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Vacation rentals with a pool in Healdsburg

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Top-rated rentals with a pool in Healdsburg

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

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Home in Guerneville

4.83 out of 5 average rating, 173 reviews

Lovely and Spacious Ranch-Style Home With a Poolside Oasis

Savor outdoor suppers under a forest skyline in this wine country ranch. A lush, treelined perimeter encloses a shaded patio area featuring furnished terraces, a fire pit, and a central pool. Warm up in the hot tub after an evening swim. The layout of the house is unique. Each section of the house provides its own artistic and cozy energy. You can access the entire house except for the garage. I'm available 24/7 for any questions and needs. Guerneville is a small, rustic community nestled in the Russian River Valley. Sample local varietals at some of the world's finest vineyards or hike into the towering Redwood Forest. The town of Guerneville offers an array of fine local eateries. Please call me when you arrive and I'll walk you through the details of the home and the town!

Home in Glen Ellen

4.96 out of 5 average rating, 173 reviews

Stay on a Vineyard. Great Views & Location

Immerse yourself in a Wine Country experience that has captured the attention of prestigious publications - Condé Nast Traveler - Esquire - House Beautiful - House & Garden - Refinery 29 - The Bold Italic - The Wine Daily - Bon Traveler - Sunset Magazine WHY YOU'LL LOVE IT - Vineyard setting and views - Minutes to award-winning wineries, restaurants & spas - Pool, hot tub, bocce ball court - Fully-stocked kitchen - Ultra high-speed Internet - Complimentary tasting at the Estate Winery next door

Condo in Napa

4.99 out of 5 average rating, 163 reviews

Coastal Condo by Pool: King Bed, Balcony, Kitchen

Come experience a comfortable and relaxing retreat in the amenity-rich Silverado resort community and convenient to Napa Valley attractions. Everything you need is here – from a well-equipped kitchen to cozy bedroom, 2 king beds, fireplace, and balcony overlooking the condominium pool. You’ll enjoy access to resort amenities – restaurants, pool, Tesla charging station, laundry, and more. Guests rave about cleanliness, coastal decor, and responsive host. Launch your wine-country exploration here!

Home in Sonoma

4.82 out of 5 average rating, 366 reviews

Family Home - Heated Pool, Hot Tub, 2 fire places

Pool heated year round. Nov-April by request only. Book w/confidence! Buy trip Insurance! Ask for details. Pets welcome. Melt in the hot tub, cool off in the pool, dine on the deck as the sun sets. Inside, 4 skylights & an open layout give a real sense of space & light. Brew Peet's coffee while listening to songs on the Bose stereo. Bike to town, wineries & restaurants. Enjoy a game of ping pong. Sit under the stars by the fire pit. - 1 pet $100. 2nd pet $50 - signed rental agreement required

Home in Sonoma

5 out of 5 average rating, 140 reviews

Sonoma Vineyard House, Pool Hot Tub near Plaza

Enjoy your own retreat in the middle of the vineyards, yet close to all of downtown Sonoma's charms and conveniences Central location to many wineries & the Sonoma Plaza, but you may never want to leave this tranquil property surrounded by vineyards. *3 bd/2 ba *Gas Fireplace Heat, AC in house and pool house *Pool *HotTub *Fire pit *Multiple lawns and lawn games *Outdoor movie area *Outdoor bbq / dining area *Complimentary Sonoma wine *Includes 4 bikes *Sleeps a total of 8 guests.

Home in Sonoma

4.91 out of 5 average rating, 116 reviews

Spectacular Stone Pool/Spa with Views; Near Plaza

A spectacular stone pool and spa with bubbling stream compliments the warm and welcoming Summers House. (Please see notes below regarding pool and spa fees.) The house exudes charm. Sweeping views reach to the San Francisco Bay. Art, antiques and books create an embracing ambiance. Nestled into three, private wooded acres, Summers House is near wineries, and just 10 minutes from Sonoma Plaza restaurants, shops, and events. Well equipped kitchen, great dining spaces, large deck, comfy beds.

Home in Windsor

4.98 out of 5 average rating, 179 reviews

Luxury Wine Country Estate with pool & hot tub

Welcome to our amazing Wine Country oasis, perfect for your relaxing getaway! This home features a large chef’s kitchen, four spacious bedrooms, and two living rooms. Enjoy the outdoor amenities, including large pool, hot tub, outdoor kitchen, bathroom, and dining area. You can also play a game of pool or pingpong in the finished garage! This home is located close to the Sonoma County Airport, wineries, and world-class dining, making it the perfect choice for enjoying all wine country offers

Home in Santa Rosa

4.86 out of 5 average rating, 200 reviews

Hot Tub/Pool ~ Walk To Wine, Shops & Restaurants

Escape to our Mid Century Modern home in beautiful Sonoma Wine Country, a 10 min drive to some of the best wineries in the world! Relax in the large pool & hot tub, by the Traeger grill for BBQ dinners - where pets are welcome! Walking distance to Howarth Park, Spring Lake, in the neighborhood of Annadel State Park for hiking & biking. One block from Montgomery Village, full of boutique shops & Wine-Country restaurants. A 20 minute drive to Sonoma, & near Healdsburg, Kenwood + Bodega Bay.

Villa in Napa

4.95 out of 5 average rating, 133 reviews

An Italian Villa in the heart of Napa Valley!

Villa RayEl was inspired by the farmhouses and small villas of Italy. Located midway between downtown Napa and Yountville, this property sits on 2 acres providing great privacy. It sits next to a year-round creek with a view of a vineyard and nightly sunsets. It has a pool and an attached hot tub. Located 5 minutes off Highway 29, 8 minutes to Downtown Napa and 8 minutes to Yountville. It is convenient to great wineries, restaurants. Its the perfect getaway for families and friends!

Guesthouse in Santa Rosa

4.88 out of 5 average rating, 156 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.

Home in Glen Ellen

4.92 out of 5 average rating, 166 reviews

Luxury home, heated spa pool, walk to restaurants

Luna Lodge, a 3 bedroom 2 bath Glen Ellen village luxury home in the heart of Sonoma wine country. The home has a beautiful garden with spa pool by a peaceful creek. Everything you need for a great vacation is at your fingertips. Situated on a quiet lane, 5 min walk to wine tasting rooms, top restaurants, food markets. Enjoy a gourmet private chef dinner while at the home. Let us know if you are interested and we will help you arrange a very special dining experience.

Home in Healdsburg

4.91 out of 5 average rating, 106 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, 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.

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Popular amenities for Healdsburg rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Sonoma

5 out of 5 average rating, 7 reviews

Upscale Private Sonoma Wine Country Retreat

Home in Santa Rosa

4.89 out of 5 average rating, 171 reviews

Historic 1880's Craftsman Style Home with Pool.

Home in Sonoma

4.93 out of 5 average rating, 107 reviews

Sonoma Ranch, private pool on 7 acres!

Home in Kenwood

5 out of 5 average rating, 16 reviews

[Egg Farm Ranch] Heated Pool-Water Slide-Hot Tub

Home in Guerneville

4.83 out of 5 average rating, 159 reviews

STAY AWHiLE: Hot Tub *Pool through 10/14

Home in Santa Rosa

4.96 out of 5 average rating, 175 reviews

Happy House w/large pool, hot tub & chefs kitchen

Home in Santa Rosa

4.98 out of 5 average rating, 103 reviews

Sonoma Green House *Pool*Close to Wine Country

Home in Sonoma

4.93 out of 5 average rating, 230 reviews

4BD House with Pool, Close to Sonoma Plaza

Condo rentals with a pool

Condo in Napa

4.96 out of 5 average rating, 135 reviews

Silverado Resort Dual Suite golf course villa

Condo in Napa

4.85 out of 5 average rating, 95 reviews

Silverado Mansion Junior Suite | Pool | 1Bd | 1Ba

Condo in Windsor

5 out of 5 average rating, 3 reviews

Spacious 2 BDRM Condo in Sonoma Wine County

Condo in Windsor

4.84 out of 5 average rating, 32 reviews

Wine Country 2 Bdrm Condo w/ Pools & Hot Tubs

Condo in Napa

4.92 out of 5 average rating, 71 reviews

Silverado Resort - Private 3 Bedroom, 2 Bath Condo

Condo in Napa

4.98 out of 5 average rating, 218 reviews

Gorgeous Napa Getaway

Condo in Napa

5 out of 5 average rating, 11 reviews

Perfect Golf course view at Silverado resort

Condo in Napa

4.93 out of 5 average rating, 102 reviews

Fairways Silverado Golf and Country

Quick stats about vacation rentals with a pool in Healdsburg

Total rentals
20 properties
Nightly prices starting at
$100 before taxes and fees
Total number of reviews
400 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

Destinations to explore