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Pet-friendly vacation rentals in Healdsburg

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Quick stats about vacation rentals that are pet-friendly in Healdsburg

  • Total vacation rentals

    Explore 50 vacation rentals in Healdsburg

  • Nightly prices starting at

    Healdsburg vacation rentals start at €86 per night before taxes and fees

  • Verified guest reviews

    Over 4,250 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Healdsburg vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Healdsburg rentals

  • 4.9 Average rating

    Healdsburg stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated pet-friendly home rentals in Healdsburg

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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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

❤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!❤

4.9 out of 5 average rating, 265 reviews
Top guest favorite
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!

5.0 out of 5 average rating, 123 reviews
Superhost
An aerial view reveals a spacious property surrounded by lush vineyards. The main house is situated to the left, with a sparkling pool adjacent to it. A winding road leads through the greenery, while gentle hills stretch into the distance under a clear blue sky.
Home in Healdsburg

Dry Creek Ranch ~ (Tariff Discount) Hot Tub & Pool

Enjoy an idyllic wine tasting weekend for 3-4 couples, have fun with the whole family (pets welcome) or find adventure along the world famous Dry Creek Road. This property boasts a main house, pool house & Game barn. The main house sleeps 10. The pool house features a 70” flatscreen, a Live Edge tasting bar and Lanai. The property is only 1.4 miles from Healdsburg’s square. Take a gentle bike ride into town or stay put – pour wine, soak in the hot tub, and watch the sun set over the vineyards

4.9 out of 5 average rating, 107 reviews
Top guest favorite
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.
Home in Santa Rosa

Wine Country Villa Heated Pool Hot Tub Upper Level

Welcome to Brush Creek, 20-minutes from Sonoma, Napa, Russian River, Alexander, and Knight's Valleys. Our cozy villa offers 2 unique bedrooms, including a regal King Master suite and a second King bedroom. Complimentary EV charging. Healdsburg, Calistoga, and the trendy Barlow are easily accessible. Brush Creek: where comfort, luxury, and character converge for an unforgettable wine country retreat. Heated Pool (fees may apply). No one else in the property during your stay. SVR26-101

4.97 out of 5 average rating, 110 reviews
Top guest favorite
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.
Home in Santa Rosa

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!

4.97 out of 5 average rating, 241 reviews
Guest favorite
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.
Home in Santa Rosa

Centrally Located Modern Wine Country Home

Your wine country retreat awaits you. This gorgeous home features a new modern kitchen, outdoor seating area, washer and dryer, free WiFi and parking. This home is conveniently located in the heart of wine country minutes away from Sonoma wineries, breweries, Sonoma County Airport, downtown Santa Rosa, downtown Sebastopol and great dinning. Due to COVID we clean and sanitize the house thoroughly before and after each stay. Welcome to your home away from home!! Your concierge Ana

4.93 out of 5 average rating, 122 reviews
Top guest favorite
Home in Healdsburg

Modern Healdsburg Retreat • Hot Tub, Bocce & Views

Vineyard views + hot tub under the stars—modern Healdsburg, 5 min to the Plaza. Set in Dry Creek Valley, this design-forward retreat feels a world away—yet you’re minutes from top wineries, tasting rooms, and dining. Slow mornings with coffee overlooking the vines. Golden-hour dinners outside. Evenings in the hot tub with sunset views and total privacy. Designed for relaxed Wine Country living with bocce, outdoor lounge spaces, and seamless indoor-outdoor flow.

4.93 out of 5 average rating, 179 reviews
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

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!

4.85 out of 5 average rating, 157 reviews
Top guest favorite
Cottage in Geyserville

Country Carriage House in Downtown Geyserville

Linger over coffee on your quaint patio amongst 6 acres downtown in sweet Geyserville. An industrial loft vibe with wine country bones—the cottage is modern/rustic meets country-correct. Immerse yourself in country life or walk to downtown Geyserville for an Aperol Spritz. Truly where design meets refuge. Goats, horses, dogs, one heifer 🐄 named Francis, and one farm cat named Leo on property. Fully fenced front yard and back patio!

4.99 out of 5 average rating, 181 reviews
Guest favorite
A pathway leads to a welcoming front porch, flanked by greenery and blooming flowers. The light-colored home is partially shaded by surrounding trees, creating a serene approach. The yard features fresh landscaping with mulch and various plants, enhancing the inviting entrance.
Home in Healdsburg

Peaceful location, hot tub, fire pit, game room!

Feel your stress melt away as you wind your way down a country road to our little piece of heaven in wine country. Our cozy home is a great starting place for your Healdsburg adventures! Private yard, super comfortable beds, well equipped kitchen, cozy living room with fireplace, free wifi and cable, game room with pool table, poker, Skee-ball plus a wonderful outdoor dining area. Just a 5 minute drive to downtown Healdsburg.

4.88 out of 5 average rating, 363 reviews
Top guest favorite
Home in Healdsburg

Healdsburg Garden House

Hidden gem Best Value Ideal space for reunions and bridal parties (no events) Clean, Cozy & Private House Near Healdsburg Town Square. 20% discount for self serve rental Healdsburg Kayak Company Discount code - HEALDSBURGGARDEN20 Centrally located for Sonoma county day trips… Covered redwood deck with gas grill 50” HDTVs and fast 1 GB Wi-Fi. Fully stocked kitchen w/ dishwasher. New A/C and heating. TOT #798N

4.93 out of 5 average rating, 655 reviews
Top guest favorite
A bright bedroom is furnished with a metal bed frame topped with white linens. Soft gray curtains frame the window, allowing natural light to fill the space. A dark dresser stands against the wall, and a small area rug adds texture to the floor.
Apartment in Cloverdale

2 Bedroom Flat With Short Walk to Downtown

Keep it simple at this peaceful and centrally-located place. Our 100+ year old vacation home has a classic vintage vibe with newly renovated modern touches. The upstairs apartment features 2 bedrooms and 1 bathroom. It is only half a block from downtown Cloverdale where you’ll find restaurants, bars, shopping and live music in the summer. This is the perfect place to enjoy a family vacation or a friends getaway!

4.94 out of 5 average rating, 143 reviews

Popular amenities for Healdsburg pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly home rentals with a pool

Top guest favorite
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

5.0 out of 5 average rating, 720 reviews
Top guest favorite
Home in Santa Rosa

Wine Country Retreat | Pool, Hot Tub + Vibes

4.97 out of 5 average rating, 234 reviews
Guest favorite
The serene pool area is surrounded by lush greenery, featuring modern lounge chairs and large umbrellas for shade. The sparkling water invites relaxation, while a covered outdoor space extends from the home, providing a seamless transition to the tranquil outdoor retreat.
Home in Sebastopol

Serene Wine Country Retreat with Pool & Hot Tub

4.89 out of 5 average rating, 117 reviews
Top guest favorite
A private outdoor pool area features a sleek, blue pool surrounded by smooth stone tiles. Chaise lounges are positioned nearby, inviting relaxation. The setting is complemented by a rustic wooden structure and a charming home with a brick chimney, set against a colorful sunset sky.
Home in Sonoma

Vineyard-House Escape in Sonoma Wine Country

4.99 out of 5 average rating, 214 reviews
Guest favorite
A modern kitchen features a spacious island with three woven bar stools. Hexagon-tiled walls in a soothing grey tone complement open shelving displaying dishware. Large windows allow natural light to fill the space, with greenery visible outside.
Home in Sonoma

Modern wine country stunner with pool & pickleball

4.95 out of 5 average rating, 128 reviews
Top guest favorite
Home in Guerneville

Modern farmhouse (pool can be heated year round)

4.99 out of 5 average rating, 191 reviews
Top guest favorite
Home in Santa Rosa

Spacious 5 BR 3BA Pool EV Charger Group Getaway

4.98 out of 5 average rating, 124 reviews
Top guest favorite
A private outdoor area features a hot tub adjacent to a wooden deck. A white dining table is positioned for meals, surrounded by lush greenery. Soft lighting hangs above, adding to the relaxed setting. A window on the house offers natural light to the space.
Home in Santa Rosa

Pacific Gardens Retreat

4.98 out of 5 average rating, 213 reviews

Pet-friendly home rentals with a hot tub

Guest favorite
Aerial view of a modern farmhouse villa surrounded by lush, rolling hills. Vibrant flowering trees line the property, alongside a grassy landscape that slopes gently upward. The natural setting offers a sense of seclusion, with trees creating a backdrop against clear blue skies.
Villa in Santa Rosa

Farmhouse Villa w/ Captivating Views & Hot Tub

4.98 out of 5 average rating, 130 reviews
Superhost
Home in Healdsburg

Redwood Riverfront - Hot Tub and Tastings Included

4.83 out of 5 average rating, 150 reviews
Guest favorite
A bright kitchen features sleek white cabinetry and a spacious island with a light marble countertop. Pendant lights hang above the island, while large windows allow natural light to fill the space. Stainless steel appliances add a modern touch to the overall design.
Home in Windsor

Gourmet Kitchen in Wine Country w/Hot Tub + Office

4.95 out of 5 average rating, 116 reviews
Top guest favorite
Home in Santa Rosa

Botany House Designer Home with Hot Tub

4.96 out of 5 average rating, 131 reviews
Guest favorite
A spacious great room features a high wood-beamed ceiling and natural light pouring in through skylights. Comfortable lounge seating is arranged near a fireplace, with a large dining table designed to accommodate multiple guests, creating an inviting space for gatherings.
Cabin in Forestville

The Black Sheep - Wine Country • Hot Tub • Theater

4.94 out of 5 average rating, 163 reviews
Guest favorite
An outdoor fire pit surrounded by four wooden chairs offers a welcoming gathering space. The stone patio extends outward, framed by lush greenery and the vibrant hues of sunset. A vineyard is visible in the background, enhancing the natural setting.
Cottage in Sebastopol

Stunning Sauna Cottage Retreat on Private Vineyard

4.91 out of 5 average rating, 471 reviews
Top guest favorite
A covered hot tub is surrounded by curtain drapes and string lights, providing a cozy ambiance. The tub is filled with water that displays a soothing green hue, inviting relaxation in a tranquil outdoor setting.
Home in Geyserville

Updated 5 BR house w/ hot tub - walk to downtown!

4.99 out of 5 average rating, 142 reviews
Top guest favorite
Home in Forestville

Hilltop Haven Retreat | Scenic Hydro-Spa + Sauna

4.96 out of 5 average rating, 225 reviews

Pet-friendly house rentals

Top guest favorite
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

4.89 out of 5 average rating, 426 reviews
Top guest favorite
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.
Home in Santa Rosa

Casa de Gamay - Your Home Away From Home

5.0 out of 5 average rating, 199 reviews
Top guest favorite
An outdoor seating area features two cushioned chairs and a wooden coffee table set atop a textured area rug. A vase with lemon branches and a wine bottle accompany glasses, inviting guests to enjoy leisurely moments in a peaceful garden setting.
Home in Santa Rosa

Luxury wine country home 5 bedroom

4.98 out of 5 average rating, 109 reviews
Guest favorite
A modern living area is shown, featuring a mid-century style blue sectional sofa adorned with decorative pillows. A light wood coffee table sits on a geometric patterned rug. Wall art depicting a serene landscape is displayed, along with circular mirrors that enhance the room's character.
Home in Cloverdale

Cozy Hisorical Home Walking Distance to Downtown!

4.97 out of 5 average rating, 138 reviews
Top guest favorite
Home in Santa Rosa

Pup Friendly GET Away to WINE Country- 3 bdrm Home

4.96 out of 5 average rating, 296 reviews
Top guest favorite
A modern living area features a large dark green sofa complemented by a cozy white chair and a stylish coffee table. Natural light streams through multiple windows, illuminating a patterned area rug. A dining area and kitchen are visible in the background.
Home in Calistoga

Calistoga Tejas Trails

4.97 out of 5 average rating, 124 reviews
Top guest favorite
Home in Guerneville

Riverfront Home with Private Dock on Russian River

4.9 out of 5 average rating, 220 reviews
Top guest favorite
A cozy living area features a light-colored sofa, complemented by a vibrant floral arrangement on a nearby table. Large windows offer broad views of the river and lush hills beyond, inviting natural light into the space.
Home in Jenner

Casa Panama: Relax in Luxury on the Sonoma Coast

4.95 out of 5 average rating, 173 reviews

When is the best time to visit Healdsburg?

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Avg. price€287€304€333€329€420€349€340€303€306€302€287€317
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