
Holiday rentals with a pool in Madison
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Top-rated rentals with a pool in Madison
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Popular amenities for Madison rentals with a pool
House rentals with a pool

Peaceful, Cozy Home w/ Club Amenities in Galena.
We had a wonderful stay! The house was stocked with everything we needed. The kids had so much fun with all the toys and games and us adults loved the deck and firepit. It was the perfect place for our family. We saw a bunch of wild turkeys, a few deer and lots of other wild life. Everything was clean, the beds were comfortable and the thoughtful extras were much appreciated. Brittany and Tim were great hosts!

Cozy Galena Townhome
The condo was immaculate and comfortable. Check in was easy and the host provided helpful information about finding the local store as well as a route suggestion to avoid exiting the neighborhood on a blind curve. Would definitely stay here again.

Perfect Location! Owner Club Access, Dog Friendly!
Our family—including me, my wife, our daughter, and our puppy—had a wonderful time. Ginger was very kind and provided detailed information, including how to use the amenities like the swimming pools. The property was clean, cozy, and conveniently located near downtown, where we had a great time exploring. We’d definitely recommend this place to any family and would love to return on our next trip to Galena.

Galena Getaway
Great location. So close to everything. Would definitely stay again!

Fox Wood Path l HOT TUB l A&D Rise Getaways
It was our first time to Galena. We were looking for a relaxing weekend getaway to celebrate our 20th. The house was exactly as described in a serene setting within Galena Territory. We enjoyed hiking, biking, and wineries all within a short drive, and then relaxing in the hot tub in the evenings. We didn't partake in any of the included amenities within Galena Territory, but noted it as a positive that we would take advantage of for future trips. We very much enjoyed our stay and hope to return soon!

Spacious Pine Cabin at Island Pointe
Lovely updated cabin among other cabins in resort on Lake Delton. Spent 3 days with my 2 sisters and enjoyed the peaceful surroundings as great getaway from, yet easy to reach Dells attractions. As summer fully starts next week I expect the place will be much busier as it seems a very good family resort with pool and playground for kids. Nice, sandy beach on lake a short walk away. There are stairs to access the cabin from the deck. Use key pad hidden behind upper deck screen/storm door. Lower level has nice extra family room to spread out guests. Bring Duraflame type logs if you’d like to use fireplace. We enjoyed that on a cooler night.

Awesome Lodge in Galena Territory
We had a great stay at the cabin for my brother’s bachelor party weekend. We played 2 golf courses, ate at one of the resort restaurants, and went downtown for dinner one night. It’s a 2 minute drive to the courses and 10 minutes to downtown. Great location that sat on one of the par 4s.

Paradiso Vacation
Everything looked exactly like the pictures. So much to do at the house that we wished we would have stayed an extra day or two. Lots of space for our group of 7.
Apartment rentals with a pool

Glass Vista: Modern 2BR Condo, Stunning Views
Great peaceful location, very clean and great host! Highly recommend this property!

Entire Condo Sleeps 6 at Tamarack
Kevin is a great host, we will definitely come back.

Chic Condo in Lake Geneva.
perfect is the word! we very much enjoyed Chad and Morgan's place. everything as described or better. good location and all the amenities we needed. comfortable bed, nice towels, nice view, overall we were super pleased. definitely worth the stay.

Your Boho Retreat
We had so much fun at our stay!! The place is extremely clean and has a brand new kitchen & new appliances. It's nice having a full bathroom downstairs & upstairs. The upstairs bedroom is lofted so the kids enjoyed seeing if various items of theirs could fly :)) There was a Roku box on both tvs upstairs and downstairs so it was easy to watch shows/movies. Wifi was solid. Its an easy walk to the activity center. They have tennis courts, pickleball, basketball, racquetball, pool & hot tub along with changing facilities; all free to reserve/use. You could probably spend all week here and never leave! It was our first time here so we did all the touristy things and loved it: Bellos Circus, Rick Wilcox Magic Theater, WizardQuest, Ripleys, Mirror Maze, Big Chief Gokarts, Kalahari Waterpark, Frischs BigBoy etc! It was super convenient having a walmart, DD, kohls, McDs, Ross etc so close. The house was very quiet. Be sure to bring shampoo and any food condiments, otherwise everything is here.

*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.

2BR Serene Riverfront • Spacious • Pool & Hot Tub
Great host and a great space. Reminded me of the early days of Airbnb when people went out of their way to make you feel welcomed and have a good time. Highly recommend!

Modern Lake Geneva Retreat
The condo surpassed my expectations. It was peaceful and the furniture was amazingly comfortable. I particularly enjoyed the L-shaped couch and over-stuffed chair. The master bedroom was large and had plenty of storage space. My kids took advantage of the TV being in the bedroom. The other bedroom was smaller, but very comfortable. I liked the additional pillows in the closet since some were more firm than others. The bathrooms were a bit outdated but not a big deal. The kitchen had everything as described. It was narrow, but it had all the space we needed. There was a washer and dryer which was an added bonus. The condo surroundings were perfect for us since there was so much green grass, rolling hills and trees. My kids wrapped themselves in blankets and rolled down the larger hill! The pool was in walking distance, and Nick had left pool noodles for guests which was a nice touch. As a host, Nick was great! Very responsive and friendly. ⭐️⭐️⭐️⭐️⭐️

Beautiful Condo at Chula Vista!
Great, comfortable place to stay for my birthday.
Quick stats about holiday rentals with a pool in Madison
Total rentals
50 properties
Nightly prices starting at
₹1,731 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
- Kalahari Resorts Wisconsin Dells
- Devil's Lake State Park
- Wild Rock Golf Club
- Noah's Ark Waterpark
- Mt. Olympus Water & Theme Parks
- Mt. Olympus Parks, Outdoor Theme Park
- Chula Vista Resort Water Parks
- Mirror Lake State Park
- Lake Kegonsa State Park
- Yellowstone Lake State Park
- Cabin 857-1- Christmas Mountain Village
- Devil's Head Resort
- Tyrol Basin
- Henry Vilas Zoo
- Tom Foolerys Adventure Park
- Wisconsin State Capitol
- Kalahari Indoor Water Park
- Lost World Water Park
- Mt. Olympus Parks, Parthenon Indoor Theme Park
- Cascade Mountain
- Klondike Kavern Water Park
- Alligator Alley
- University Ridge Golf Course