Family-friendly holiday rentals in Madison

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Madison family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favourite
Home in Galena
4.96 out of 5 average rating, 282 reviews

Comfortable 4 Bed 4 Bath in the Galena Territory!

DianeRating, 5 stars1 week ago
Stayed here for a sisters weekend- and it was great for 6 sisters between the ages of 60-75. Two bedrooms on main floor and 2 downstairs worked great for us. Things were a little dated- but hey- so are we. We had a couple of issues that needed attn and James was most attentive and took care of them immediately. I would recommend. Great value for 6 women with varying needs! Especially loved the hot tub in the natural surroundings!!!
Superhost
Flat in Galena
4.88 out of 5 average rating, 8 reviews

Galena 1 Bdrm Condo Resort

NnekaRating, 5 stars66 months ago
This place was amazing! Fireplace. Bigger than expected. Very clean. The hospitality was dope! Great view of the "mountains" . Pretty cool experience. The extra pull out bed is such a nice touch!
Top guest favourite
Home in Galena
4.92 out of 5 average rating, 160 reviews

DunPuttin Place

EmilyRating, 5 stars2 weeks ago
Stayed here for a girl’s trip! The home is lovely. The game room downstairs was a blast. The deck in back was perfect for drinks and conversation at night and calm morning coffee in the morning! Todd is quick to respond if anything is needed. Would definitely go back
Superhost
Apartment in Galena
4.93 out of 5 average rating, 28 reviews

Galena, IL, 1 Bedroom S #1

HollyRating, 5 stars33 months ago
Jan’s condo is a perfect location for galena. It’s not far from downtown or Eagle Ridge. It’s like the comfort of home without being home.
Superhost
Home in Galena
4.75 out of 5 average rating, 28 reviews

Amazing 6BR! Whiskey Room, pool table & hot tub-su

ThomasRating, 5 stars3 weeks ago
This was a great spot. The surrounding area is really beautiful, especially when I visited (in the late spring), and lots of the house layout helps you appreciate this, whether it’s inside or out. The home is spacious, the fire pit was lovely at night (and well stocked), and the host was plenty responsive. Would stay again.
Guest favourite
Holiday home in Galena
4.91 out of 5 average rating, 253 reviews

5BR Country Stay | Pond, Jacuzzi & Views

AaronRating, 5 stars1 week ago
Lovely home and property, lots for the kids to do outside, easy to get to, very private. Three families with young children stayed here comfortably. Easy access to Galena but honestly we could have just stayed at the house all weekend. The play equipment and treehouse were safe and sturdy. Would definitely stay here again!
Guest favourite
Home in Richmond
4.93 out of 5 average rating, 156 reviews

"About Time" You will love it! -12 beds

SteveRating, 5 stars5 months ago
Very nice place to host our large family Christmas gathering. Plenty of room for everybody. The game room was very much appreciated and well used.
Superhost
Flat in Wisconsin Dells
4.67 out of 5 average rating, 9 reviews

King Hotel Room @ Spring Brook Resort

BlakeRating, 5 stars3 weeks ago
our new favorite spot to stay in the Dells!

Family- and pet-friendly home rentals

Guest favourite
Home in Baraboo
4.89 out of 5 average rating, 109 reviews

Wild Rose Ranch Guest house

ChristyRating, 5 stars5 months ago
The house was very spacious for our family of 6. We loved the location, view, and short drive to everything we wanted to do.
Guest favourite
Townhouse in Blanchardville
4.93 out of 5 average rating, 174 reviews

Dottie's Place with a valley view

TracyRating, 5 stars3 weeks ago
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.
Top guest favourite
Guest house in Stockton
4.98 out of 5 average rating, 363 reviews

Highview Country Escape - Cozy Cabin with a view

RafalRating, 5 stars1 month ago
We had a fantastic stay at this beautiful property nestled on a hill in the middle of nature. The location is peaceful and scenic—perfect for a relaxing getaway. Our dogs absolutely loved the wide open space to run and explore, which made the trip even more special. One of the highlights was the lovely pond on the property, full of fish and a great spot to sit by and enjoy the surroundings. Highly recommend this place for nature lovers and pet owners alike!
Superhost
Home in Poynette
4.85 out of 5 average rating, 268 reviews

Quietwater-Peaceful, On Water, Nature, Sandbars!

BarbaraRating, 5 stars3 weeks ago
We very much enjoyed our stay. The location and view were lovely and quiet. We especially enjoyed the wildlife from the deck and the hot tub! We even had a bald eagle visit for a couple of hours on the sandbar right in front of us. The cottage was very clean and comfortable. A very relaxing weekend!!
Guest favourite
Guest house in Spring Green
4.95 out of 5 average rating, 116 reviews

Teacher’s Lounge

KimRating, 5 stars1 week ago
LOVED this place!! The garden outside is spectacular. Daisy the dog is a sweet greeter, and Aaron was super friendly and helpful. We love the Spring Green area, and this location could not be more perfect. The space is spotless, comfy, quiet, and looks exactly like the pictures. We will be back the next time we come to see a show at APT!! Thank you for your kind hospitality.
Guest favourite
Home in Edgerton
4.92 out of 5 average rating, 121 reviews

Fun Lake Kosh Private Pier, Decks, Fire Pit, Grill

JoeyRating, 5 stars1 month ago
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.
Guest favourite
Flat in Albany
4.94 out of 5 average rating, 188 reviews

Sugar River Hideaway

AngelaRating, 5 stars1 week ago
The place ended up better then we expected, the pictures don’t quite so it justice. It was extremely clean and comfortable. Despite being on a street surrounded by businesses and bars it was nice and quiet. It was about a 20 minute drive to New Glarus.
Superhost
Chalet in Williams Bay
4.88 out of 5 average rating, 253 reviews

The Bay Chalet

KaitlinRating, 5 stars1 week ago
The place had everything we needed and had two outdoor spaces to enjoy which we value in an Airbnb. A touch less private than I expected, I’d say, and lawn work noise throughout the Saturday we were there (no fault of the host!). But it was definitely clean, comfy, had a well-equipped kitchen with a blender/full-sized coffee maker/good knives, and was a great deal. Holly was also very kind to extend our reservation a day due to a family emergency.

Family-friendly home rentals with a pool

Guest favourite
Home in Apple River
4.93 out of 5 average rating, 81 reviews

The Ho Hum East on Apple Canyon Lake

KathyRating, 5 stars1 week ago
This was our second time at Ho Hum East and we had a great time! The new deck updates were super nice adding outdoor space to layout food and enjoy most meals on the deck. The outdoor kitchen wasn't completed yet but, will be a great addition to the new deck when it's done. The main bath was newly remodeled and was very nice and spacious. The lake front was well maintained and a great space for us to spend most of our time enjoying the water, sun, fishing, boating, nature and wildlife. The dock was a little wobbly although, we were told that was being replaced at some point but it worked for us. The airbnb owner provided a paddleboard, rubber raft, corn hole boards and other outdoor items to use. The proximity of the home was only a few minutes from amenities i.e. pool, golf course, beach and The Cove (restaurant). The only drawback is all the steps - it would be great if there was a pulley system or other system to take items up and down the steps from the house to the lake front.
Guest favourite
Flat in Madison
4.85 out of 5 average rating, 13 reviews

Professionally Serviced Private 1BR Apartment

CatherineRating, 5 stars4 months ago
great place to stay, central to the madison area, clean, and great community.
Guest favourite
Apartment in Fontana-on-Geneva Lake
5 out of 5 average rating, 58 reviews

2 BD 2 BA Abbey Villa with Pool

GavinRating, 5 stars10 months ago
Great spot! The condo was clean, comfortable, and quiet. It was a short walk to the beach and restaurants. Mandy’s detailed directions and instructions made checking in a breeze. Our group of four had a fantastic time.
Guest favourite
Home in Wisconsin Dells
4.88 out of 5 average rating, 217 reviews

Spacious Pine Cabin at Island Pointe

MarjorieRating, 5 stars1 week ago
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.
Superhost
Villa in Lake Geneva
4.9 out of 5 average rating, 77 reviews

2 Bedroom Villa at Lake Geneva's GRAND Resort

LoriRating, 5 stars3 weeks ago
What a lovely and hospitable place! We loved our time there. The level of comfort was unmatched. We would happily return. Truly a wonderful experience!
Top guest favourite
Guest suite in Mount Horeb
4.99 out of 5 average rating, 75 reviews

Rural Luxury w/pool in the heart of Wisconsin!

StaceyRating, 5 stars10 months ago
Beautiful house and view. Would definitely stay again!
Guest favourite
Home in Galena
4.82 out of 5 average rating, 295 reviews

Galena Retreat - Eagle Ridge Territories

RayRating, 5 stars2 weeks ago
Even better than advertised. Sandy was wonderful and so was the home. We were very pleased with our stay and her communication. The house is in a nice, quiet neighborhood, close to the strip, around golf courses, wineries, great food, fishing, historical places, and kayaking. Thanks again Sandy, we will be talking to you soon I’m sure.
Superhost
Home in Galena
4.83 out of 5 average rating, 65 reviews

Beautiful home with wooded surrounding, WIFI

RachaelRating, 5 stars8 months ago
We had a fantastic stay for our “Mom’s-Away” weekend. One thing to note- google maps brought us down a different street where there is no access to the house. Unsure why that was the default direction, but you just need to ensure you take the designated street to get to the house. It was especially confusing as there must be another rental since there were signs that said “XYZ Home This Way” haha. The screened porch was so relaxing we spent the majority of our time there.

Quick stats about holiday rentals that are family-friendly in Madison

  • Total rentals

    330 properties

  • Nightly prices starting at

    ₹1,731 before taxes and fees

  • Total number of reviews

    17K reviews

  • Pet-friendly rentals

    120 properties allow pets

  • Rentals with a pool

    20 properties have a pool

  • Rentals with dedicated workspaces

    190 properties have a dedicated workspace

Destinations to explore