Pet-friendly vacation rentals in Healdsburg

4.91 out of 5 average rating, 464 reviews

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

Welcome to our private, renovated, personal spa in the woods. Including a large wood-burning Finnish sauna, it features a picturesque deck with hot/cold plunge over breathtaking untouched forest with fire pit vineyard-side. This all-cedar cottage is nested below Halleck Vineyard, one of Sonoma County’s prestigious wineries. A perfect retreat, you are centrally located for the best Sonoma has to offer Sonoma County Wine Tastings (0-20 mins) Bodega Bay (20 mins) Armstrong Giant Redwoods (30 mins)

WalkabilityPetsEV charging

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

4.91 out of 5 average rating, 259 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!❤

PetsWalkabilityQuiet

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.

5 out of 5 average rating, 119 reviews

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!

PetsWalkabilityFamily

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, 106 reviews

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

Outdoor spacesPetsAir conditioning

4.94 out of 5 average rating, 234 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.

Outdoor spacesPetsQuiet

5 out of 5 average rating, 714 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

Outdoor spacesWalkabilityFamily

4.93 out of 5 average rating, 177 reviews

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.

Outdoor spacesWalkabilityBeach

An open living space seamlessly connects with an outdoor deck, featuring a dining table set for several. Natural light floods the area, highlighting wooden flooring and a cozy rug. Lush greenery can be seen in the garden area beyond the deck, creating a serene atmosphere.

4.95 out of 5 average rating, 205 reviews

Wine Country Cottage Walkable to River or Downtown

Centrally located retreat 5 blocks from downtown, Russian River and 3 blocks from at least 9 wineries. Living room fully opens to private deck w/BBQ, outdoor kitchen, dining space and fire place. Gourmet equipped kitchen with many cooking amenities to enjoy wine and a great meal in the garden patio or BBQ outside and relax. Luxury bathroom with heated towel rack, heated floor and bidet. A small cozy two bedroom with many amenities and thoughtful touches.

WalkabilityPetsHeating

4.98 out of 5 average rating, 128 reviews

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

Experience the ultimate Wine Country escape. The property sits on 11 private acres, offering complete privacy, peaceful surroundings, and stunning 360-degree views, including the iconic Mount Helena. Ideally located near Calistoga (15 minutes) and Healdsburg (20 minutes) and surrounded by top-rated wineries. Whether you’re here for wine tasting, relaxation, or a scenic getaway, this property delivers space, comfort, and unforgettable views.

Outdoor spacesPetsHot tub

4.99 out of 5 average rating, 177 reviews

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!

Outdoor spacesWalkabilityGrill

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.

4.88 out of 5 average rating, 361 reviews

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.

PetsWalkabilityHot tub

4.93 out of 5 average rating, 653 reviews

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

WalkabilityOutdoor spacesCleanliness

Popular amenities for Healdsburg pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly home rentals with a pool

A serene infinity pool extends towards the horizon, bordered by lush greenery. Eight lounge chairs, with two umbrellas, face the pool, inviting relaxation. A wooden structure sits in the background, along with a staircase leading to the home, all under a soft, pastel sky.

4.92 out of 5 average rating, 145 reviews

Farpoint: Heated Infinity Pool, Mountain Views

Outdoor spacesPetsPool

4.91 out of 5 average rating, 191 reviews

The villa is set against a colorful sunset, highlighting its two-story structure. A large pool reflects the warm hues of the sky, while well-maintained landscaping surrounds the outdoor area. Soft lighting from the home creates an inviting ambiance.

Villa in Santa Rosa

Villa Annadel - Stunning 5 Bedroom with a Pool

WalkabilityPetsHospitality

4.97 out of 5 average rating, 158 reviews

Villa in Santa Rosa

Private 1+ acre, Bocce, Waterfall, Free Pool Heat

Outdoor spacesPetsComfort

The backyard showcases a newly built pool surrounded by a spacious wood deck, featuring in-pool loungers. A picturesque sunset casts warm light on the landscape, while the home and outdoor seating areas are framed by tall trees, creating a serene country atmosphere.

4.98 out of 5 average rating, 122 reviews

Sonoma Retreat w/Pool/Spa/Barn/OD Kitchen/Orchard

Outdoor spacesWalkabilitySleep quality

4.99 out of 5 average rating, 211 reviews

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

PetsWalkabilityBathroom

4.96 out of 5 average rating, 124 reviews

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

Outdoor spacesWalkabilitySleep quality

4.98 out of 5 average rating, 132 reviews

Wine Country Retreat- Privacy-Spa/Pool/Games

WalkabilityPetsAir conditioning

A lively pool area is featured, showcasing a clear blue swimming pool surrounded by lounge chairs and vibrant inflatable floats. A shaded cabana provides a relaxing spot, while a nearby umbrella offers additional shade. The surrounding landscape includes lush greenery and a stone wall.

4.98 out of 5 average rating, 196 reviews

Sebastopol Gem, The Birdhouse. Hottub. Pool. Views

WalkabilityPetsBackyard

Pet-friendly home rentals with a hot tub

4.89 out of 5 average rating, 454 reviews

The exterior view of the cabin showcases a grey wooden façade, complemented by a vibrant red door. Two orange chairs are positioned on a wooden deck, surrounded by lush greenery and a decorative maple tree. Large windows allow natural light to illuminate the interior space.

Cabin in Guerneville

Velouria - Hot Tub, Woodstove, Redwoods.

Outdoor spacesWalkabilityHeating

5 out of 5 average rating, 121 reviews

Pixel Place - A Private Arcade + Outdoor Sanctuary

PetsWalkabilityComfort

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.

4.9 out of 5 average rating, 106 reviews

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

WalkabilityPetsLayout

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.

4.94 out of 5 average rating, 319 reviews

Sonoma County Historical Ranch House on a Vineyard

Outdoor spacesPetsCheck-in

4.96 out of 5 average rating, 218 reviews

Home in Forestville

Hilltop Haven Retreat | Scenic Hydro-Spa + Sauna

PetsWalkabilityAccess

4.97 out of 5 average rating, 155 reviews

Home in Sonoma

Stunning Sonoma | HOT TUB | Game Room | Sleeps 6

WalkabilityOutdoor spacesHospitality

4.9 out of 5 average rating, 305 reviews

A hot tub is positioned on a wooden deck, surrounded by trees. Nearby, a dining area features a table and chairs under a large umbrella. The warm ambiance is enhanced by the glow of lights visible through large windows in the background.

Home in Forestville

PEACE & QUIET Close 2 Wine Hot Tub Fenced Yard

Outdoor spacesPetsBeach

4.94 out of 5 average rating, 159 reviews

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

Outdoor spacesPetsBiking

Pet-friendly house rentals

Superhost

A spacious hot tub, surrounded by lush greenery, is set on a manicured lawn. Beyond, expansive views of the vineyards and rolling hills are visible under a clear blue sky, creating a tranquil outdoor retreat.

4.81 out of 5 average rating, 181 reviews

Spectacular Vineyard View!! SPA, Close to Plaza!

PetsWalkabilityFamily

4.95 out of 5 average rating, 169 reviews

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

Outdoor spacesPetsLaundry

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.

4.89 out of 5 average rating, 425 reviews

Wine Country Cottage in Healdsburg

PetsOutdoor spacesDecor

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, 119 reviews

Centrally Located Modern Wine Country Home

PetsWalkabilityLong stay

4.97 out of 5 average rating, 121 reviews

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

Outdoor spacesPetsLaundry

4.97 out of 5 average rating, 137 reviews

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!

Outdoor spacesWalkabilityAmenities

A dining area features a simple wooden table surrounded by four matching chairs. Natural light filters through the window, enhancing the light-colored walls and warm wooden floor. A ceiling fan is positioned above, providing a cool breeze in the space.

4.94 out of 5 average rating, 179 reviews

West End Neighborhood Cottage

WalkabilityOutdoor spacesParking

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.