
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
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Popular amenities for Madison rentals with a pool
House rentals with a pool

Bennett Chalet @ Spring Brook Resort
The house is exactly as described. We had a group of 12 in town for a golf weekend and really enjoyed the location, layout, and massive table. Highly recommend!

Awesome Lodge in Galena Territory
Beautiful home, with awesome view of golf course. Plenty of space to move about , large deck to sit and relax. Alex was very accommodating on check in time and was very responsive. Gave us detailed instructions for checking in and checking out. Lighting was labeled so there was no guessing on which switches controlled which lighting which was very helpful

CountryView 3-BR cozy & stylish home w/hot tub
Beautiful and peaceful home surrounded by nature. We were looking to “unplug” and spend quality time together. We loved the pond, birdwatching and the hot tub on cold nights. The house is perfect and has everything you need. Downtown Galena is only a short ride away and we enjoyed learning about its rich history. Thank you for letting us into your cozy home.

Modern spacious 4 bedroom retreat with 3 en-suites
Oh boy a must stay we walked in and absolutely Beautiful!!! All our needs were met!!! Jacuzzi was so nice with fun lights!! Just so pretty!!! Would stay again loved it!!♥️

Luxurious BBQ and Pool House
Amazing place and such a nice area. The back yard was beautiful and close to all the perks of Madison.

*Golf*Hot Tub*Dogs Ok*Firepit*Owners Club*
Last minute my family and I decided we needed a getaway. Cynthia almost instantly approved our booking, gave instruction, and even photos and drawn details on how to get to the home. We were at the home within 4 hours of booking. She also gave us early check in without requesting. On the final night of our reservation we enjoyed this property and stay so much we asked about staying another night. Luckily it was available and approved again almost instantly. The home was very clean, provided extras like toothbrushes, hair appliances, shampoo, keurig & popcorn. Our kids loved the loft area, games, and the space to explore outdoors. The layout was open and cozy. It was just far enough away for peaceful privacy but still close enough to get into town in 15 minutes. We didn’t want to leave!

Galena Retreat - Eagle Ridge Territories
Really enjoyed our stay! Clean and comfortable and felt right at home. Thanks Sandy!

N 2nd St Pool House
We stayed here for just the weekend but even with our short stay it was a great experience. Beautiful house, feels cozy and the indoor pool is such a plus! We all had a great time here, definitely keeping this in mind for any future bookings or getaways.
Condo rentals with a pool

Condo in Wisc Dells for 10-14 ppl
We had a wonderful family stay (for a wedding at CVR). The place was super clean, well-appointed and lots of little extras. Our only negative was no grill (there is a community one, but too far away for it to be convenient), but we went into it knowing that, so all good. Would highly recommend staying here. Beautiful setting, water park across the parking lot. Julie was very accommodating. Great set-up for having small children with us - and we had 3 bathrooms, a bonus. Would definitely recommend this place for a stay in the Wisconsin Dells!

Serene Riverfront 1BR • Jacuzzi • Pool & Hot Tub
I absolutely loved this place. It was quiet and cozy. I will definitely book again when I’m in the Dells.

COZY, Lakefront, Fireplace, Free Kayaks
Jody & Jana were responsive, helpful, and inviting. Their condo is in a beautiful location.

FUN-tana All Year Round Abbey Springs Fontana WI
Joan's daughter, Rebekah, communicated directly with me through the Airbnb app. She provided detailed check-in instructions, a phone number to contact her, etc. It seems Rebekah lives in Hawaii so please keep note of that for response times, etc. The house was comfortable, very clean, and well-appointed. Joan and Rebekah have a beautiful collection of original art, artifacts, etc. so please keep that in mind if you are bringing small children to the home. Please note that the 1st floor bedroom has a king bed and full bathroom; and the lower level has 2 twin beds in the open area, 1 full bed and 1 twin bed in the first bedroom, and 1 full bed and 1 futon in the second bedroom (including a full laundry and utility room in a closed room).

*Pool/Hot Tub | 2 BR Condo | Waterfront | Downtown
Really nice apartment in a beautiful location right on the river. So peaceful in the morning. Very easy to find and get into. Exactly as described. Coffee pot with coffee bags, sugar and creamer including microwave popcorn and chocolate biscuits. Nice welcome pack. Lots of cutlery crockery and pans but didn’t see any oil or condiments. If you are going to cook you’d need to bring some. Had problems with the tv instructions but after contacting Ashley somebody came to the condo within 15 mins and sorted out for us. May need to update instructions or check settings haven’t been touched to save inconvenience. Just to note the smaller bedroom has the boiler in it which is very noisy. We had ear plugs so was ok for us but if you come in the cold weather and need heating you would need to bear in mind. Overall a lovely stay in a quiet area of town within a short walk to all amenities. Would recommend.

Dells Getaway At Tamarack Resort with Boat Slip
The perfect trip for our family. The place was spacious for our family of four. Perfect location conveniently located to the Dells/Delton, but quiet and removed enough to be peaceful. The activity center, arcade, and playground was a nice addition and able to enjoy our times on the grounds. Great price as well. Looking forward to the next trip.

Magnificent waterfront views & cozy fireplace
"5-star stay! Clean, convenient, and great value. Would book again!"

LakeView-SummerPool-FamilyFriendly-CloseToTown
We loved our stay at this beautiful location. It was close by to everything we wanted to do and the condo was exactly what we were hoping for! Rachel gave great recommendations and was so responsive to our questions. We will definitely stay here again!
Quick stats about vacation rentals with a pool in Madison
Total rentals
50 properties
Nightly prices starting at
ﺩ.ﺇ73 before taxes and fees
Total number of reviews
540 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
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- Wilderness Territory
- Chula Vista Resort Water Parks
- Wild Rock Golf Club
- Kalahari Resorts Wisconsin Dells
- Devil's Lake State Park
- Noah's Ark Waterpark
- Devil's Head Resort
- Lake Kegonsa State Park
- Mirror Lake State Park
- Mt. Olympus Parks, Outdoor Theme Park
- Henry Vilas Zoo
- Mt. Olympus Parks, Parthenon Indoor Theme Park
- Yellowstone Lake State Park
- Cabin 857-1- Christmas Mountain Village
- Lost World Water Park
- Mt. Olympus Water & Theme Parks
- Cascade Mountain
- Tom Foolerys Adventure Park
- Wisconsin State Capitol
- Extreme World
- Alligator Alley
- Klondike Kavern Water Park
- University Ridge Golf Course
- Tyrol Basin