Family-friendly holiday rentals in Lake Monona

4.98 out of 5 average rating, 284 reviews

A comfortable living area features a black leather sofa adorned with red and yellow pillows. A wooden coffee table sits in front, and a colorful area rug adds warmth to the space. The background reveals a well-lit kitchen with modern fixtures.

Home in Madison

Charming Campus Area Home • Entire Home Near UW

Steps to Camp Randall & an easy walk to UW–Madison! Spacious home for up to 10 guests with a comfortable layout, multiple bedrooms, full kitchen, and inviting gathering spaces. Enjoy the back patio—perfect for unwinding after a day on campus or exploring the city. Ideal for Badgers game weekends, family visits, and group stays. Please note: during football weekends, the host may use the garage and part of the driveway for tailgating; parking may be shared. Cleaning fee $150. No pets or smoking.

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Guest suite in Sun Prairie

A two-story home with a mix of stone and wood siding sits on a grassy lot. Large windows allow natural light inside. A paved driveway leads to the garage, with trees and a view of open land in the background.

4.89 out of 5 average rating, 447 reviews

Entire Lower Level, Countryside Garden Suite

Welcome to our home! We have upgraded our Garden (lower) Level to host travelers much like ourselves and long-term guests. The view of our backyard is incredible! You will find yourself lost in the country, yet less than ten minutes from all the excitement that Madison has to offer. Along with a private drive and entrance, you will have 1,000 square feet of comfort all to yourselves. This property is perfect for a quiet getaway we all need from time to time. All designed with you in mind.

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4.97 out of 5 average rating, 276 reviews

Home in Madison

Lakeview Loft - Downtown Madison

Stay in the heart of Madison, enjoying exclusive access to our 3rd floor suite with lake views. Located on a quiet street along the Lake Loop bike path/Lake Monona, and close to Willy Street (0.3 mi), the Sylvee (1.1 mi), the Capitol (1.7 mi), Monona Terrace (1.6 mi), and Camp Randall (3.3 mi). Self check-in with keypad and ample parking. Wifi is over 500 Mbps download/upload speeds. #ZTRHP1-2022-00022 Note: Loft is accessed by 3 flights of stairs! Space has coffee bar only (no kitchen).

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A serene outdoor patio area is shown, featuring a cobblestone surface surrounded by well-maintained gardens and tall, manicured hedges. A central fountain adds visual interest, while a dining table and chairs invite relaxation. Potted plants and seasonal flowers enhance the garden's charm.

4.88 out of 5 average rating, 319 reviews

Private apartment -2 Beds, Kitchen Office, Sunroom

COVID CLEANED Private Garden Apartment. Feel at home in your private lower level living space. Our home is surrounded by beautiful landscaped gardens and patios. We are located near the lake, on the lake bike loop, in the heart of Madison. Relax outside, enjoy dinner on the patio or have a bonfire. Venture out on a bike ride to the farmer's market on the Capital Square, or visit Monona Terrace, State Street, Olbrich Gardens or the Alliant Energy Center; just a short distance away.

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An outdoor dining area is featured on the deck, consisting of a wooden table surrounded by black wicker chairs. A small potted plant adds a natural touch. The scenic view of the river, a bridge, and a private dock can be seen in the background.

4.91 out of 5 average rating, 134 reviews

Madison Lakefront Oasis in the Heart of Madison

Enjoy all that Madison has to offer from this beautiful lakefront property. BRING YOUR BOAT, our private dock on Yahara River has 3 slips with access to both Lake Monona & Lake Waubesa. Central location offers multiple restaurants, shops & public boat launch all within walking distance. Breath-taking sunsets over the lake. Quick 5-10 minute commute to downtown Madison, UW-Campus, Hospitals, Alliant Energy & Sylvee, State Street, hundreds of other Madison attractions east or west side!

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A spacious living area features a vintage brick fireplace as the focal point, accompanied by a wall-mounted television. Comfortable seating is provided by a green couch and chairs, while a coffee table sits atop a plaid area rug. A dining table is visible through the large window.

4.97 out of 5 average rating, 142 reviews

MCM Ranch by Lake & DT Madison

Immerse yourself in the best of mid-century living in this true-to-era retro ranch. Located across the street from picturesque Lake Monona, this is the perfect spot to come home to after exploring the Madison area. Enjoy coffee and board games in the expansive nature-themed living room; rest in any of the three comfy bedrooms; lounge on the front porch or backyard or whip up a meal in the 1950s kitchen. This is more than just an Airbnb; this is an experience you won't forget!

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4.91 out of 5 average rating, 157 reviews

This spacious bedroom contains a comfortable bed dressed in white linens, with a decorative throw and pillows. Natural light filters through the window, illuminating a wooden dresser and bedside tables. A textured area rug adds warmth to the room, creating a cozy atmosphere.

Home in Fitchburg

Comfortable Madison Area Retreat In The Trees

Tri-level duplex centrally located in Fitchburg. Nestled in a quiet residential neighborhood backing up to a small patch of woods for privacy. Feel away from it all with the sights and sounds of nature yet close to all the modern conveniences. Enjoy separated living spaces, a fully equipped kitchen (per WI health code, edible cooking supplies are not allowed–we do provide untamperable salt and pepper), 3 bedrooms, 2 full bathrooms, fully stocked laundry room and attached garage!

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A spacious living area is arranged with two red sofas flanking a central wooden coffee table. A patterned couch with black and white designs provides additional seating. Natural light enters through large windows, illuminating the warm wooden floors.

4.94 out of 5 average rating, 125 reviews

It's called the Annex-right next door to us!

The house is located in a quiet and friendly neighborhood. Community parks and city pool within 2 blocks of of the home. Close to all schools, library, parks and bike paths. Very safe and enjoyable neighborhood. Many good restaurants in the area and lots of things to do in the area Two bedrooms are upstairs with its' own bathroom. House is air conditioned and has a full and complete kitchen. The washer/dryer are located in the basement and guest have full access to it

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4.92 out of 5 average rating, 279 reviews

Cabin in Merrimac

Lakeview Cabin> Unique Mid-Century Tucked in Bluff

Nestled in the bluffs of Caledonia, this cabin offers a true Wisconsin experience! Floor to ceiling windows boast amazing water views of Lake Wisconsin, all while you reside in the charm of the mid-century architecture of this cabin. Minutes from the bluffs of Devil's Lake which offer some of Wisconsin's best hiking, biking, walking trails, and swimming! Plus, a short drive from Baraboo or Wisconsin Dells, where you can check out shops, restaurants and local attractions!

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An open floorplan connects the modern kitchen and dining area to the inviting living space. Natural light fills the room through multiple windows. A spacious dining table is positioned near the kitchen, while comfortable seating is arranged in the living area.

4.94 out of 5 average rating, 102 reviews

Centrally located 4 Bedroom beautiful home

Renovated 4 bedroom/2 bath home with spacious open floorplan. Home is close to downtown Madison and centrally located. Lake Monona access, & on Madison's #1 bike trail, Lake Monona Loop within walking distance. Large backyard with gas grill, 3 season porch, off-street parking, laundry facilities, high speed internet & TV. The newly renovated kitchen is great for preparing meals. This is the ideal location to explore all that this amazing region has to offer.

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A spacious living area is furnished with light grey sectional sofas positioned around a wooden coffee table. Natural light filters in through large windows, complemented by dark curtains. A dark area rug adds warmth, with decorative items displayed on a nearby shelf.

4.9 out of 5 average rating, 136 reviews

Comfy 3 bedroom Cottage

It would be our pleasure to host you during your next adventure to Madison! You will have access to the entire house containing 3 bedrooms & 1 bathroom. Quick access to everything Madison! UW, Alliant Energy Center (Cross-fit Games), Monona Terrace (Ironman), Epic and Dane County Regional Airport. Drive times: Beach - 3 min Olbrich Gardens - 7 min Alliant center - 10 min Capitol/Downtown - 13 min Camp Randall Stadium - 15 min Airport - 15 min

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