Vacation rentals with a pool in Geyserville

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Top-rated rentals with a pool in Geyserville

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

A modern home is showcased with large sliding glass doors that open to a spacious wooden deck. The inviting heated pool features a gentle curve, with sun loungers placed nearby. Lush greenery surrounds the property, enhancing the tranquil outdoor setting.

Home in Sonoma

4.95 out of 5 average rating, 498 reviews

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.

Top guest favorite

A serene pool area is framed by natural stone paving, with a wooden pergola enhancing the outdoor space. Lush greenery and shrubs provide a backdrop, while distant rolling hills can be seen in the background, adding to the scenic tranquility.

Guest suite in Healdsburg

4.93 out of 5 average rating, 456 reviews

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

Guest favorite

Guesthouse in Cloverdale

4.94 out of 5 average rating, 236 reviews

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

Top guest favorite

Home in Healdsburg

4.91 out of 5 average rating, 117 reviews

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.

Top guest favorite

A private pool area features a refreshing swimming pool surrounded by natural landscaping. A float is seen in the water, while the stand-alone home with large windows provides a charming backdrop. Potted plants add greenery to the serene outdoor space.

Home in Graton

5 out of 5 average rating, 671 reviews

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

Superhost

A bottle of Korbel champagne is displayed on a red placemat alongside two clear champagne flutes. The background reveals a cozy living area with a bright sofa and warm lighting, creating an inviting ambiance.

Cottage in Rio Nido

4.86 out of 5 average rating, 698 reviews

Name'Stay - A Peaceful Zen Retreat

Welcome to Nama'Stay. One of the most sought out rentals in the Russian River area, for a good reason. Featuring fastest local Internet available. Low cleaning fee and minimal check-out requirements. Located steps away from the Rio Nido Roadhouse resort. Immediate neighbor to Korbel. Just 1.25 miles from downtown Guerneville. Perfect for a couple, or group up to 4. Modern and renovated 2BD with Private hot tub. Professionally cleaned and managed. Fully stocked with amenities.

Guest favorite

A swimming pool is featured with a bright blue surface, reflecting the surrounding greenery. A set of steps leads into the pool, and a diving board is positioned at the edge, providing an inviting space for relaxation and enjoyment.

Guesthouse in Santa Rosa

4.89 out of 5 average rating, 195 reviews

2 Wine Country Gem 2 Bedroom Upstairs

Looking for a place to stay in Santa Rosa that offers comfort, convenience, and charm? Look no further than our cozy guest house, located in a private gated property. You’ll have your own entrance and access to a shared laundry room with supplies. Enjoy the use of our pool, barbeque, and outdoor kitchen and seating area, where you can relax and soak up the sun. And as a special treat, you’ll get to savor our private tiffin service that delivers delicious home-cooked meals too.

Guest favorite

An outdoor space features a plunge pool surrounded by a sun deck with lounge chairs and a sun umbrella. The home, with its wood accents, is set against a backdrop of tall redwood trees, contributing to a serene, natural setting.

Home in Occidental

4.95 out of 5 average rating, 163 reviews

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.

Top guest favorite

A private pool area is depicted, featuring a spacious pool with a water slide. Sheltered by trees, lounge chairs and a small dining set are positioned nearby. A hot tub is visible, providing a relaxing atmosphere for guests. Shade is offered by surrounding foliage.

Home in Clearlake Oaks

4.97 out of 5 average rating, 115 reviews

Private pool, Hot tub, lakeview w/family & friends

Relax with the whole family or friends at this peaceful private unique place to stay. Have fun or just enjoy quiet time. Swim or hang by the pool or hot tub. BBQ or cook in the kitchen and eat while you look at the lake view! There are smart phone jacks in each room, plenty of parking, a private fenced in yard and screen room. This property has all the added modern comforts of a forced air heating and cooling system, washer/dryer and safe play area for the kids!!

Top guest favorite

Home in Santa Rosa

4.97 out of 5 average rating, 207 reviews

Happy House Getaway - Pool, Hot Tub & Wine Country

Welcome to Your Relaxing Getaway! My home is a comfortable, clean, and happy space—perfect for unwinding and enjoying all that Sonoma County and the Bay Area have to offer. 🌿 Spacious Backyard: Large yard with a pool (heated by the sun) 6-person hot tub (kept at 102°F) Easy parking 🍽 Fully Stocked Chef’s Kitchen 🛋 Seasonal Note: Outdoor cushions/umbrellas stored late Oct to mid-May Come stay—you’ll love it! Happy House Permit #: SVR24-194

Top guest favorite

A modern cottage is set against a backdrop of vibrant landscaping, showcasing a large, clear salt-water pool. Various outdoor seating areas are visible, complemented by lush trees and greenery that enhance the serene environment.

Guesthouse in Sonoma

4.95 out of 5 average rating, 268 reviews

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

Top guest favorite

An outdoor dining area is set with plates and glasses, surrounded by a shaded umbrella. The private pool is visible in the background, complemented by sun loungers and lush greenery. A decorative pot adds an inviting touch to the tranquil environment.

Home in Windsor

4.93 out of 5 average rating, 169 reviews

Luxurious home and pool

Beautiful executive home loaded with sophisticated upgrades. This spacious open floor plan features 4 bedrooms, 3 baths, and a private pool with a fountain. The gourmet kitchen, hardwood floors, and granite counters are all part of the great room with fireplace. Centrally located in Sonoma county with more than 20 wineries within a 10 minute drive. This house is just 5 miles from Healdsburg and 20 miles from Calistoga.