
Holiday rentals with a pool in Wine Country
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Wine Country
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Award-Winning Forest Getaway: @thesearanchhouse
**Recently refreshed/re-furnished!** This house was named 'The Ranch House' by its architect Don Jacobs, this updated 70s cabin is a forest getaway with modern sensibility. The house is surrounded by redwoods & has 2 large decks, 1 w/ propane firepit w/ ample seating, the other w/ hot tub. Living room has picture windows w/ forest views & Morso wood-burning stove. Guests are encouraged to enjoy the hiking trails, pools, and outdoor amenities. House comfortably sleeps 4, plus fiber-optic internet

Designer Sonoma Getaway with Pool, Hot Tub & Bocce
Thornsberry House is a luxe Wine Country home nestled between the two oldest wineries in California while just 5 minutes from the Sonoma Square. Renovated to accommodate the most discerning traveler, it consists of two separate buildings connected by a breezeway and large deck. Situated on the east side of town, it offers a true escape where one can walk or bike down to Gundlach Bundschu at the end of our street, or soak up the afternoon light from the heated pool, hot tub or a game of bocce.

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!

Unique Stay! Pool/ Hot tub/ Game Room/ Bar/ Views
This 3,700 sqft open floor plan home will leave you awestruck the minute you enter. This home was constructed using old-growth timber from the Fort Bragg bridges and the Potter Valley Lumber Mill, with over 1,300 linear feet of large timber mixed with patina sheet metal and 36' high ceilings. It features an arched bridge spanning over 20' across open air space to access the master bedroom. The home also offers a 40,000 gallons deep water swimming pool, hot tub, gas fire pit, and a large bar.

Design & Style with White Water View
A truly one-of-a-kind, stylish retreat with unobstructed, cliffside Pacific views and all the comforts of a boutique hotel. Located in historic Condo Unit 2 and designed by the original architects, Moore Lyndon Turnbull Whitaker. The home sits adjacent to The Sea Ranch Lodge, with direct access to 10 miles of coastal trails & all The Sea Ranch amenities . It has been thoroughly updated with today's convenience and comfort in mind. Unwind, unplug, relax in this unique paradise on the coast.

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

Private and spacious redwoods retreat at Sea Ranch
Tucked away in the redwoods, this newly furnished home is a serene retreat at Sea Ranch. It enjoys near-total privacy on three acres of forest, plus the sound, smell and sight of the ocean through a gap in the trees on a clear day. The main room and the master bedroom are spacious, with views of the forest from every angle. The house has fiber-optic internet and has sufficient space for two people to work remotely very comfortably. More pictures on IG: @theseaforesthouse. TOT 3398N.

ROSEA Ranch: cozy, oceanfront, walk to beach
Located steps from premier sand beach, Walk on Beach. Entering the gates, you'll be greeted by a tranquil, mature garden blocked from the wind, a deck, and a hot tub. Inside this solar powered 1970s modern vernacular contemporary home, you'll find a cozy raised living room positioned for maximum views. Bedrooms are on the ground floor, along with bathrooms, living, dining, fully-equipped kitchen, and laundry. A study is upstairs. 1% of proceeds go to airbnb.org

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.

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

Panoramic OceanViews Dog Friendly SeaRanch Retreat
Wake up above the coastline to sweeping, unobstructed Pacific Ocean views that guests say “pictures simply can’t capture.” Located on a quiet hillside, this serene 2-bedroom, 2-bath retreat offers dramatic views and direct access to miles of scenic trails.

Ocean Front with Pool on Wild Sonoma Coast
The Cove House in Timber Cove offers a dramatic and romantic experience you will savor for a lifetime. Intimate enough for the honeymoon of your dreams yet spacious enough for two couples. White water forever views, large spa and bluff top pool.
Popular amenities for Wine Country rentals with a pool
House rentals with a pool

Farmhouse at Sonoma Oaks: Hot Tub · Pool · Bocce!

Casa Del Mar, Spectacular Ocean Views!

Coastal Modern Retreat w/ Hot tub

Vineyard-House Escape in Sonoma Wine Country

The Bluffs at Sea Ranch - Expansive Ocean Views

Seaward Bliss ★ (Private Hillside Retreat)

Wine Country Retreat | Pool, Hot Tub + Vibes

Balina: ocean views, hot tub, pets OK, remodeled
Apartment rentals with a pool

Wine Country Living at it's best at Silverado CC

Fairways Silverado Golf and Country

1 bed | 1 bath | Silverado Resort Experience

Your wine and wellness retreat at Silverado Resort

Bright Napa Condo • Pool View + 10min to DT

Beautiful Premium Jr Suite, Silverado Resort & Spa

Silverado Resort Condo with Pool

2 bed I Silverado Resort & Spa in Napa - Wine Town
Other holiday rentals with a pool

Luxury Container Home w Infinity Pool + 360 Views

707 BARREL LOUNGE Cottage

Sea Ranch Forest Retreat with Ocean Views

Owl House - Hideaway Sanctuary

Jago Bay - Vineyard Home with Pool and Hot Tub

Fir Wood – Original Sea Ranch Cluster House

ALBA | A modern luxury retreat in Healdsburg

La Cava -Valley of the Moon
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- Jenner Beach
- Goat Rock Beach
- Doran Beach
- Johnson's Beach
- Safari West
- Trione-Annadel State Park
- Sonoma Coast State Park
- Armstrong Redwoods State Natural Reserve
- V. Sattui Winery
- Ledson Winery & Vineyards
- Iron Horse Vineyards
- Charles M. Schulz Museum
- Sugarloaf Ridge State Park
- VJB Vineyard & Cellars
- Chateau St. Jean
- Sonoma State University
- Salt Point State Park
- Healdsburg Plaza
- Harbin Hot Springs
- Francis Ford Coppola Winery
- Bodega Head
- Mendocino National Forest
- Howarth Park
- St. Francis Winery and Vineyard
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