
Holiday 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.
Holiday 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 Middleton
4.92 out of 5 average rating, 38 reviewsSunny contemporary home with pool close to all

Home in Delavan
5 out of 5 average rating, 22 reviewsWinter Specials ~ Family friendly & dogs welcome

Home in Fitchburg
5 out of 5 average rating, 3 reviewsCountry Living/Downtown Access

Home in Lake Geneva
5 out of 5 average rating, 27 reviewsCozy cabin getaway near Lake Como and Lake Geneva

Home in Wisconsin Dells
4.89 out of 5 average rating, 63 reviewsWis. Dells River Haven Condo

Home in Poynette
4.8 out of 5 average rating, 46 reviewsYour Home Away From Home!

Home in Fontana-on-Geneva Lake
5 out of 5 average rating, 10 reviewsTreetop Lakehouse at Abbey Springs
Apartment rentals with a pool

Apartment in Wisconsin Dells
5 out of 5 average rating, 3 reviewsCondo in Wisc Dells for 10-14 ppl

Apartment in Wisconsin Dells
4.81 out of 5 average rating, 59 reviewsEntire Condo Sleeps 6 at Tamarack

Apartment in Fontana-on-Geneva Lake
4.78 out of 5 average rating, 179 reviewsFUN-tana All Year Round Abbey Springs Fontana WI

Apartment in Wisconsin Dells
4.82 out of 5 average rating, 226 reviews*Pool/Hot Tub | Riverwalk Retreat @ Dells Vacay | Cozy 2 BR Condo | Breathtaking Views | Downtown WI Dells

Apartment in Wisconsin Dells
4.9 out of 5 average rating, 20 reviewsGetaway+FREE Waterpark Passes

Apartment in Lake Geneva
4.96 out of 5 average rating, 23 reviewsElegant 4-Season Lake Geneva Condo w/ Fireplace!

Apartment in Lake Geneva
4.87 out of 5 average rating, 98 reviewsLake Geneva relaxation!

Apartment in Geneva
4.93 out of 5 average rating, 15 reviewsCozy 2 Bedroom Condo - Lake Geneva
Quick stats about holiday rentals with a pool in Madison
Total rentals
50 properties
Nightly prices starting at
$27 SGD before taxes and fees
Total number of reviews
760 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
- Milwaukee Holiday rentals
- Wisconsin Dells Holiday rentals
- Lake Geneva Holiday rentals
- Galena Holiday rentals
- Oshkosh Holiday rentals
- Rockford Holiday rentals
- Appleton Holiday rentals
- Schaumburg Holiday rentals
- Dubuque Holiday rentals
- Sheboygan Holiday rentals
- Lake Delton Holiday rentals
- Chicago Holiday rentals
- Rentals with pools United States
- Rentals with pools Wisconsin
- Waterfront rentals Madison
- Rentals with a washing machine and dryer Madison
- Flat rentals Madison
- Rentals with outdoor seating Madison
- Rentals with beach access Madison
- Rentals with lake access Madison
- Rentals with breakfast Madison
- Rentals with a fireplace Madison
- Serviced apartment rentals Madison
- Private suite rentals Madison
- Rentals with a firepit Madison
- House rentals Madison
- Fitness-friendly rentals Madison
- Rentals with a patio Madison
- Family-friendly rentals Madison
- Cabin rentals Madison
- Pet-friendly rentals Madison
- Cottage rentals Madison
- Apartment rentals Madison
- Monthly Rentals Madison
- Hotel rentals Madison
- Villa rentals Madison
- Rentals with a hot tub Madison
- Family-friendly rentals Madison
- Rentals with pools Milwaukee
- Rentals with pools Wisconsin Dells
- Rentals with pools Dane County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom