Holiday rentals with a pool in Healdsburg

Luxury Container Home w Infinity Pool + 360 Views

Enjoy the sounds of nature from your own private 12 acre oasis in this unique container home. Set on a private road, and built on a ridge with incredible 360-degree panoramic views from sunrise to sunset, this modern dwelling has been thoughtfully crafted with simplicity and indoor-outdoor living at the forefront of design. From the valley views to the distant mountains, every room feels a part of nature. Enjoy your private oasis from the infinity pool and spa, w views overlooking wine country.

Private Charming Poolside 1 BD/BA in Sonoma Valley

Escape to your home-away-from-home on a private residential compound: the perfect getaway spot in the heart of beautiful Sonoma Valley! 🏡 Why You’ll Love It: ✔️ Minutes to 25+ wineries & great restaurants ✔️ Easy drives to Sonoma, Calistoga, Healdsburg, Napa & the Coast ✔️ Great hiking in nearby parks ✔️ Birdwatching in the garden ✔️ Saltwater pool & bocce court ✔️ Stunning Mountain views ✔️ Private patio with gas grill & outdoor dining ✔️ Full kitchen, separate bedroom with ensuite bath

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

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

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 covid 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.

Forest View Ranch Suite and Treehouse with Pool

Escape to our historic 80-acre ranch, this is not simply an overnight stay! Imagine a tranquil, breathtaking experience on a ranch in a redwood valley. Enjoy exclusive access to ranch amenities. Pool, Fire pits, Apple Juicing, Private Hiking Trails, Outdoor Bathtubs and Shower, Treefort, Seasonal Creek, Outdoor Kitchens, Canoe/Kayak Trips, Russian River Floats, Jeep treks, Private chef experience or cooking classes, Private yoga classes, Massage, Archery, and more!

Wine Country Gem - Sonoma Cottage with Pool Oasis

Charming Sonoma cottage perfect for a romantic getaway, girls’ trip, or family stay. Explore Sonoma, Glen Ellen & Napa with ease. The private unit has gourmet appliances, a minimalist-country style, and its own deck with dining + lounge seating. The peaceful 1-acre property features vineyards, a large saltwater pool, a veggie + herb garden, and fruit trees. Relax, recharge, and enjoy the best of wine country living. TOT #3140N