Villa holiday rentals in Wisconsin

Spacious Three Story w/ Huge Decks on Clear Lake

Relax or recreate with the best that Northern Wisconsin has to offer! Take in every sunset from 3 different decks with this brand new Gulf Coast inspired lake home on private, full recreation Clear Lake in the Nicolet National Forest! Whether you come to swim, snowmobile, race or relax, this home has you covered. The home is 3 levels and houses over 3500 square feet with 4 large bedrooms (3 w/ access to the decks and lake views) and 4 full bathrooms. 12 beds that sleep a total of 19 occupants.

Wisconsin Lake Escape - Villa with Pvt Beach

Designed by American Architect John Randal Mcdonald in 1959, this lakefront Mid century home, perched on a bluff on Lake Michigan boasts spectacular sunrises, breathtaking 180 deg views and steps to a private beach! This designer home is a gem to recharge, escape, a honeymoon destination, a retreat, a family reunion, or a small getaway with other couples!! And if you're a digital nomad, to work in a stunning location. The sound of waves, 3 fireplaces and outdoor firepits, will rejuvenate you!

Luxury Lake Geneva retreat (hot tub, Sauna) 2-Acre

Experience Lake Geneva at its best at this centrally located, secluded Elizabethan Tudor style retreat. This property gives a new meaning to Forest Bathing! You will be surrounded by some of the largest and oldest trees in Wisconsin at this 2-acre nature conservancy. Soak in the outdoor hot tub with the best, unobstructed views of the sky. SAUNA (Paid Add-On) Outdoor Arctic wood burning cedar sauna. Seats 8-10 at a time. Available as Add-On. $40 per person minimum $250 and Maximum $400.

Cedar Springs Reserve, a 4 Season Lakefront Escape

Welcome to Cedar Springs Reserve. This property totals 137 acres, and borders 398 acres of shallow lake and wetlands. Winter is a time of quiet solitude. Spring a time of renewal. Summer a riot of growth with eagle, beaver, otter and loons to observe. If you enjoy fishing there are perch bass and bluegill to be teased out of the lilies, but you will have to work hard to find them. Kayaks are provided for your exploration. Boat rentals and sand beaches at Shawano lake not far away.

Spacious Family Villa w/ Decks in Chilton!

Pets Welcome w/ Fee | 3 Kitchens | 'Through The Woods Vacation Rental' | 1 Mi to Lake Winnebago Gather loved ones and experience an unforgettable retreat at this villa in Chilton, WI! Boasting 4 bedrooms, a sleeping nook, 4.5 bathrooms, and 5,328 square feet, this impressive property offers plenty of space for your entire crew! After taking the kids to the petting farm, exploring apple orchards, or dining at a supper club, top off the evening with stargazing around the fire pit.

Lovely Lake Lookout - Cozy Condo Steps from Lake

Lovely Lake Lookout by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026. Unwind at this cozy 2BR/2BA condo just moments from Lake Michigan. Enjoy evenings by the gas fireplace, dine al fresco on the private patio, and explore nearby shops and restaurants. Fully stocked kitchen, comfy spaces, and local tips for watersport adventures. Managed with care by a local team—no waterpark access, but so much more to love.

The Water's Edge Villa

This 3-bedroom, 3-bath lake rental is the perfect spot for a memory-filled retreat. This home has all the ideal lakeside amenities: an outdoor kitchen with a gas grill, a boat dock with direct Minerva Lake chain access, kayaks, and plenty of outdoor seating areas! When you’re not on the water, play the 9-hole disc golf on the 8-acres of private land across the road, head out to take on the ATV and snowmobile trails, or test your luck at nearby casinos.

Whistling Straights, EAA, NFL Draft, Road America

Incredible Lake Views from our wrap around deck and large lower patio! Private 1.5 acre Villa. 3 Fire Pits. 2 Indoor Fireplaces. Perfect location for Golf Weekends, Packer Games, NFL Draft, EAA, Racing Weekends and Friend Gatherings! Gourmet kitchen. Wood Fire Pizza oven. Just 5 Minutes off the Interstate! Witness incredible sun/moon rises over the lake, bird watching, wildlife, yard games and sea glass hunting at Hika Bay beach!

Pine Forest Villa w/hot tub 5 min from Lake

Enjoy this gorgeous home just 30 miles from Wisconsin Dells, located within walking distance to beautiful Castle Rock Lake and right next to Northern Bay Resort. It’s only 20 minutes from the renowned Sand Valley Golf Course, offering plenty of activities nearby! Explore Buckhorn State Park, go fishing, hiking, or visit the ATV park. In winter, enjoy snowmobile trails and skiing close by. Nestled on 1.75 acres surrounded by pine trees.

Wandering Waves | Beachfront Lake Michigan Stay!

Wandering Waves by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026. Wake up to sweeping Lake Michigan views in this stylish 2BR/2BA beachfront condo! Just steps from the sand, you’ll enjoy sunrise mornings, wave-filled nights, and unbeatable beach access. Inside, a modern open layout offers a fully equipped kitchen, cozy living area, and private patio with serene water views.

Ground level Poolside Villa on Lake Delton

Step out from your private screened in porch to soak up some sun on the pool deck or enjoy some time on one of the 2 private beaches! The property sits on 15 acres of tall pines for beautiful seclusion while boasting a large heated swimming pool, 2 private beaches, a kid’s playground, volleyball court, horseshoe pits, & private dock. This peaceful space is private when needed, yet only minutes from all the Wis Dells attractions!

Beautiful 6 bedroom with Heated Pool & Jacuzzi

Relax with the whole family at this peaceful place to stay right in the middle of beautiful Whitnall Park. You won't find a more peaceful view of the woods and park. Our beautiful home has a large heated pool with brand new 6 person jacuzzi. Brand new Kitchen and updated bathrooms. Master suite is very romantic with steam shower, jacuzzi tub, and luxury bed and fireplace. Family Friendly OR Romantic Getaway!