Vacation rentals with a pool in Madison
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Madison
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Madison rentals with a pool
House rentals with a pool
Home in Galena
4.93 out of 5 average rating, 122 reviewsThe Beauty on Belden: minutes from amenities!
Dec 15 – 22
Home in Galena
4.97 out of 5 average rating, 101 reviewsMajor reno, photos coming! Hot tub, views, 6BR/6BA
Mar 6 – 13
Home in Galena
4.93 out of 5 average rating, 107 reviewsAwesome Lodge in Galena Territory
Jun 12 – 19
Home in Galena
4.82 out of 5 average rating, 277 reviewsGalena Retreat - Eagle Ridge Territories
Apr 10 – 17
Home in Galena
4.92 out of 5 average rating, 185 reviewsGalena Getaway
May 7 – 14
Home in Galena
4.96 out of 5 average rating, 243 reviewsComfortable 4 Bed 4 Bath in the Galena Territory!
Mar 30 – Apr 6
Home in Galena
4.97 out of 5 average rating, 125 reviewsGalena Territory Sun-Drenched TreeHouse w/ Views
Jun 12 – 19
Home in Galena
4.97 out of 5 average rating, 125 reviewsHot tub/Game Room/Fire Pit/Across street from Pool
Feb 2 – 9
Condo rentals with a pool
Condo in Wisconsin Dells
4.83 out of 5 average rating, 183 reviews❀❀❀ LAKEFRONT CONDO ❀❀❀ Private Pool & Beach
Apr 12 – 19
Condo in Lake Geneva
4.82 out of 5 average rating, 22 reviewsStay Awhile- Historic Hayloft Lodge
Apr 2 – 9
Condo in Lake Geneva
4.98 out of 5 average rating, 82 reviewsMagnificient views in a Lakefront condo, Fireplace
Oct 31 – Nov 7
Condo in Wisconsin Dells
4.92 out of 5 average rating, 25 reviewsUpper Dells River Walk [1BR]
Sep 6 – 13
Condo in Lake Geneva
4.83 out of 5 average rating, 12 reviewsCondo in Geneva with lake views!
Dec 19 – 26
Condo in Wisconsin Dells
4.99 out of 5 average rating, 92 reviewsThe Wanderlust at the Sunset Cove
Nov 8 – 15
Condo in Geneva
4.92 out of 5 average rating, 25 reviewsQuaint, quiet condo minutes from Lake Geneva
Dec 3 – 10
Condo in Lake Geneva
4.95 out of 5 average rating, 44 reviewsCozy Lake Geneva Retreat with Year-Round Views!
Apr 24 – May 1
Quick stats about vacation rentals with a pool in Madison
Total rentals
40 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
580 reviews
Nightly prices starting at
$10 before taxes and fees
Destinations to explore
- Milwaukee Vacation rentals
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