Family-friendly vacation 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 pool

Guest favorite
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 favorite
A spacious backyard is presented with green grass and mature trees surrounding a playground. A wooden play structure features a slide and a swing set, providing ample space for outdoor activities. The area is well-maintained, offering a safe and inviting environment for children to play.
Apartment 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 favorite
A circular swimming pool is surrounded by a spacious patio with numerous lounge chairs. Lush greenery and trees frame the area, while nearby, a gazebo offers shaded seating. The multi-story condominium buildings in the background complete the inviting outdoor environment.
Condo 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.
Superhost
A covered patio area features a set of four cushioned chairs and a small decorative table. The view overlooks a calm stretch of water, with boat docks visible in the distance and gently sloping green grass leading down to the water's edge.
Condo in Wisconsin Dells
4.83 out of 5 average rating, 233 reviews

*Pool/Hot Tub | 2 BR Condo | Waterfront | Downtown

MirenasRating, 5 stars2 weeks ago
Very cute corner unit. My dad would just sit out on the patio, watching people put their boats in the water and take their boat out of the water. Beds were very comfortable place was nice and clean. I would stay here again.
A well-maintained swimming pool is surrounded by a spacious patio. Light blue lounge chairs are arranged around the pool, offering ample seating. A colorful umbrella is positioned nearby, providing shade. The area features lush greenery, contributing to a serene atmosphere.
Cabin in Wisconsin Dells
4.67 out of 5 average rating, 76 reviews

Duplex Cabin Vacation BC

JaredRating, 5 stars1 month ago
Nice, peaceful place to stay.
Superhost
A warm and inviting living area features wood paneling and exposed beams. A spacious sofa, adorned with patterned throws, faces a large flat-screen TV. Natural light filters through sliding glass doors that lead to an outdoor space. A rustic stone fireplace adds a cozy touch.
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
A light-filled living area features a stone fireplace as a central focal point. Leather seating surrounds a wooden coffee table, while artwork depicting Lake Geneva adorns the walls. Large windows provide views of the outdoor scenery, and a staircase leads to an upper level.
Home in Fontana
4.6 out of 5 average rating, 5 reviews

Abbey Spring Resort Home |North Shore Hideaway

MichelleRating, 5 stars11 months ago
We had a fantastic time here! The property has an incredible deck that extends into the surrounding forest. We had breakfast outside every morning! If you love wildlife, you'll love this place.
Top guest favorite
A serene outdoor area features a saltwater pool surrounded by lounge chairs and a stone patio. Lush green grass and flower beds enhance the setting, with sprawling fields visible in the background under a clear blue sky.
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!

Family-friendly home rentals with air conditioning

Guest favorite
A single-story house is set on a well-maintained lawn, featuring a wooden exterior with a front porch and red railing. A paved driveway leads up to the house, while trees and open space are visible in the background under a clear blue sky.
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.
Superhost
Two light-colored Adirondack chairs are positioned on a grassy area, offering a view of the lush surrounding landscape. Wildflowers and tall grasses are visible in the background, providing a natural setting. A cluster of trees stands nearby under a clear blue sky.
Apartment in Baraboo
4.87 out of 5 average rating, 276 reviews

Orchard Prairie B&B

DavidRating, 5 stars3 weeks ago
Wow the place is much bigger than the photos show!!!! We saw maybe two or three bugs over the three nights we were there — which is to be expected when the place is next to the woods. The area is absolutely gorgeous. And do check out the Ski-Hi Farm that they own up the hill!
Guest favorite
A neatly arranged bedroom features a spacious bed with soft linens and accent pillows. Natural light fills the room through two large windows. A small bedside table with a lamp stands next to the bed, and a vintage-style ladder is positioned at the foot of the bed.
Home in Marshall
4.96 out of 5 average rating, 92 reviews

1898 Farmhouse on 75 acres - MJ's Farm

KevinRating, 5 stars1 month ago
We rented this super-clean, charming farmhouse for a UW-Madison graduation weekend. The drive back and forth required some planning, but the manicured grounds and rolling-hill farmland location were peaceful and relaxing. The kitchen had everything we needed, the WiFi was solid, and there was plenty of hot water and towels for everyone. It was a great stay!
Top guest favorite
A cozy living area features a stone fireplace with a wooden mantel, complemented by a flat-screen television above. Soft curtains frame the windows, and warm light emanates from the fireplace, creating a relaxed ambiance. A patterned rug and comfortable seating enhance the space.
Home in Whitewater
4.95 out of 5 average rating, 152 reviews

The Modern Cozy Spacious Corner

ErinRating, 5 stars1 day ago
Do not hesitate to book Connie’s place! She was so kind and sweet and accommodating! I travel with my twin teenage daughters and my son for wheelchair basketball camp at UWW. The girls and I had a great time exploring the city and surrounding areas while my son was at camp. I really enjoyed the weight room at UWW and my girls loved Studio 84, Bakehouse for cupcakes, paletas at Michoacana, and a quick auto repair at Omega. We also really enjoyed Salem brewing, Whitewater’s beach and just all of the simple, small town charm! We loved the hot tub and game room and Connie’s place truly had everything we could possibly need. We felt so comfortable and at home and she was super quick to respond when we had questions. She completely went above and beyond to make us comfortable and accommodate our needs. As a host myself in Chicago, I would absolutely give her 5+ starts for the cleanest and most welcoming Airbnb we’ve stayed at thus far and we travel often! 🩷
Superhost
A serene view of a well-maintained lawn leads to a sparkling body of water, surrounded by trees. A patio table and chairs sit on the stone surface, with a subtle path of stepping stones leading towards the greenery. Bright natural light casts gentle shadows across the scene.
Home in Whitewater
4.7 out of 5 average rating, 10 reviews

Tranquil Wellness Retreat with Lake Views and Gym

GraciaRating, 5 stars1 month ago
We really enjoyed our stay and definitely would return. The home was clean and we felt right at home. Our dogs loved the yard and the view overlooking the lake was beautiful. The home was just as described, and check-in was easy. Nathan was responsive and communicated well throughout our stay. I would recommend staying at Nathan's, he is a great host, and we were grateful for our time there.
Guest favorite
A view of the Wisconsin River is captured from the porch, framed by lush greenery and vibrant flowers. The expansive lawn leads to trees along the riverbank, enhancing the serene atmosphere. The distant outline of a boathouse is visible, along with a recreational seating area.
Home in Poynette
4.82 out of 5 average rating, 82 reviews

Badger Dig's- 1 night stays available weekdays!

DonnaRating, 5 stars4 weeks ago
Beautiful location! Perfect for a couple or a small family. We loved the proximity to the water. Truly a beautiful home in a quiet and peaceful setting.
Superhost
A cozy cottage exterior is enhanced by festive decorations, including small evergreen trees in pots positioned along the pathway. The blue siding of the cottage is complemented by a welcoming entrance, with seasonal ornaments and a flag visible nearby, surrounded by a natural landscape.
Cabin in Edgerton
4.8 out of 5 average rating, 80 reviews

On Rock River/Lake Koshkonong Area

GabrielRating, 5 stars3 months ago
Came here for my spring break wanting to get out of the city and enjoyed my entire trip! The cabin was beautiful and the Rock River was majestic to gaze upon from the back porch. While I would have enjoyed more to do within walking distance, a drive as little as 30 minutes will get you to some wonderful places.
Top guest favorite
The historic limestone home features a welcoming red door and large windows, allowing ample natural light. A snow-covered path leads to the entrance, and a neatly stacked pile of firewood is visible beside the house. Surrounding trees are lightly dusted with snow.
Farm stay in Shirland
4.9 out of 5 average rating, 244 reviews

Historic limestone farmhouse, nature preserve.

JayRating, 5 stars3 months ago
Unique, comfortable, well-outfitted, historic home in a peaceful location. This was our 2nd time staying here and it was as lovely as we remembered. Large rambling farmhouse adjacent to restored wetland with miles of trails. Dave was a gracious host, communicative and responsive. This is a somewhat remote location and there are no stores or restaurants nearby but plenty of options within 15-30 minutes drive. Bring your own food and have a well-appointed kitchen in which to prepare it and a big dining room to share it. We appreciated several options for hiking nearby and that downtown Beloit was a short drive away. Highly recommended.

Family-friendly home rentals with a hot tub

Two wooden cabins are nestled among tall trees, showcasing a serene natural setting. One cabin features a welcoming porch with light illuminating the entrance, while the other cabin's windows are softly lit, hinting at the cozy interior. A lush green lawn complements the rustic ambiance.
Cabin in Wisconsin Dells
5 out of 5 average rating, 5 reviews

Cozy 2 bedroom with Fireplace

BritishRating, 5 stars39 months ago
I highly recommend this place for a small family or a small group. Riv’s Cottage is so cute and cozy. The staff was nice, everything you needed was on the Resort. I took my kids for Spring Break, we also went into town which is only 10mins away, waterparks, Arcades and good eats! If you want a home away from home check out Riv’s place, you won’t be disappointed.
Guest favorite
A spacious hotel room is shown, featuring a king-size bed with crisp white linens. A large flat-screen TV is mounted on the wall. A leather sofa and a small workspace with a chair are positioned nearby. Light enters through a window, highlighting warm wall colors.
Apartment in Wisconsin Dells
4.9 out of 5 average rating, 10 reviews

King Hotel Room @ Spring Brook Resort

AubreyRating, 5 stars1 week ago
Great little place free of the hustle and bustle of the Dells. Wonderful amenities and Very very clean!! Will definitely be coming back!
Top guest favorite
A spacious living area features modern furniture with a large sectional sofa and a coffee table. A mounted large smart TV is adjacent to a stylish modern fireplace, providing a warm ambiance. Light-colored walls and flooring create an airy feel throughout the space.
Condo in Wisconsin Dells
4.97 out of 5 average rating, 182 reviews

Stunning Condo, Beachfront, Fireplace, Jacuzzi

KellyRating, 5 stars4 days ago
Pretty and peaceful lake complex. This condo is in a great location within the well maintained complex. Jody and Jana are great hosts, the condo was well stocked and had all the little extras that made it very comfortable for our family.
Top guest favorite
The resort entrance is framed by lush greenery and decorative flower beds. A rock waterfall feature adds a natural touch, while the spacious driveway leads to a charming building with a sloped roof and wooden accents.
Cottage in Wisconsin Dells
4.84 out of 5 average rating, 51 reviews

Enjoy Fun & Relaxation This Summer in Wis. Dells!

AndreyRating, 5 stars1 day ago
We enjoyed our stay! The cottage was spotless and had everything we needed for a family of 4 on a 4 day stay. The complex has many great amenities with multiple pools to the delight of our kiddos. It's a short drive to the Dells, where we went to eat, visited a waterpark and did a duck ride.
Guest favorite
Cabin in Wisconsin Dells
4.76 out of 5 average rating, 82 reviews

Cottage in a fantastic resort

TarynRating, 5 stars4 months ago
We have stayed multiple times at William’s Wisconsin cottage at Christmas Mountain Village. It’s always super simple and a great place to stay for families. William responds quickly to all questions and is a great host!
Guest favorite
The family room features a comfortable sofa with decorative pillows facing a large 58" Roku TV mounted on a wooden accent wall. An electric fireplace adds warmth, while a coffee table occupies the center space. Large windows allow natural light and open to a door leading outside.
Condo in Wisconsin Dells
4.87 out of 5 average rating, 295 reviews

The Docksider for Couples & Young Families

LucyRating, 5 stars1 week ago
This was our first vacation as a family with a 5 and 3 year old. Our neighbors were lovely. The beach was a great addition. The place was pristine and exactly enough for us. Perfect location close to everything and the communication leading up to the vacation was top notch. We had chilly weather but the vacation was just what we needed. Amazing view and super relaxing (even with the kids!) will definitely come back!
A spacious studio condo features two queen-size beds with warm, textured bedding. A wooden dining table with metal chairs sits in the foreground, while a small kitchenette with modern appliances is visible in the background. The warm-toned walls are complemented by framed artwork.
Condo in Wisconsin Dells
4.63 out of 5 average rating, 8 reviews

Romantic 2 Queen Studio Condo w/Jacuzzi+Fireplace!

JeanRating, 5 stars9 months ago
It was great! It was a beautiful place. Will definitely go back.
A person stands on a paddleboard, gliding across calm waters reflecting vibrant sunset hues. The sky is painted with soft clouds in shades of orange, pink, and blue, creating a serene backdrop for the tranquil scene.
Guest suite in Waunakee
4.82 out of 5 average rating, 303 reviews

Private guest suite on beautiful Lake Mendota

JacobRating, 5 stars1 month ago
Loved bug the car that greeted us every time we came in and out of the place! We were there when the May flies were hatching so we did not get to enjoy some of the luxury’s of the place but we are excited to come back soon!

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

  • Total rentals

    330 properties

  • Nightly prices starting at

    G$4,184 GYD 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