
Vacation rentals with a pool in Windsor
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Top-rated rentals with a pool in Windsor
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Farpoint: Heated Infinity Pool, Mountain Views
Nestled in the Mayacamas mountains, this elevated home offers a peaceful and luxurious retreat in the center of Sonoma wine country. The large infinity pool - gas-heated all year - perches over the magnificent view. Inside, the living room and dining room are furnished to comfortably seat 12 adults. A pool table, ping pong, three dining tables, 75" 4K TV, and large hot tub provide endless options. Hiking trails surround the house. Grocery stores and farmer’s markets are less than 8 minutes away.

Tropical Oasis with Pool & Hot Tub 30min to Sonoma
This tropical oasis is located right in the heart of wine country, featuring 4 bedrooms, 4 full bathrooms, an in-ground pool, hot tub, waterfall with a fire pit, beautiful fireplace in the living room, and an open floor plan perfect for spending time with family and friends. Located just down the road from Anadell State park and the local Bennet Valley golf course; just minutes to downtown Santa Rosa featuring restaurants, bars, shopping and more. Only 30 min to Sonoma and 20 min to Healdsburg.

Wine Country | Pool & Spa | Park Views | Fast WiFi
Your home base for Sonoma, Napa, the Russian River and Sonoma Coast! A quiet neighborhood home within easy walking distance to shops and restaurants with many more options just a short drive away. Hundreds of wineries, breweries, and distilleries are here. Dozens of state and regional parks are waiting for you to explore. There's even a great neighborhood park just behind the house! Wondering what to do on your visit? My co-host Brenna and I are happy to help plan your trip to Wine Country.

Pacific Gardens Retreat
Enjoy a tranquil art filled garden escape at our pet friendly home! Whether you are soaking in the hot tub after a day of wine tasting or having dinner with friends this indoor/outdoor living retreat will leave you feeling relaxed. Well stocked kitchen, fast wifi and walking distance to downtown. Great restaurants and breweries nearby. Well behaved non destructive pets are welcome in this home. It may not be a fit if you have severe allergies though we do our best to clean very thoroughly.

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

Happy House Getaway - Pool, Hot Tub & Wine Country
Happy House – Year-Round Sonoma County Getaway with Pool & Hot Tub 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

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.

Pool + 4 Hot Tubs! Gym, Luxury 2 bedroom villa.
Two Bedroom Twins: King in master, twins in second bedroom, queen Murphy bed in living area. Maximum occupancy 6. Full Kitchen: Unit includes refrigerator, sink, range and dishwasher. Resort has Pool, Children's Pool, Hot Tub, and much more. ❤ Free Parking. Free Internet ❤ ★ If reserving a FRIDAY OR SATURDAY there is a 2 night minimum unless request is made last minute (3 days before check in)★ ★24 hour reception★ ★Calendars updated daily★ ★Multiple Units/Room Sizes Available★

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

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.

Nice home, wineries, heated pool, hottub fire pit
This newly remodeled home is your perfect vacation rental. It features a heated pool for you to enjoy year round! There is also a brand new hot tub for an extra dose of relaxation. Enjoy your meal outside around the fire pit table or in the large open kitchen area of the home. If you want a little more privacy, there is an additional side yard with its own fire pit for you to sneak away to. With its prime location (only 20 min to Sonoma) this is the Wine Country home for you!

Luxury home (+ pool house) with views, pool & 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.
Popular amenities for Windsor rentals with a pool
House rentals with a pool

Sonoma Country Club Wine Country w/ pool

Vineyard-House Escape in Sonoma Wine Country

Eclectic Hideaway with Backyard Pool & Hot Tub

STAY AWHiLE Hot Tub Walk 2 Guerneville Yard

Nice Wine Country Family Home

Serene Wine Country Retreat with Pool & Hot Tub

Large Charming Home Surrounded by a Vineyard

Riverside Lodge House in Guerneville
Condo rentals with a pool

WorldMark Windsor, CA

Windsor Deluxe Resort 1bdr

Santa Rosa - Self Contained Suite 5 Mins Away

2 Separate 3BR Apts with Resort Amenities

1 BR Worldmark Windsor Resort Condo Wine Country

Sip, Taste, Hot Tub - Repeat - 2 Bdrm Condo-Slps 6

Windsor, CA. - Windsor Resort - 3-Bd

Resort Living w/ Pools - 2 Bdm Condo Slps 6
Other vacation rentals with a pool

Wine Country Retreat w/ Private Pool - Sleeps 8

Luxurious 3-Bedroom Home in Healdsburg

Windsor, CA, 1-bedroom #2

Adventures surround this charming 2bedroom home.

Wolf Ridge Sonoma Mountain Retreat

Modern Barn Nestled in the Countryside

MidCentury Modern Wine Country Private Pool & Spa

Sonoma Wine Country Home: Pool, Hot Tub & Fun!
When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R3,448 ZAR | R3,364 ZAR | R3,364 ZAR | R3,347 ZAR | R3,415 ZAR | R3,717 ZAR | R3,633 ZAR | R3,499 ZAR | R3,347 ZAR | R3,499 ZAR | R3,650 ZAR | R3,684 ZAR |
| Avg. temp | 10°C | 10°C | 11°C | 11°C | 12°C | 13°C | 14°C | 14°C | 15°C | 13°C | 12°C | 10°C |
Quick stats about vacation rentals with a pool in Windsor

Total vacation rentals
Explore 260 vacation rentals in Windsor

Nightly prices starting at
Windsor vacation rentals start at R841 ZAR per night before taxes and fees

Verified guest reviews
Over 4,130 verified reviews to help you choose

Family-friendly vacation rentals
210 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wi-Fi availability
260 of Windsor vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Windsor rentals

4.9 Average rating
Windsor stays are highly rated by guests—averaging 4.9 out of 5!
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- Lake Berryessa
- Muir Woods National Monument
- Six Flags Discovery Kingdom
- Jenner Beach
- Bolinas Beach
- Goat Rock Beach
- Doran Beach
- Safari West
- Johnson's Beach
- Sonoma Coast State Park
- Limantour Beach
- Trione-Annadel State Park
- Chateau St. Jean
- Armstrong Redwoods State Natural Reserve
- V. Sattui Winery
- Jack London State Historic Park
- Charles M. Schulz Museum
- Napa Valley Wine Train Wine Shop
- Mount Tamalpais State Park
- Sugarloaf Ridge State Park
- Harbin Hot Springs
- Iron Horse Vineyards
- Healdsburg Plaza
- Salt Point State Park




