Holiday rentals with a pool in Windsor
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Windsor
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Windsor rentals with a pool
House rentals with a pool
Home in Kenwood
4.99 out of 5 average rating, 271 reviewsSonoma Vineyard Home With Pool & Stunning Views
21–28 Mar
Home in Sebastopol
4.98 out of 5 average rating, 150 reviewsSebastopol Gem, The Birdhouse. Hottub. Pool. Views
6–13 Mar
Home in Santa Rosa
4.87 out of 5 average rating, 164 reviewsHot Tub/Heated Pool ~ Walk To Shops & Restaurants
29 Jul – 5 Aug
Home in Santa Rosa
4.9 out of 5 average rating, 109 reviewsSonoma County Oasis with Heated Pool
8–15 Jan
Home in Sonoma
4.94 out of 5 average rating, 428 reviewsThornsberry House, A Luxe Country Getaway
15–20 Jun
Home in Cazadero
4.95 out of 5 average rating, 183 reviews"La Masia" -Stunning! Heated Pool, Spa
13–20 Oct
Home in Forestville
4.87 out of 5 average rating, 265 reviewsHazels Hideaway Hot Tub Redwoods Bonus Room
17–24 Jul
Home in Glen Ellen
4.96 out of 5 average rating, 173 reviewsTop 5%. Renowned Vineyard Home. Near Wineries
7–14 Nov
Apartment rentals with a pool
Apartment in Windsor
5.0 out of 5 average rating, 5 reviewsSpacious Clean 3 BDRM Condo in Sonoma Wine Country
12–17 May
Apartment in Windsor
4.94 out of 5 average rating, 16 reviewsWindsor Santa Rosa Resort Condo 3BR Open Pool Nice
29 Jul – 5 Aug
Apartment in Windsor
4.93 out of 5 average rating, 44 reviewsMake This Your Best Vacation Ever - 2 Bdrm Condo
19–26 Apr
Apartment in Windsor
4.93 out of 5 average rating, 70 reviewsGreat Wine Country and Golfing Resort Getaway!!
4–11 Apr
Apartment in Windsor
4.94 out of 5 average rating, 17 reviews2BR with Resort Amenities, Hot Tub, Pool, BBQ
4–11 Mar
Apartment in Santa Rosa
4.86 out of 5 average rating, 49 reviewsBeautiful Downtown 1-BD Sanctuary Home!
3–10 Jun
Apartment in Windsor
4.84 out of 5 average rating, 19 reviewsWorldmark Windsor/Santa Rosa Wine Country Resort
25 Nov – 2 Dec
Apartment in Windsor
Windsor Deluxe Resort 2bdr
19–26 Jul
Home rentals with a private pool
Home in Sonoma
4.82 out of 5 average rating, 346 reviewsFamily Home - Heated Pool, Hot Tub, bikes, firepit
11–18 Aug
Home in Sonoma
4.93 out of 5 average rating, 240 reviewsEclectic Hideaway with Backyard Pool & Hot Tub
16–23 Oct
Home in Guerneville
4.91 out of 5 average rating, 162 reviewsRiverside Lodge House in Guerneville
11–18 Oct
Home in Guerneville
4.83 out of 5 average rating, 160 reviewsLovely and Spacious Ranch-Style Home With a Poolside Oasis
19–26 Nov
Quick stats about holiday 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
$41 SGD before taxes and fees
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