Family-friendly holiday rentals in Lake Monona

4.98 out of 5 average rating, 285 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.

4.98 out of 5 average rating, 280 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).

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.

4.9 out of 5 average rating, 136 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!

4.96 out of 5 average rating, 665 reviews

The outdoor area of the home is visible, featuring a spiral staircase leading to a deck with a covered area. A hot tub is positioned on the patio below, surrounded by lush greenery and string lights hanging above, providing a relaxed and inviting ambiance.

Guest suite in Madison

Downtown Lake Monona Haven | SUPs, Hot Tub & Sauna

Stay in your private 3BR, 2BA section of our lakefront home. Paddle from the dock, relax in the hot tub or sauna and enjoy mornings on the balcony with coffee. You’re moments from Willy Street restaurants and right on the bike path. Inside, find a full kitchen, comfy living spaces. Two parking spots included. Spend days on the water or exploring the city and evenings grilling or roasting marshmallows by the fire. Paddleboards included. Pontoon rental available in warmer months.

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, 126 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

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, 105 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, small 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.

4.99 out of 5 average rating, 144 reviews

A bright living space features a gray sofa adorned with a decorative pillow, accompanied by a rounded coffee table. A dining area with colorful chairs and a wooden table is visible in a well-lit room. Natural light filters through the windows, highlighting the modern interior.

Bungalow in Monona

Retro Charm Near DT Madison & Lake Monona

Experience the best of Wisconsin’s Capital City in this newly remodeled 1930's bungalow in one of Madison’s most desirable neighborhoods. Rent a BCycle e-bike and take it for a spin on the famous 13-mile Lake Loop, just steps from our front door. Splash in Lake Monona at nearby Schluter Beach. Treat yourself to an ice cream cone at the retro ice cream parlor. When you're ready to shop or hit the farmer's market, downtown Madison is an easy 15-minute drive.

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.

4.89 out of 5 average rating, 140 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

4.97 out of 5 average rating, 170 reviews

The kitchen features white cabinetry with sleek hardware and a large sink positioned under a window. A tile backsplash adds a modern touch. Ample counter space is available for meal preparation, and kitchen essentials are organized in drawers.

Home in Sun Prairie

Nothing Else Like It!

There is absolutely nothing else like it available, and you’ll agree as soon as you step foot inside! This beautifully designed home makes your stay comfortable with it's high end furnishings, bedding, towels, mattresses and dishes. Kick back and relax in this calm, stylish space. Fully fenced backyard great for dogs, entertaining and room for kids to play. Private work space available too! All bedrooms have room darkening shades!

4.99 out of 5 average rating, 175 reviews

Farm stay in Monroe

The Dairy at the Wegmueller Farm

Welcome! You are about to experience life on an active 4th-generation farm nestled in the rolling hills of Green County. Meet the cows, feed the pigs, befriend a horse, or just enjoy the relaxing and peaceful serenity of rural Wisconsin farm life. Located less than five miles from Monroe, this home away from home is close enough to all that Monroe & the surrounding community has to offer, but still has room to stretch your legs.

4.88 out of 5 average rating, 101 reviews

A comfortable living room is showcased, featuring a blue sofa and two armchairs. A coffee table sits in the center, with a plant atop. A fireplace is visible, along with windows allowing natural light. A mirror and wall art enhance the room's décor.

Cottage in Monona

Cheerful 3-bedroom cottage 2 blocks from the lake

Stay in our cheerful cottage just two blocks away from the lake! Enjoy a spacious front yard with a great back patio to grill out on. Less than 12 minutes away from downtown Madison, this is the perfect stay for couples, families, and groups of friends. There are two bedrooms with full mattresses on the first floor and a master bedroom with a king bed on the second floor. A high chair and/or Pack N Play available upon request.

A cozy three-season sun porch features a gray sofa adorned with cushions and a small, dark ottoman. A wall-mounted electric fireplace provides warmth, while string lights and large windows allow for ample natural light. Various plants are positioned around the room, enhancing the inviting space.