Holiday rentals in Monona

4.97 out of 5 average rating, 204 reviews

Loft in McFarland

#301 Private Apartment in Historic McFarland House

*** Our 2nd Floor is being remodeled throughout 2025 adding 4 more units to the old McFarland House This newly remodeled unit is located in the attic of the Historic McFarland House, built in 1857 in the community that bears its name. Nestled in our small suburban downtown, this unit is perfect for travelers visiting the Madison area or nomads making a pit stop in the mid-west. Only 8mi to campus or a quick commute to the capitol, McFarland is an easy exit off multiple highways and interstates.

4.96 out of 5 average rating, 74 reviews

Wonderful 3 bed home close to downtown & the lake

Fully renovated home in the heart of Madison! Located on a quiet street near Lake Monona, parks, & just one block from the Lake Monona bike trail. Home features a beautifully updated kitchen & bath along w/2 spacious living areas. Enjoy the screened porch overlooking a fully fenced yard with mature trees, perfect for outdoor relaxation. Amenities include a gas grill, off-street parking, laundry facilities, high-speed internet&cable TV. With hosts nearby, assistance is always available if needed.

Guest suite in Sun Prairie

4.89 out of 5 average rating, 370 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.

4.95 out of 5 average rating, 389 reviews

Guest suite in Madison

Cottage Suite + Whirlpool Tub.

This Suite is perfect for 1-4 people seeking convenient proximity to most things Madison 10-15 minutes to downtown. *Freshly remodeled guest dedicated- full 1st floor private suite. You will enjoy a bright- enclosed front porch & welcoming pergola in back. *Please note: 2nd floor is a seperate apartment. Fast WIFI●Infrared Sauna●2 Smart TV 's●Full Kitchen●Washer/Dryer●Dishwasher ●Off-Street parking●Quiet neighborhood ●Reverse osmosis H²O●Smart lock's●Jacuzzi tub/shower●Shampoo/Cond./Bodywash

5 out of 5 average rating, 32 reviews

Welcome Home-Convenient to Everything Madison!

Classic, clean, comfortable and convenient to all things Madison! Welcome Home to Monona, WI, a small, family-friendly and peaceful community surrounded by Madison. Minutes to UW-campus and downtown Madison. 2 blocks to the Monona Lake bike path. This ideally situated family-friendly home is newly renovated and newly furnished. Enjoy the new outdoor patio w Weber grill, Nespresso coffee bar, 2 lg screen smart TVs, wifi, rec room with games/foosball/chalk-doodle board and a 2 stall garage!

4.98 out of 5 average rating, 206 reviews

Home in Marquette

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).

4.87 out of 5 average rating, 279 reviews

Home in Madison

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.

4.88 out of 5 average rating, 56 reviews

Renovated 4 BR Home Near Madison

Relax with the whole family at this peaceful place to stay! Located right on the Lake Monona bike path and 10 minutes from downtown Madison, this is the perfect stay for couples, families, and groups of friends to see all Madison has to offer. 3 minute walk to various bars and restaurants in Monona! The home is equipped with 3 55'' smart tvs, a ping pong table, basketball hoop, and 4 bedrooms with 5 mattresses including 2 king beds. A high chair and/or Pack N Play available upon request.

Superhost

4.89 out of 5 average rating, 103 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!

4.99 out of 5 average rating, 211 reviews

Guest suite in Middleton

Quiet sunlit studio near vibrant downtown

This architect-designed studio is bathed in natural light, with skylights and a breakfast nook with a wrap-around window. Featuring an upscale bathroom with a walk-in shower, this comfortable space has all the amenities perfect for a quick weekend getaway or a week-long business trip. The studio adjoins a house and is up a flight of stairs through a separate outdoor entrance. Located just up the hill—a 5-minute walk—to Downtown Middleton and a 15-minute drive to UW and Downtown Madison.

Guest house in Sun Prairie

4.98 out of 5 average rating, 370 reviews

Charming Milkhouse Cottage, minutes from Madison!

Welcome to The Milkhouse Cottage! Serving as an original milkhouse from the late 1800s on our pre-civil war farmhouse property, you will feel the timeless elegance of the original character and the beautiful french cottage decor. Perfect for couples, travelers, or business persons -- come and unwind in the scenic heartland countryside and rustic elegance, all with the convenience of location -- we are a quick 15 minute drive from the airport and all that Madison has to offer!