Holiday rentals with a pool in Dane County

Luxurious Bright Golfing Oasis!

Escape to our stunning, spacious home nestled on a beautiful golf course! Enjoy breathtaking views, abundant light and all the comforts of home. Perfect for golfers, families, or anyone seeking a relaxing getaway. This airy retreat offers ample space to unwind. Panoramic golf course views and outdoor four seasons room. Open living area with large windows. Fully equipped gourmet kitchen. Pristine bedrooms with plush bedding. Patio and huge backyard on hole 4, ideal for morning coffee and sunsets.

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

🔹Private fenced-in backyard w/ heated pool, hot tub, sauna, deck & fire pit 🔸Outdoor living w/ lounge seating, pool toys, & outdoor dining 🔹Large families & groups - 2 King, 6 Queen 🔸Game room w/ pool table, ping pong & arcade games 🔹3 min to Sun Prairie restaurants & shopping 🔸Basement gym w/ free weights & equipment 🔹Pickleball court in the garage 🔸You'll find "The Kohl Center, UW-Madison, Camp Randall Stadium, State Street, The Capitol, & The Alliant Energy Center" within 20min

Country Living/Downtown Access

A gracious getaway on a large, wooded lot in a country neighborhood that's just 10 minutes to Downtown Madison and UW campus. It's less to the Alliant Center and just 15 minutes to Epic taking Whelan Rd. This rental has four bedrooms and four bathrooms (three are en suite). Swim in the saltwater pool from Memorial Day weekend into September (weather permitting). Dog-friendly home (a small fee) with a fenced in yard. Relax on the large deck and pool-side patio or in one of three living areas.

Spacious GardenSetting Superhost 5miles toDowntown

Our licensed, peaceful Superhost home offers a lovely, spacious getaway just 5 miles from downtown Madison, and less than an hour to Wisconsin Dells Water Parks. . Featuring fast internet, an above ground pool, 4 LARGE bedrooms, 3 baths, a living room AND separate family room, a HUGE deck in our private, fenced in, beautifully landscaped yard. It’s perfect for families or working professionals. Enjoy modern comforts near top attractions, with ample parking in the driveway and on the street.

4 Bed, 3 Bath with Pool, Hot Tub, Gym, Fire Pit

Large beautiful home located just outside of Madison on the Lake Windsor Golf Course! Feel like you are at your own private retreat when you take in the gorgeous views of the course from the front porch, or when you are enjoying the private pool, hot tub, tiki hut, firepit, and hammock in the backyard. The detached garage boasts an incredible home gym with everything you need to keep up your normal exercise routine. The house is next to the interstate, so you will hear traffic noise.

Frank Lloyd W Inspired Estate w/Basement Speakeasy

Step into a world where mid-century modern elegance meets the adventurous soul of steampunk design. Inspired by the legendary architecture of Frank Lloyd Wright, the Lueders Road House is a sprawling three-lot estate designed for those who seek more than just a place to stay—they seek an unforgettable experience. ~ The Speakeasy ~ The All-Seasons Room ~ Game Night Upstairs & Basement ~ 2 Master Suites ~ Sunken Outdoor Kitchen & Fire Pit ~ Immaculate Grounds ~THE ULTIMATE LOCATION~

Luxurious BBQ and Pool House

Planning a pool party, summer barbecue, or relaxing getaway near Madison? This modern 3-bedroom, 2.5-bath home sits on a quiet 3/4-acre wooded lot just 15 minutes from downtown. Enjoy a private swimming pool, year-round hot tub, large yard, and wrap-around deck with gas grill and outdoor dining space. With plenty of room to relax indoors and out, it’s the perfect spot for families, friends, or groups looking to unwind, entertain, and enjoy everything Madison has to offer.

Private yet close to everything!

Our 900 sqft basement apartment features a master bedroom, connecting kitchenette/sitting room, and bathroom. We are a 20-minute drive to the UW campus, Capitol Square, and Dane County Airport—minutes from Middleton Pheasant Branch Conservancy for hiking and biking. Madison and Middleton consistently win "Best Places to Live" awards for quality of life. As past Superhosts, we are excited to start hosting again after COVID!

Serviced Two Bedroom Apartment in Central Madison

Nestled in 7 wooded acres, our two bedroom furnished apartment is 900 square feet with plenty of room to fit a family. With our full-size furnished apartments, top notch customer service, free amenities, and flexibility in renting, our value makes it an easy choice to call Countryside home.

Private 2BR Apartment Centrally Located in Madison

Located just minutes from both downtown and the west and east sides of Madison, WI, Countryside Corporate Apartments makes short-term fully furnished housing easy, flexible, and stress free. Guests can rent for specific dates, or weekly/ monthly, even if your end date is uncertain.

Centrally Located Two Bedroom Serviced Apartment

Located just minutes from both downtown and the west and east sides of Madison, WI, Countryside Corporate Apartments makes short-term fully furnished housing easy, flexible, and stress free. Guests can rent for specific dates, or weekly/ monthly, even if your end date is uncertain.

1BR Professionally Serviced Private Apartment

Located just minutes from both downtown and the west and east sides of Madison, WI, Countryside Corporate Apartments makes short-term fully furnished housing easy, flexible, and stress free. Guests can rent for specific dates, or weekly/ monthly, even if your end date is uncertain.