Luxury rentals in Healdsburg

Magical Wine Country Compound – Epic Views & Pool

Escape to a Magical Wine Country Retreat Perched atop a hill with sweeping views of 47 private acres, this newly renovated and impeccably styled compound offers the ultimate blend of seclusion and sophistication. Soak in sunsets from the heated pool or unwind in the hot tub under the stars. Justminutes from the charming towns of Geyserville and Healdsburg, enjoy a balance of quiet countryside and vibrant wine country food, drinks and culture. Relax, connect, and create unforgettable memories!

Sonoma-Napa Private Retreat by the Hills + Hot Tub

Rated in the top 5% Guest Favorites, this modern country home offers luxury and classic California indoor-outdoor living. Set on an expansive lot with lawns, fruit trees and a garden, it is surrounded by peaceful hills on three sides. Explore over 250 Sonoma and Napa wineries, hot springs, beaches, rivers, and redwood forests all within 30 miles. While completely private, Santa Rosa city amenities are just 10 minutes away. Ideal for wine country getaway, wedding trip, remote work or staycation.

Luxury Modern Home w/ Infinity Pool - 3400 sq ft

Welcome to Chestnut Knoll, a gated luxury Sonoma residence offering approximately 3,400 sq ft with 3 bedrooms and 3.5 bathrooms, featuring sweeping valley and vineyard views and a private infinity-edge pool and hot tub. Built in 2009, the home blends modern design with high-end finishes, a chef’s kitchen, open living spaces, and seamless indoor-outdoor flow. Set on a 1.24-acre lot just minutes from Sonoma Plaza and world-class wineries, the property also features expansive entertaining areas.

New! The Quails Crossing- Healdsburg Vineyard Home

Brand new modern luxury home designed to maximize the natural beauty & surrounding calm. Perched on a hill surrounded by 100 year old oak trees, this spectacular home was built facing beautiful rolling hills and vineyards with ultimate guest comfort in mind. Enjoy your AM coffee watching a family of quails roaming the vineyard and end your evening with a glass of wine on the deck watching the sun set behind the golden vineyard hills. Located approx 3.5 miles (6min) from the Healdsburg Plaza.

10 Acre Estate with Views, Teahouse, and Picklebal

Discover a private paradise at this 10-acre estate. Surrounded by a hobby vineyard, oak woodlands, and seasonal creeks, this property is a destination in itself. Unwind in the Japanese teahouse, play on the private tennis and pickleball courts, or take in the views from the outdoor patio. The beautifully appointed home features fireplaces, a gourmet kitchen, and a deck overlooking the landscape. It's an unparalleled retreat for relaxation, recreation, and exploring the best of Sonoma County.

Calistoga Mansion - 38 Acres | Lap Pool | Views

Escape to your own private 38-acre luxury retreat in pristine Calistoga wine country, with sweeping vineyard views and resort-style amenities. Designed for up to 16 guests, the estate features a main house over 5,000 sq ft, private guest house, 75-ft lap pool with optional heating, outdoor kitchen and bar, game rooms, serene pond, and so much more. Enjoy exceptional privacy ~20 minutes north of downtown Calistoga perfect for upscale getaways to Napa Valley, Sonoma Valley, or even Healdsburg!

Sonoma Wine Country Estate New

Private yet just several blocks from the historic Sonoma Plaza. Located on the valley floor of Sonoma's Eastside, this modern estate is the epitome of chic Wine Country living. The 4 (can be delivered as 5) bedroom, 4.5 bath main house, just over 5000 SqFt, situated on 4.5 acres, offering stunning vineyard and mountain views 200 year old heritage groves. Interior features include floor-to-ceiling sliding glass doors, oak floors, a temperature-controlled wine room, home office, media room.

Year-Round Heated Pool | Hot Tub | Fire Pit | Lawn

Welcome to Sonoma Valley Villa, your one-of-a-kind wine country oasis in Kenwood. The newly built gated villa overlooking vineyards features all the luxury amenities of a five-star resort. → Year-round heated swimming pool with cover → Spacious hot tub → Cozy outdoor fire pit → Vineyard views for miles → Outdoor kitchen and dining → Chef's kitchen with everything for gourmet meals → Fast wifi → Dedicated office area → Lots of space for everyone Walking distance to Kenwood wineries.

Boho Mod Farmhouse Estate Sonoma Pool Spa Bocce Cl

Nestled on 2.1 acres in the heart of Sonoma, this stunning modern farmhouse—recently remodeled and soon to be featured on Staycation—blends elegance with wine country charm. Lounge by the 50-ft pool, soak in the hot tub, or enjoy the bocce court, redwood grove, and sunset swing. With 4 bedrooms (3 king, 1 queen), 3 baths, a sunroom, and open-concept living, every detail invites relaxation and luxury. Book your stay today! The farmhouse is centrally located btwn Sonoma & Napa Valleys.

Luxury Villa, Pool, Spa, BBQ, By Healdsburg Sonoma

Top 5% of homes, Luxe badge, and guest favorite badge by Airbnb. Welcome to Villa Montage - Brand new, luxury 4br/3.5ba Villa in the heart of Sonoma. Close to Wineries & Healdsburg. An award-winning architecture firm in SF designed the house. ☞ New & modern home ☞ Pool & Spa (Pool heated April-Oct) ☞ Outdoor & Indoor fireplaces ☞ Pool table ☞ BBQ with covered patio and dining table ☞ Chef's kitchen ☞ Baby-friendly (crib, toys, monitor) ☞ Tesla Charger ☞ IG @Villamontage.sonoma

*Specials!* Poolside luxury and family enjoyment.

Discover Sonoma Nest, a luxurious family haven nestled in the heart of Santa Rosa, California. This exquisite 4-bedroom house offers a private pool, hot tub, and stunning mountain views, promising an unforgettable escape. Enjoy the convenience of a fully-equipped kitchen, outdoor seating, and easy access to Wine Country's renowned wineries and family-friendly attractions. Create lasting memories in this idyllic retreat.

Dry Creek Wonderland | Private Farm Estate in Wine

Welcome to our gracious home and honey farm, nestled in the rolling hills of Healdsburg. - 4 bedrooms, 4 bathrooms, sleeps 8 - Open, light-filled living space with seamless indoor-outdoor flow - Fully equipped kitchen and spacious dining area - Outdoor patios with BBQ grill and sweeping countryside views - Unique farmstay experience with educational tours available - Easy access to local wineries and hiking