Holiday Rentals in Madison, WI

637 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Madison, WI holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

637 Holiday rentals and Airbnb in Madison, WI

Best family friendly Madison, WI holiday rentals

Among the 637 accommodations in Madison, WI, here are the 4 best family friendly rentals

Updated 3 Bed + Office Ranch Home Close To Downtown Madison - Madison, WI
10 23 reviews

Updated 3 Bed + Office Ranch Home Close To Downtown Madison

apartment, Monona
This apartment in Monona is conveniently located just a short distance from downtown Madison, offering easy access to the city's attractions and amenities. It is also close to Lake Monona, providing access to the lake's walking paths, parks, and water activities. The apartment has received excellent user ratings, making it a popular choice for travellers.
This spacious four-bedroom home, spanning 149 square metres, can comfortably accommodate up to eight guests. Enjoy a modern and spacious living experience with a fully remodeled kitchen and bathroom, as well as a spacious screened porch, a basement with a bedroom/office and recreation room, and amenities including a gas grill, off-street parking, laundry facilities, high-speed internet, and cable TV.
Capital City- 6 Miles From Madison With Fireplace - Madison, WI
10 54 reviews

Capital City- 6 Miles From Madison With Fireplace

apartment, Sun Prairie
This apartment is located in Sun Prairie, a quiet suburb just 6km from the state capital, Madison, and within easy reach of major amenities. It has received excellent user ratings and is perfect for families and groups.
The apartment has four bedrooms and three bathrooms, comfortably accommodating up to 12 guests. It offers a range of amenities, including a fully equipped kitchen, a terrace, a garden, and parking, as well as Wi-Fi and air conditioning.
Family Friendly House - Downtown Location! - Madison, WI
9.9 50 reviews

Family Friendly House - Downtown Location!

apartment, Madison
This apartment is located in a downtown Madison neighbourhood, just a short walk from Lake Mendota and Tenney Park, and less than 10 minutes by car or bike from the Capitol building, Monona Terrace, and the UW campus. The property has received excellent ratings for location, cleanliness, and overall user experience.
This five-bedroom dwelling can comfortably accommodate up to nine guests and features a spacious attic playroom with a queen-sized bed for additional sleeping space. Guests can enjoy modern amenities such as central air conditioning, fast internet, a hot tub, a garden, and canoes/kayaks/bikes available upon request.
Madison Lakefront Oasis In The Heart Of Madison - Central, Minutes To Downtown! - Madison, WI
9.8 56 reviews

Madison Lakefront Oasis In The Heart Of Madison - Central, Minutes To Downtown!

apartment, Monona
This apartment is located in Monona, a neighbourhood in Madison, within 5-10 kilometres of downtown Madison, the University of Wisconsin campus, and the Alliant Energy Center. It has received excellent user ratings.
The three-bedroom apartment is 111 square metres and can accommodate up to eight guests. It features a fully equipped kitchen, a terrace/balcony, a garden, parking, and a private dock on the Yahara River, giving you access to both Lake Monona and Lake Waubesa.

Best Madison, WI holiday rentals with parking

Awesome Location In Monona, With Hot Tub! - Madison, WI
9.9 33 reviews

Awesome Location In Monona, With Hot Tub!

apartment, Monona
This apartment is located in Monona, a short walk from three playgrounds, a library, and a community pool. It has received excellent ratings for location, cleanliness, and user experience.
The apartment has three bedrooms, three bathrooms, and can comfortably accommodate up to seven guests. It offers a range of amenities, including a fully equipped kitchen, a Jacuzzi, a garden, and a basement recreation room, making it ideal for families or groups looking for a relaxing and enjoyable stay.
Madison & ~Uw~-madison Area Lakefront Home - Madison, WI
10 213 reviews

Madison & ~Uw~-madison Area Lakefront Home

cottage, McFarland
This McFarland cottage is located just 3 kilometres from Lake Waubesa, the Aldo Leopold Nature Center, and the Capital Springs State Recreation Area, offering easy access to outdoor activities and natural beauty. It has received excellent user ratings, making it a popular choice for travellers.
The cottage spans 130 square metres and comfortably sleeps six guests in its three bedrooms and two bathrooms. Guests can enjoy a range of amenities including a fully equipped kitchen, a patio, a swimming pool, and a spa, ensuring a relaxing and enjoyable stay.
Newly Renovated 2 Bed 1 Bath Apt, Close To All - Madison, WI
9.6 275 reviews

Newly Renovated 2 Bed 1 Bath Apt, Close To All

apartment, Fitchburg
This charming flat is situated in Fitchburg, within easy reach of local amenities and services. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The apartment offers a comfortable and spacious layout that can comfortably accommodate up to four guests. It comes equipped with all the essentials for a pleasant stay, including a fully equipped kitchen, air conditioning, off-street parking, and laundry facilities.
Cheerful 3-bedroom Cottage 2 Blocks From The Lake - Madison, WI
9.8 101 reviews

Cheerful 3-bedroom Cottage 2 Blocks From The Lake

apartment, Monona
This charming cottage is situated in Monona, just a short walk from the lake and a 12-minute drive from downtown Madison. The property consistently receives excellent ratings from guests for its cleanliness, location, and overall experience.
This cosy holiday home offers three bedrooms, comfortably accommodating up to six guests. The cottage includes a fully equipped kitchen, air conditioning, a spacious garden, and parking, making it ideal for families and groups seeking a relaxing and comfortable stay.

Frequently asked questions about holiday rentals in Madison, WI

  • What should a first-time visitor not miss in Madison, WI?

    You've got to visit the Wisconsin State Capitol Building. It's a beautiful piece of architecture and a must-see for any visitor. Another must-do is to take a stroll along the lakeshore path, especially around the University of Wisconsin campus. You'll get a great view of the city and the lake.
  • What are the best Airbnb and holiday rentals in Madison, WI?

  • Which neighborhood in Madison, WI should you consider for a vacation rental?

    If you're looking for a vibrant and lively area, consider staying in the downtown area, close to the Capitol Square. For a more relaxed vibe, you could check out the waterfront neighbourhoods of Lake Mendota or Lake Monona.
  • What are the most popular Airbnbs in Madison, WI?

  • What are the top family-friendly attractions in Madison, WI?

    The Henry Vilas Zoo is a great place to spend a day with the family. It's home to a wide variety of animals and has plenty of space to run around. Another option is the Wisconsin Historical Museum. It's got interactive exhibits that are sure to keep the kids entertained.
  • What are the best holiday rentals with a pool in Madison, WI?

  • When is the best time to book a vacation rental in Madison, WI?

    The best time to book a vacation rental in Madison is during the shoulder seasons, from April to May or September to October. You'll avoid the crowds and get better deals on accommodation.
  • What are the best rentals for families and kids in Madison, WI?

  • What events or festivals should visitors check out in and around Madison, WI?

    The city comes alive with festivals throughout the year. The Madison Jazz Festival in June and the Wisconsin State Fair in August are popular events. In the autumn, the Dane County Farmers' Market is a great place to pick up local produce and crafts.
  • What are the best rentals or Airbnbs with a jacuzzi in Madison, WI?

    The best vacation rentals or Airbnb with a jacuzzi in Madison, WI are Quiet Eastside Madison Home, 1br Professionally Serviced Private Apartment and Luxurious Bbq And Pool House.

  • What are the best budget-friendly activities in Madison, WI?

    Madison has a lot to offer without breaking the bank. You can take a free walking tour of the city, enjoy a picnic lunch at the Olbrich Botanical Gardens, or visit the Chazen Museum of Art. There are plenty of free concerts and events held in the city park throughout the year.
  • What are the best restaurants with local dishes in Madison, WI?

    For a taste of Wisconsin, head to The Old Fashioned for classic comfort food. For a more upscale experience, try L'Etoile, known for its innovative French-inspired cuisine. You can't go wrong with the Wisconsin Brewing Company for a local craft beer.
  • What are the best walking or cycling routes in Madison, WI?

    The Capital City Trail is a popular walking and cycling route that runs for 20 km around the city. You can also enjoy a scenic ride along the Lake Mendota shoreline, taking in views of the university campus and the city skyline.
  • Are there pet-friendly attractions in Madison, WI?

    Yes, The Olbrich Botanical Gardens is a great place to take your furry friend for a stroll. Many of the city parks are also pet-friendly, and you'll find plenty of dog-friendly restaurants and cafes in the city.
  • What are the benefits of choosing a vacation rental in Madison, WI?

    Vacation rentals offer more space and privacy than hotels, making them ideal for families or groups. They often come with amenities like kitchens and laundry facilities, which can save you money on dining out and laundry costs.
  • What are the top sports attractions and facilities in Madison, WI?

    Madison is home to the University of Wisconsin Badgers, who compete in a variety of sports. The Camp Randall Stadium is a must-visit for any sports fan. You can also catch a game at the Kohl Center, home to the Badgers hockey team.

Popular destinations

Best Madison, WI holiday rentals with a balcony

Private Pool - Hot Tub - Sauna - Game Room - Pets - Madison, WI
No reviews

Private Pool - Hot Tub - Sauna - Game Room - Pets

apartment, Sun Prairie
This apartment in Sun Prairie is situated close to the Sun Prairie Historical Library and Museum and the Barrymore Theatre, with East Towne Mall and the Dane County Farmers' Market also within easy reach.
This spacious 297 square meter flat accommodates up to 16 guests and offers a private sauna, swimming pool, game room, and is ideal for those interested in fishing, horse riding, and cycling.
Studio Apartment At Cannery Square - Madison, WI
8.4 16 reviews

Studio Apartment At Cannery Square

studio, Sun Prairie
This Sun Prairie apartment is conveniently located less than 1 km from the Sun Prairie Historical Library and Museum and Angell Park Speedway, with Firemen's Park and the Sun Prairie Ice Arena within a 2.4 km radius.
This one-bedroom flat offers self-catering facilities including a fully equipped kitchen, in-unit laundry, and a balcony, sleeping up to two guests and boasting on-site parking and lift access.
The Wilson - Madison, WI
9.5 15 reviews

The Wilson

studio, Madison
This studio apartment in Madison offers a prime location, situated just 6.9 kilometres from Dane County Regional Airport and within easy reach of the Wisconsin State Capitol Building and Monona Terrace Community and Convention Centre.
Guests can enjoy air-conditioned comfort, complimentary WiFi, an on-site restaurant, a concierge service, and a kitchenette equipped with a dishwasher and microwave, alongside a sun terrace providing city views.
Entire 3 Bedroom With Fireplace - Sleeps 12 - Madison, WI
9.9 167 reviews

Entire 3 Bedroom With Fireplace - Sleeps 12

apartment, Sun Prairie
This Sun Prairie home is situated just a short distance from both the American Center and Token Creek Park, offering a convenient location for exploring the area. It has received excellent ratings for location, cleanliness, and overall experience.
The property offers ample space with three bedrooms and a floor area of 204 square metres. Guests can enjoy a range of amenities including a terrace, garden, barbecue grills, a fully equipped kitchen, and free WiFi.

Best Madison, WI holiday rentals with air conditioning

Studio Apartment At Cannery Square - Madison, WI
8.0 1 review

Studio Apartment At Cannery Square

studio, Sun Prairie
This studio flat is located directly on Sun Prairie square, offering immediate walkability to downtown shops and eateries, and is situated opposite a local coffee shop.
This 70 square metre flat accommodates two guests and features a well-equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace/balcony, parking, and is pet-friendly.
The Dylin Hotel | Premium Four Bedroom - Madison, WI
10 2 reviews

The Dylin Hotel | Premium Four Bedroom

apartment, Madison
This flat is situated in Madison's East Washington district, a short walk from Lake Mendota and Capitol Square, offering convenient access to downtown and the University of Wisconsin-Madison.
This 158 square metre residence accommodates up to 10 guests across four bedrooms, featuring a fully equipped kitchen, in-unit laundry, and onsite underground parking with EV charging available.
Entire Duplex Next To Waterfront - Madison, WI
9.3 579 reviews

Entire Duplex Next To Waterfront

apartment, Monona
This apartment is located in Monona, within 3km of Winnequah Park, Aldo Leopold Nature Center, and Esther Beach, making it a great base for exploring the area. It has excellent user, location, and cleanliness ratings, so you can be sure of a comfortable stay. This home sleeps up to eight people with four bedrooms and a sofa bed, making it suitable for families or groups of friends. The apartment comes with amenities such as a fully equipped kitchen, a terrace, a garden, a jacuzzi, a fitness centre, and a spa, plus parking and internet access.
The Wilson Unit G | Spacious Studio - Madison, WI
9.9 24 reviews

The Wilson Unit G | Spacious Studio

apartment, Madison
This recently renovated studio flat is located in downtown Madison, Wisconsin, within easy walking distance of numerous restaurants and breweries.
The self-contained apartment, sleeping two, boasts a full kitchen, separate dining area, and access to a shared roof deck overlooking the city; monthly parking is available for £150 at the building.
©2026 cozycozy.com