
Pet-friendly holiday rentals in Madison
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Top-rated pet-friendly home rentals in Madison
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Pet-friendly house rentals

Great location near the lake/bike loop!
One of the things I really appreciated was how proactive Mark was in his communications. He reached out before, during and at the end of our stay. We enjoyed the comfortable beds, the well-stocked kitchen and grilling out on the patio. We also appreciated having a queen in each bedroom. Mark gave us some good recommendations for nearby restaurants. The house was conveniently located and the neighborhood felt very safe. Would definitely recommend!

Island View Hideaway-Peaceful, On Water, Sandbars!
Beautiful spot to relax, close to great hiking trails. The home was comfy and had some thoughtful extras.

Fully Renovated 2BR 1BA Gorgeous Exec Home #8ma-R
Kevin was a great host! And the location was simply spectacular. Exceptionally clean house, included all and more of the amenities needed for our stay, and to top it all a great, peacefull and accesible neighboorhood. Made our Wisconsin stay amazing!

Coffee with a View
Couldn't have asked for more. Fantastic property and a responsive, friendly host. He even reached out to offer early check-in. We'll be back! From the wife: One of the best stays we’ve had! The host was super responsive—when our kids lost a ball, Kevin showed up with 2 new ones AND chalk. The cabin was spotless, with cozy couches, blackout curtains, comfy beds, & blankets everywhere. We loved the smart fridge for music, strong Wi-Fi, & the heated toilet seat (game changer!). Shower had great pressure, towels were plush & smelled amazing & the AC kept us cool. Porch felt like a villa in Costa Rica, especially in the rain. Early check-in, a generous welcome gift & even dog bags for our pups. Massage chair, grill, and space to spread out—we will DEFINITELY be back again, next time without our crazy children!

Lakeside Getaway
We had a great stay at Lexi’s place. The view is great and the house had everything we needed to make ourselves at home for the week. We would definitely stay here again when we are in the area.

The Tailor House: 2BR w/ Hot Tub near Woodstock Sq
Great stay! House has a ton of character, private hot tub was lovely! Well stocked and comfortable! Will definitely come again next time we’re looking to get away!

Fun Lake Kosh Private Pier, Decks, Fire Pit, Grill
Wonderful home for a big family or group! Lots to do (if you’re not already busy!). The home has everything you need to rest, relax, and make killer meals. Madison is a quick 30 minute drive away as well. Highly recommend.

Welcome to the Cambridge Lake House in Wisconsin!
Keith’s Airbnb was the perfect spot for a small family + dog getaway to a quiet lake in Wisconsin. We had a great host! The place was clean and spacious with every amenity that we needed. We cannot wait to return.
Pet-friendly home rentals with a pool

Family Fun! Hot Tub•Fire Pit•Game Room•3 Kings!
Another wonderful stay! This was our second year booking this amazing getaway home, and it was just as perfect as we remembered. Everything was clean, comfortable, and thoughtfully prepared. The location is unbeatable, and the hosts are always a pleasure to communicate with. We’re already looking forward to coming back next year!

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
Very accommodating and family friendly place. Our family enjoyed being outside every free minute we had.

Pools, Hot Tub, Fire tables, dog friendly
We had a wonderful stay! Doreen was always in communication making sure we had everything we needed. Our family of 5 was looking to getaway for a few days and this was a great place for it! The home was clean and cozy with lots of thoughtful touches throughout to make us feel welcome. We got to enjoy the amenities at the club house, and were just close enough to town to enjoy the restaurants and shops. My kids want to come back already!

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!

Aspen House - A Private Quiet Getaway In Nature
We had a really wonderful stay here over Memorial Day weekend. My two and four year old loved the toys and the movie screen (our daughter cried when we left). My husband and I thoroughly enjoyed the screened in porch. We’ve been to Galena now many times and this was our favorite place we’ve stayed at yet!

Farmhouse Chic|Fireplace|View|Peloton|Near Town
Such a wonderful Airbnb with a great location. Has everything you need! Definitely recommend!
Private, pet-friendly home rentals

Driftless Trout Cabin - Hillsboro, Wisconsin
Unbelievable how quiet it was at this location! The road it is on might have 1 car drive by per hour during the day, with much less cars at night. Great location in the countryside with Amish bakeries and businesses nearby. It is stocked with just about all the kitchen utensils and things you need for normal cooking, including some spices and seasonings, and the bathroom is supplied with all the necessary things, with a little more. The swing on the covered porch is excellent for relaxing, and night time sleeping, as is the couch. The firewood is cut perfectly to fit in the wood stove that very adequately heats up the place. The spring water that supplies the cabin will make your skin feel great after a warm morning shower. I was not a fan of the thought of having to wake up in the middle of the night and have to take care of nighttime bathroom needs by going up and down the ladder, so I never went up to the loft. I look forward to staying there again, hopefully during a snowstorm.

Peaceful Guest Suite at The Retreat
Liz was very responsive and very kind. She made the space feel cozy and relaxing. She was incredibly nice and checked in throughout our stay. The detail and thought put into the Airbnb made our time there memorable and relaxing, including extras for our dog staying with us. I would highly recommend this space for anyone coming to the area.

Prairie-Chic Downtown Lakeside
Alexander's flat in Madison was perfect for our stay. Right downtown, a stone's throw from the capital, and about a mile from the heart of the UW campus, this home was fantastic with a beautiful view of Lake Mendota. The best part of the experience was how easy it was to work with Alexander. He was very responsive to every question, he was proactive about giving us information needed for an easy and comfortable stay, and he was extremely thorough in the information needed about checking in and out of the apartment. All in, this was a great experience and I would absolutely stay here again. Thanks Alexander. - Joe S

Dottie's Place with a valley view
The beauty of the farm, the driftless area with steep hills and gorgeous valleys with a stream meandering through it was absolutely breathtaking! Different times of the day, different light and different beauty! Monet would have been in Heaven! We were there at the perfect time! Springtime! Lots of Red Winged Blackbirds weaving their nests. Barn swallows busily building their nests. And the best of all a fawn was born the day before we left!! Heaven! A truly magical place! And the house was so well appointed! A full kitchen, a beautiful fireplace, a huge master bedroom with en-suite bathroom, large windows framing the beautiful landscape, very comfortable and cozy. Much fancier than the photos depict! A perfect place for a retreat! Steve and April were Wonderful hosts who love sharing their property with guests and enjoying sharing about healthy farming, health and prairie restoration.

Secluded in the Woods, Hot Tub
My group had the best time at Owl's Rest! The cabin is surrounded by beautiful woods and relaxing peace. We sat at watched birds and all kinds of animals on the deck most of the day and sat by the fire at night. The hot tube was so perfect and relaxing. One night we walked down to the bar and had a fantastic meal and fun environment. Everything about this cabin was clean and well appointed. It was so hard to leave. You can't go wrong with this cabin if you're looking for a quiet, peaceful, and relaxing time. Lyle is very helpful and communicative. Literally the most perfect weekend in every respect. Thank you!

Cozy Lakeside Cabin on Lake Koshkonong
My husband, two dogs and I thoroughly enjoyed our stay at the cabin! The point of my vacation was going somewhere we could take our dogs and this was the perfect spot to relax with them for a few days. Everything was clean and there was a perfect amount of space for us to relax. It was very quiet in the neighborhood and most of the time it felt like we were the only ones around. It was great to be able to walk to a very nice restaurant and bar a minute or two down from the cabin since we wanted to stay close. The only thing that bummed me out was we went at the end of May and the dock wasn’t put out - and I was hoping to spend time sitting out on the water. That could have been me not realizing the typical “season” but had assumed it’d be out so I recommend checking if that’s important to you :)

Prime Time - 3 Bedroom with Fireplace! Sleeps 12
If you have a chance book it. It was lovely home away from home for our family. Tami was a fantastic host and the house is even more beautiful than the photos. Thanks so much!!!

Waterfront Condo 2Blocks to Capital GREAT Location
Chris’ place was worth every penny. The apartment was private and quiet while being so near to all the city has to offer. Killer restaurants and parks within short walking distance and the balcony overlooking the lake was the perfect place to have dinner. We parked the car and didnt feel the need to drive it anywhere once we got in - just walked the neighborhood.
Quick stats about holiday rentals that are pet-friendly in Madison
Total rentals
240 properties
Total number of reviews
16K reviews
Family-friendly rentals
120 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
160 properties have a dedicated workspace
Wi-Fi availability
240 properties include access to Wi-Fi
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- Wilderness Territory
- Kalahari Resorts Wisconsin Dells
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