Vacation rentals with a pool in Guerneville

Villa Annadel - Stunning 5 Bedroom with a Pool

Escape to your own private sanctuary at Villa Annadel. Savor the unparalleled privacy and modern sophistication of this one-of-a-kind wine country retreat. The expansive 3,200 square foot villa sits on just under 1.5 acres of privacy with a large sparkling pool, hot tub and outdoor dining gazebo. Game lovers will rejoice, from cornhole, to darts, ping pong and vintage arcade games. It’s easy to forget you are minutes from some of Santa Rosa’s finest restaurants and wine tasting destinations!

Modern Log Cabin w/ Pool, Spa & FP Near DT & River

Sunny fully fenced modern log cabin, 3BR/2BA with private pool and SPA in a quiet neighborhood. Surrounded by 380 degrees of lush trees, allowing peaceful tranquility. Impeccably maintained, well-appointed, newly refurbished interior exudes comfort and style. Rich wood flooring throughout, combined with gas fireplace, central air + heat supports absolute comfort. One mile walking distance from downtown Guerneville, the river, restaurants, bars and wineries. 2-Car attached garage ToT#4148

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. SVR25-100

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

Riverside Lodge House in Guerneville

This bright home dazzles with stylish mid-century furnishings sourced from local antique shops and a brick-fronted fireplace. Prep meals in a warm kitchen to serve at a robust hardwood table; cookout on the private decked patio; enjoy a swim in the separately fenced-in pool (shared with the home next door). Pets are welcome! Enjoy walks on the longest stretch of beach in Guerneville across the street from the house and swim with the neighbors who enjoy the public river access.

Wine Country Retreat | Pool, Hot Tub + Vibes

Summer-ready backyard + hot tub | Close to wineries Welcome to Happy House, a comfortable, clean, and welcoming home—perfect for a Sonoma County getaway any time of year. Ideal for wine tasting, visiting local breweries, hiking, mountain biking, plus weekend escapes, or remote work. 🌿 Private Backyard Large yard with pool, hot tub, and easy parking. 🍽 Fully Stocked Chef’s Kitchen 🛋 Seasonal note: Outdoor cushions/umbrellas stored late Oct–mid May. Permit # SVR25-160

Private Resort with Pool, Pool House, View and Spa

This wine country luxury retreat is a perfect venue for a family or small group escape. Includes a 2 level main house with 3 bedrooms, a large pool, hot tub and separate pool house. Plus wine cellar/game room, work area, family room, gourmet kitchen, five gorgeous stone fireplaces, and a patio kitchen with a gas range & dining area. This beautiful property feels like your own private resort, set on nearly 4 acres including gardens and spectacular views of Mt St Helena.

Heated Pool·Spa·Fire Pit·6 Beds·10 Min to Wineries

Escape to Wine Country with your own heated pool, hot tub, and space designed for gathering. Spend your days wine tasting, then come home to soak, grill, and unwind under the stars. This bright, modern retreat is built for groups, with a fire pit patio, game-filled pool house, fully stocked chef’s kitchen, and plenty of room to relax together. Located just minutes from Sonoma’s top wineries, it’s the perfect home base for a wine weekend.

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

- Luxurious west Sonoma oasis - Heated pool with large wooden deck - 6-person Private Hot Tub - Entertain and feast in the outdoor kitchen with BBQ, Neopolitan Wood-fired Pizza Oven and large outdoor tables. - Newly remodeled farmhouse kitchen - Epic Entertainment Barn: Air Hockey, 100" TV Projector, Darts & More - Expansive backyard with Apple Orchard - Pick Seasonal Vegetables from Garden Beds - Pet Friendly Home, Fenced

Gorgeous Sonoma retreat (with pickleball!)

You'll love the incredible views, fully stocked chef's kitchen, 3,000 sq ft deck, heated pool, pickleball court and lush gardens. Located near loads of wineries, the Russian River and 75 mins to San Francisco. We have blazing fast internet with mesh wifi, large screen TVs throughout the house and an EV charger. We also have various supplies to support your corporate retreat.

Serene Wine Country Retreat with Pool & Hot Tub

Relax and enjoy the best that Sonoma wine country has to offer all year long in this serene retreat with pool and hot tub. Country setting and secluded feel, yet close to dozens of wineries and activities. Short, scenic drive to central Sebastopol or Healdsburg.