
Holiday rentals with a pool in Madison
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Top-rated rentals with a pool in Madison
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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!

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.

Cozy Retreat | Hot Tub | Firepit | Dog-friendly
Brian and Jonny were very responsive and communicative from beginning to end. It was a last minute trip and we were lucky to find a pet friendly place during the start of the summer season. The house was clean, cozy and close to walking trails. Although we did not take advantage of the outdoor grill or hot tub (they have a wood burning fireplace for the winter), we enjoyed the screened in porch and open concept layout of the house, as pictured in the profile. The house is situated between two other houses blocked somewhat by the trees. I would describe as semi-private where we could see their back patio/hot tub/fire pit and vice versa. But whatever your personal comfort level, you can’t beat the proximity to trails, Owners Club, and easy access to Hwy 20 to Galena! We enjoyed our stay and exploring!

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

Treehouse Retreat | Hot Tub • Firepit • Games
We had the absolute best time at The Treehouse. It was truly one of the most spectacular places we’ve ever stayed! From the moment we arrived, it felt like the perfect home for a family getaway. The house had everything we could have possibly needed for comfort, fun, and quality time together. It was sparkling clean, beautifully maintained, and the views were just breathtaking. Our hosts were wonderful. They were so kind, responsive, and helpful throughout our stay. We especially loved relaxing by the fire pit, unwinding in the hot tub, and enjoying the peaceful screened-in porch. It was the perfect balance of cozy and fun! Beyond the amazing home itself, Galena had so much to offer. We had a great time exploring the town, dining at local restaurants, shopping, and just soaking in the charm of the area. We’re so grateful for our stay at The Treehouse and can’t recommend it highly enough. We’re already hoping to return for another family gathering next year!

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.

Family-Friendly Wooded Retreat- 3 Ensuite Bedrooms
Joel’s place was absolutely beautiful! It was secluded and peaceful but also very close to down town. I loved drinking my coffee outside in the mornings it was so peaceful! I’d recommend Joel’s air bnb to anyone wanting to travel to galena. I’d go back in a heartbeat! Joel was a great host. He gave us all the information and checked In on us throughout our stay. We had a great time!
Apartment rentals with a pool

Lakefront Condo - Private Beach | Boat Slip| Pool
Amazing place .highly recommend!!

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
Excelente lugar para descansar y estar en familia, muy limpio y organizado

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.

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
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- Lake Kegonsa State Park
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- Wisconsin State Capitol
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