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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.

Guest favorite
Home in Windsor
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
Jul 30 – Aug 6
$652 per night
Guest favorite
Home in Graton
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
Jan 9 – 16
$406 per night
Guest favorite
Home in Windsor
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.
Mar 31 – Apr 7
$495 per night

Popular amenities for Windsor rentals with a pool

House rentals with a pool

Guest favorite
Home in Occidental
Modern mid-century-inspired, Deer Ranch
Apr 6 – 13
$430 per night
Guest favorite
Home in Santa Rosa
Hot Tub/Heated Pool ~ Walk To Shops & Restaurants!
Apr 26 – May 3
$369 per night
Guest favorite
Home in Glen Ellen
Tuscan Wine Country Villa Sleeps 6
Oct 24 – 31
$945 per night
Guest favorite
Home in Kenwood
Sonoma Vineyard Home With Pool & Stunning Views
Jan 22 – 29
$806 per night
Guest favorite
Home in Glen Ellen
Renowned Vineyard Home with Stunning Views
Oct 31 – Nov 7
$787 per night
Superhost
Home in Santa Rosa
Sonoma County Oasis (pool heated March-November)
Sep 2 – 9
$470 per night
Guest favorite
Home in Sebastopol
Gorgeous West County Sonoma retreat
Mar 1 – 8
$385 per night
Guest favorite
Home in Cazadero
"La Masia" -Stunning! Heated Pool, Spa
Oct 20 – 27
$522 per night
Guest favorite
Home in Sonoma
Sonoma Vineyard House with Pool close to Plaza
Nov 3 – 10
$707 per night
Guest favorite
Home in Santa Rosa
Happy House w/large pool, hot tub & chefs kitchen
Jul 4 – 11
$652 per night
Guest favorite
Home in Glen Ellen
Luxury home, heated spa pool, walk to restaurants
Jan 1 – 8
$658 per night
Guest favorite
Home in Sebastopol
Sebastopol Gem, The Birdhouse. Hottub. Pool. Views
Aug 18 – 25
$318 per night

Condo rentals with a pool

Superhost
Condo in Windsor
Spacious Clean 3 BDRM Condo in Sonoma Wine Country
Apr 28 – May 3
$159 per night
Guest favorite
Condo in Windsor
3BR Worldmark Windsor Santa Rosa Resort Condo
May 26 – Jun 2
$314 per night
Guest favorite
Condo in Windsor
Make This Your Best Vacation Ever - 2 Bdrm Condo
Dec 30 – Jan 6
$236 per night
Guest favorite
Condo in Windsor
2BR with Resort Amenities, Hot Tub, Pool, BBQ
Jun 3 – 10
$292 per night
Guest favorite
Condo in Windsor
Great Wine Country and Golfing Resort Getaway!!
Dec 2 – 9
$221 per night
Superhost
Condo in Windsor
Windsor Resort 2bdr Queen
Jun 19 – 26
$266 per night
Superhost
Condo in Windsor
Worldmark Windsor/Santa Rosa Wine Country Resort
Jan 21 – 28
$258 per night
Superhost
Condo in Windsor
Wine Country, CA, 3-Bedroom Z #1
Apr 14 – 19
$213 per night
Superhost
Condo in Windsor
Windsor, CA, 1 Bedroom #2
Apr 13 – 20
$176 per night
Condo in Santa Rosa
Beautiful Downtown 1-BD Sanctuary Home!
Jul 24 – 31
$249 per night
Guest favorite
Condo in Windsor
WorldMark Windsor, CA
Nov 26 – Dec 3
$240 per night
Guest favorite
Condo in Windsor
3bdm-condo Windsor-WorldMark Resort
May 5 – 12
$407 per night

Home rentals with a private pool

Guest favorite
Home in Sonoma
Family Home - Heated Pool, Hot Tub, bikes, firepit
Aug 31 – Sep 7
$811 per night
Guest favorite
Home in Sonoma
Eclectic Hideaway with Backyard Pool & Hot Tub
May 30 – Jun 6
$543 per night
Guest favorite
Home in Guerneville
Riverside Lodge House in Guerneville
Nov 6 – 13
$543 per night
Home in Guerneville
Lovely and Spacious Ranch-Style Home With a Poolside Oasis
Sep 12 – 19
$480 per night

Quick stats about vacation rentals with a pool in Windsor

Total rentals

230 properties

Rentals with dedicated workspaces

90 properties have a dedicated workspace

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

180 properties are a good fit for families

Total number of reviews

3.5K reviews

Nightly prices starting at

$30 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. California
  4. Sonoma County
  5. Windsor
  6. Rentals with pools