Vacation rentals with a pool in Healdsburg

Pool•Spa•6 Bikes•1mi to Town•Fire Pit•ShuffleBoard

This beautifully designed 3bd/2bth luxury home is bursting with resort-like amenities to ensure your stay is relaxing & fun. Comfortably sleeps 8, incl. a pull-out couch in a private bonus room - 1mi - Dwntwn Healdsburg & 20+ wineries. - Pool & Hot Tub - Lush 3/4 acre lot w/20+ orchard trees - 6 Adults Bikes - Shuffle Board, Outdoor Giant Chess & Jenga, Croquet, Ping Pong - Outdoor Dining, BBQ, Lounge Seating, Fire Pit - Pac N Play & High Chair - 3 Smart TV's -Netflix/Disney+ - Pet friendly

Luxe WineCountry getaway with Pool, hottub & Bocce

Thornsberry House is a luxe Wine Country home nestled between the 2 oldest wineries in California and just minutes from the Sonoma Square. It is renovated with a boutique hotel feel to accommodate the most discerning traveler. It consists of 2 separate buildings with 3 bedrooms, connected by a breezeway and large deck with a heated pool, hot tub and bocce. Situated on the east side of town, it is in short equal distance to Buena Vista and Gundlach Bundschu, the 2 oldest wineries in California.

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

Vineyard Retreat • Steps to Tastings • Press Pick

WHY YOU'LL LOVE IT -Stroll through your own private vineyard -Pool, hot tub & bocce in a stunning serene setting -Minutes to top wineries, restaurants spas & towns -Complimentary tastings at the Estate Winery next door -Stylish interior with thoughtful touches -Chef-ready fully stocked kitchen -Helpful host and quick communication AS FEATURED IN Condé Nast Traveler | House Beautiful | House & Garden | The Wine Daily | Esquire | The Bold Italic | Refinery 29| Bon Traveler | Sunset Magazine

The Deer Retreat – Privacy and Comfort

At the end of a private road (recently redone), the Deer Retreat offers privacy to enjoy the newly renovated pool, the hot tub, and the full outdoor kitchen. With sprawling views of a large private backyard, you will be sure to spot some deers or wild turkeys who call this peaceful place home. When staying inside, you will enjoy the privacy of the 2 large en-suite master bedrooms which are located at opposite ends of the house, or regroup in the large vaulted living room with open kitchen.

Wing in Tuscan Villa with Vineyard and two bedrms

Beautiful Tuscan-inspired villa perched at the northern most corner of Alexander Valley and Sonoma County. Perfect abode to escape the city and experience the beautiful outdoors with luxurious amenities. Cloverdale, Healdsburg & Anderson Valley Wineries all within short drive on Highway 128 wine trail - 1 hour’s drive to coast and town of Mendocino. Modern private space with full kitchen and private bathroom with access to pool, jacuzzi, outdoor kitchen/grill, and fire pit. TOT# 2713N

Sonoma Wine Country Estate Guest House

Are you intrigued by the historical 1917 Crane Canyon Estate in Sonoma Wine Country with the prohibition-era speakeasy and tales of grand Gatsby-like parties?... Or the incredible panoramic views of Sonoma Wine Country?... Or the generous hosts who'll happily point you to the best off-the-beaten-path Sonoma and Napa county treasures... (or just as happily stay out of your way ;) ?... TAKE A BREAK FROM LIFE. We are here to help you do that. ***We are UNABLE to accommodate SERVICE ANIMALS.

Vineyard Vista, Modern Farmhouse Cottage with Pool

Our architect remodeled (2021), five star, elegant Farmhouse with great room and fireplace, is simply perfect throughout. This unique wine country two-acre property, with heated swimming pool (for a fee), looks out to the beautiful Russian River vineyards and the never-ending Western panorama. Only minutes from award winning food and shopping in downtown Healdsburg, it’s within easy walking or bicycling distance of tasting rooms at J, Rodney Strong and other acclaimed Sonoma wineries.

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

Modern mid-century-inspired, Deer Ranch

Deer Ranch is a remodeled 2 bedroom, 1 bathroom home sitting on four acres of private land, with outdoor decks, hot tub, and plunge pool. This contemporary Frank Lloyd Wright-styled-like home sits on top of a hill with meadows below and towering redwoods that add to a peaceful seclusion getaway, and still only minutes from the hamlet of Occidental (1.3 miles). The pool is open during the summer months only (late May-end of September). The hot tub is on all year-round.

Romantic Tropical Garden Casita

As you step through the entrance and under the arch, you are transformed into another time and place. We have been told by guests they feel it reminds them of Italy, France, and Spain. The Hacienda is very private, behind the walls of the early California style home. The gardens are lush and filled with birds of all kinds. There are several vignettes to relax and watch nature. Nights are cool so there is no need for A/C if you leave window open at night.

Wine Country Luxury Retreat - Pool Sauna Spa Views

Welcome to Sonoma Valley Retreat! The Luxury Mediterranean-inspired resort style house in the middle of a world-class wine country. 3600 Square feet House is located in the world-famous Sonoma Valley and is perfect for all your vacation needs. It's where style and sophistication meets entertainment and fun. Enjoy stunning outdoor amenities; one of a kind round soaking pool private pool with spa, pine wood sauna and breathtaking garden, mountain views