Vacation rentals with a pool in Dane County

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

Location · Value · Bathroom

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

Location · Value · Hospitality

Architectural Retreat, Speakeasy, Opt In Pool Heat

Step into a private architectural retreat where Frank Lloyd Wright-inspired design meets a hidden speakeasy lounge, immersive entertainment spaces, and resort-style outdoor living. Designed for unforgettable gatherings, this one-of-a-kind estate blends timeless architecture with modern luxury, creating the perfect backdrop for relaxing weekends, celebrations, executive retreats, and elevated group getaways. Optional Pool Heating @ an additional daily fee of $50 & must add on full length of stay

Family · Location · Decor

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.

Location · Family · Hospitality

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.

Location · Family · Backyard

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.

Family · Outdoor spaces · Hospitality

Private yet close to everything! NEW

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!

Family · Location · Bathroom

Professionally Serviced Private 1BR 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.

Value · Location · Kitchen

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.

Location · Value · Laundry

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.

Value · Location · Bathroom