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 - Game Room - 20 min DT

🔹Private fenced in backyard w/ heated pool w/ pool toys & HOT TUB 🔸Outdoor living w/ lounge seating on the deck, gas grill, outdoor dining & fire pit 🔹Sleeps families & groups - 3 King, 4 Queen 🔸Game room w/ pool table, smart tv, board games, & gas fireplace 🔹5 min to Sun Prairie restaurants & shopping 🔸Pets welcome 🔹Highchair & pack n’ play on site 🔸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.

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.

Outdoor Oasis: Luxe Flat in Mt Horeb!

Serene Setting | Poolside Relaxation | Group Getaway Get ready for fresh air and endless fun at this inviting 3-bedroom, 1.5-bath vacation rental flat! This Mt Horeb retreat treats guests to laid-back luxury — soak in the private pool, savor freshly grilled feasts on the patio, and settle around the fire table for peaceful evenings under string lights and starry skies. With room for everyone — including your furry friends — this property is built for relaxation and lasting memories.

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

Hosting a summer barbecue, a pool party, or just looking for a relaxing getaway with your friends? The unique combination of indoor and outdoor space provides something for everyone. This is a modern, spacious, and luxurious 3 bedroom, 2.5 bath home, conveniently located 15 minutes from downtown. Situated on a 3/4 acre lot, this house is fully equipped w/ premium amenities for your friends and family:Swimming pool, hot tub, big yard, deck with a gas grill and dining area

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.

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.