Property Category: Healdsburg

Welcome to The Dragonfly, an exquisite oasis of luxury nestled in the heart of wine country. This sophisticated vacation rental offers an unforgettable experience, combining tranquility, elegance, and modern comfort. With its stunning outdoor area this property promises the ultimate retreat for adults seeking an escape from the hustle and bustle of everyday life. As you enter the estate you'll be enchanted by the tastefully designed interior, adorned with high-end furnishings and…

Experience the beauty of Sonoma County with a stay at this charming farm house. Boasting 3 bedrooms and 3.5 bathrooms, this historic property offers a glimpse into the rich heritage of wine country. As you step inside, you'll be greeted by a spacious gourmet kitchen that seamlessly flows into the dining area, living room, and wrap-around deck. This open layout ensures that everyone can gather together and enjoy the exceptional views that…

Welcome to Healdsburg Homestead! In the heart of Sonoma County’s Dry Creek Valley, this peaceful farmhouse sits along a quiet country road, surrounded by vineyards, gardens, and the gentle sound of a seasonal creek. Though it feels worlds away, you’re just 5 minutes from downtown Healdsburg’s tasting rooms, boutiques, and acclaimed restaurants. Wake up to birdsong and garden views, spend the day wine tasting or paddling on Lake Sonoma, then unwind in…

Our 1880s cottage has been part of Healdsburg’s story for over a century—now it’s ready to be part of yours. Just two blocks from the Plaza, this dog-friendly vacation rental blends vintage charm with modern comforts. Walk to world-class tasting rooms, restaurants, and boutiques, then return to your cozy retreat in the heart of Sonoma County wine country. What You’ll Love • Living room with comfy seating for relaxing after wine tasting…

Retreat to the exquisite Heron House, a riverside haven where the grandeur of the Redwoods meets the flowing beauty of the Russian River. This special riverfront dwelling offers direct access to a private beach and is located just minutes from downtown Healdsburg. Tucked away on North Fitch Mountain's wooded knoll, the home provides a secluded feel above the river. The Heron House is a 3-bedroom, 2-bathroom home designed to accommodate up to…

Freshly remodeled and ready to welcome you, this stunning property offers the perfect Wine Country escape. Just minutes from Dry Creek and Alexander Valley wineries and a 10-minute drive to Healdsburg Plaza, the home combines modern comfort with serene surroundings. The main house features an open-concept layout leading to an expansive entertainment deck overlooking the property. The fully equipped kitchen with island seating flows seamlessly into the living and dining areas, offering…

Escape to Private Vineyard Haven, a luxurious 2BR/2BA Sonoma home where modern comfort meets vineyard charm. Spanning 1,439 square feet, the home features a gourmet chef’s kitchen and floor-to-ceiling folding glass doors that open completely, blending indoor living with stunning views of your private Sauvignon Blanc vineyard and California sunshine. This home offers a perfect blend of comfort and care. Guests enjoy all the amenities while experiencing hospitality that makes them feel…

Nestled between redwoods and vineyards, Puccioni Paradise is a peaceful Sonoma escape for two guests (plus a third for an additional fee), offering a perfect blend of comfort, nature, and Wine Country charm. Just a 15-minute drive to Healdsburg Plaza, you’re close to restaurants, shops, and tasting rooms while enjoying ultimate privacy and tranquility. This home offers more than beautiful interiors and breathtaking surroundings—our hospitality elevates the experience. Guests enjoy seamless check-in,…

Escape to Redwood River House, a beautifully updated 2BR/1BA cottage along the Russian River, just 1.5 miles from downtown Healdsburg. Perfect for couples, small families, or friends, this upscale getaway blends comfort, nature, and Wine Country charm. Beyond the cozy living spaces and scenic views, our home provides a level of hospitality guests appreciate. We’re attentive, responsive, and dedicated to making your stay smooth, comfortable, and enjoyable. Local Winery Partnerships | Elevate…

Tucked along the Russian River, just 1.5 miles from Healdsburg Plaza, River View Lodge is a private, peaceful retreat perfect for romantic getaways, family vacations, or remote work with a view. With stunning river frontage, a private dock, two kayaks, a hot tub, and an expansive deck over the water, this home offers an unforgettable Wine Country experience. While this home impresses with its comfort and setting, it’s the personal touches that…

Relax and recharge at Riverbend Retreat, a warm and inviting 3-bedroom, 1.5-bath bungalow nestled in a peaceful neighborhood just 5 minutes from Healdsburg Plaza. Perfect for couples, families, or a group of friends, this home blends rustic charm with modern comfort, offering an ideal base for exploring Sonoma wine country or simply unwinding by the river. Guests love the comfort and charm of our home, but it’s the thoughtful hospitality that keeps…

Slow down, unplug, and breathe in the beauty of riverfront living at Rivers Breeze, a charming 2-bedroom, 1-bath main house with a private 1-bedroom, 1-bath lower-level suite, nestled along a peaceful stretch of the Russian River, just minutes from downtown Healdsburg and nearby wedding venues. Perfect for couples, families, or friends, this retreat invites you to reconnect with nature, loved ones, and yourself. We pair the comfort and charm of the home…

Escape to Sanctuary on Lytton, an extraordinary 11.67-acre estate in the heart of Alexander Valley, just 7 minutes from Healdsburg Plaza. This exclusive retreat offers ultimate privacy, breathtaking mountain and valley views, and a serene bird refuge, making it ideal for family reunions, friends’ getaways, corporate retreats, or creative workshops. Enjoy all the comforts of a beautifully appointed home, enhanced by our attentive hospitality. We provide guidance, thoughtful touches, and support to…

Escape to Santini, an exclusive farmhouse estate in the heart of Dry Creek Valley, just 8 miles from Healdsburg Plaza. Surrounded by world-class vineyards, this newly built home combines seclusion, comfort, and modern luxury, making it perfect for families, couples, or groups of friends seeking a Wine Country retreat. This home offers a perfect blend of comfort and care. Guests enjoy all the amenities while experiencing hospitality that makes them feel warmly…

Serenity on Dragonfly is a charming 3-bedroom country home nestled in the heart of Wine Country, just minutes from the vibrant Healdsburg Plaza with its top-rated restaurants and renowned tasting rooms. Merriam and Limerick Lane wineries are within walking distance, offering a truly immersive wine country experience. Beyond the stunning home and location, our guests love the personal touch we provide. We’re attentive, responsive, and committed to making sure your Wine Country…

Where urban sophistication meets wine country charm, Vineyard Vue is a beautifully remodeled farmhouse just blocks from downtown Healdsburg and a short 10-minute walk to the historic Healdsburg Plaza. Blending character, comfort, and breathtaking vineyard views, this home is perfect for romantic getaways, family vacations, or friends’ retreats. Highlights & Features • 2 king bedrooms with en-suite bathrooms + fold-out sofa in office (additional sleeping for 2) • Spacious open-concept living area…

Discover Xanadu Healdsburg, a stunning Blu Home retreat in the heart of Sonoma County Wine Country. Perfectly located just 5 minutes from Healdsburg Plaza, you’re steps from world-class wineries, award-winning restaurants, and boutique shopping across the Dry Creek, Alexander Valley, and Russian River regions. This eco-conscious luxury home combines modern design with green solar technology, offering one-level living with seamless indoor-outdoor flow through glass-walled Nano doors. The great room, gourmet kitchen, and…

Step into Fitch Street Escape, a chic and recently remodeled historic home just 2 blocks from Healdsburg Plaza. Perfectly located in the heart of Sonoma Wine Country, this sophisticated retreat offers easy access to award-winning restaurants, boutique shopping, and world-class wine tasting. Blending modern design with historic charm, this bright, open-concept home features 2 bedrooms, 2 full bathrooms, and high-end finishes throughout. A chef’s kitchen with stainless steel appliances, sleek surfaces, and…

Discover Heavenly Hideaway, a beautifully remodeled historic home just 2 blocks from Downtown Healdsburg Plaza. This sophisticated retreat offers immediate access to Healdsburg’s award-winning restaurants, boutique shopping, and premier wine tasting, all while providing a serene sanctuary to relax and recharge. Blending modern luxury with Wine Country charm, the home features an open-concept chef’s kitchen with stainless steel appliances, sleek surfaces, ample storage, and an inviting island, perfect for cooking, entertaining, or…

Experience the best of Healdsburg living at Heart of Healdsburg, a charming 2-bedroom Tuscan-style cottage just steps from the vibrant Healdsburg Plaza. This bright and airy retreat combines wine country charm with modern comforts, offering an ideal base for couples, families, or friends seeking an unforgettable Sonoma getaway. Wake up to morning sunlight streaming through your windows, enjoy coffee on your private patio, and soak in the peaceful surroundings before heading out…

This Elegant Villa offers World Class Views, High End Appointments, a Chef Inspired Kitchen, Indoor and Outdoor Dining and Entertainment Areas, including a Firepit to enjoy the evening with family and friends. The property is private yet only 10 minutes to town, with spectacular views of the entire valley and beyond. The Estate offers 4 Bedrooms and 3.5 baths, including Master Suite with jacuzzi tub and open floor plan that complements indoor…