8 minutes to the Healdsburg Plaza. Less than a mile from 3 wineries, very close to dozens more. Agricultural Education Programs available. Sonoma County TOT Certificate 1362N

Top guest favorite

A bright yellow exterior is complemented by vibrant flowers in front of the window. Lush greenery surrounds the area, highlighting a tranquil outdoor space. The view includes trees and open fields, suggesting a peaceful and natural setting.

Home in Healdsburg

4.93 out of 5 average rating, 599 reviews

Healdsburg Garden House

Enjoy a real Sonoma County Experience Best Value in the Valley Organic grapes, hops, flower and vegetable gardens Centrally located home away from home Large Covered Redwood Deck with Gas Grill NEW A/C and Heating (controls in each bedroom) Super clean and sanitized Private, spacious & comfortable Fully Stocked Kitchen w/ Dishwasher 50” HDTV’s in each room (HBO, Showtime, Netflix, YouTube…) 1 GB High Speed Ethernet Level Walk to Town Square and Russian River Beach TOT # 798N

Guest favorite

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

4.9 out of 5 average rating, 122 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 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

Top guest favorite

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.

Guesthouse in Healdsburg

4.96 out of 5 average rating, 124 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.

Superhost

The exterior of the villa is framed by tall, slender cypress trees, creating a serene entrance. The structure features a flat roof and large windows, with a backdrop of rolling vineyards and soft, distant hills illuminated by the warm light of sunset.

Villa in Healdsburg

4.94 out of 5 average rating, 171 reviews

Hilltop Vista Villa

Set on an Acre by Fitch Mountain Park and Open Space Preserve, Hilltop Vista Villa offers a quiet private setting, spectacular views of world class vineyards, private access to hiking trails and proximity to the Russian River beach. This inviting single level retreat has an open floor plan with lots of sunshine. The open kitchen features stainless steel appliances, custom cabinetry, and a granite topped island. The Master Suite includes a custom soaking tub.

Top guest favorite

A charming single-story cottage is framed by vibrant plants, showcasing a well-kept lawn. Large windows invite natural light, while a welcoming front door is visible. The surrounding garden features colorful flowers, enhancing the tranquil setting.

Home in Healdsburg

5 out of 5 average rating, 173 reviews

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!

Top guest favorite

Two modern, white structures stand beneath a large green tree against a clear blue sky. The buildings feature large glass windows, allowing for natural light. The area is surrounded by open grass, contributing to a relaxed and spacious atmosphere.

Home in Healdsburg

4.85 out of 5 average rating, 124 reviews

Three-Building Healdsburg Homestead with Wine Barn

Your Healdsburg Homestead for launching wine country adventure! Recently remodeled, 3 buildings on 1/2 acre, including a barn with a winetasting bar & game room! Great for families and groups. Perfectly located for cycling on the legendary Eastside/Westside loop. For wine lovers, we are across the street from Rodney Strong Vineyard and the amazing sparkling wines of the beautiful J Vineyard. Best of all, Healdsburg Plaza is just a short hop away!

Top guest favorite

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

4.97 out of 5 average rating, 597 reviews

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. 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

Guest favorite

A bright living area features a spacious white sectional couch and a wooden coffee table. An expansive bookshelf holds various items, with a television and fireplace being focal points. Large glass doors open to a garden, bringing in natural light and outdoor views.

Guesthouse in Healdsburg

4.97 out of 5 average rating, 207 reviews

Healdsburg Contemporary Cottage With Lush Backyard Patio

Your private Healdsburg retreat—just a 4-minute walk to downtown wine tasting rooms, restaurants, shops, and the Farmers Market. This stylish guest cottage offers parking in front of a private entry, garden with al fresco dining, BBQ, lounge area, and a fully equipped Pilates studio. Designed with international contemporary art and thoughtful touches, it’s perfect for a weekend escape or a longer stay while house hunting.