Villa holiday rentals in Wisconsin

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 at this 2-acre nature conservancy. Soak in the outdoor hot tub with the best, unobstructed views of the sky. SAUNA (Add-On) Outdoor Finnish wood burning cedar sauna. Seats 10+ persons. $100 per reservation for unlimited sauna use. This includes firewood, extra towels and additional cleaning personnel. Water buckets available seasonally.

Value · Family · Amenities

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.

Location · Family · Checkout

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.

Location · Family · Cleanliness

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 and a firepit. 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.

Family · Location · Comfort

Mid-Century Lake Michigan Escape | Private Beach

Wake up to the sun rising over Lake Michigan. Wisconsin Lake Escape is a one-of-a-kind 1959 mid-century lakefront home perched above Lake Michigan, with breathtaking 180° water views and your own private beach below. Designed by noted American architect John Randal McDonald, the home features dramatic floor-to-ceiling glass, three fireplaces, expansive gathering spaces and unforgettable views. Come for the lake. Stay for the people you came with.

Family · Location · Beach

Road America Oasis: 25 Acres, Hot Tub & Orchard

Race weekend retreat on 25 quiet acres — soak under the stars in the hot tub, cook for the crew in a chef's kitchen, and unwind by the fireplace. 15 min from Road America and Elkhart Lake. Hot tub, fire pit, walking trails, apple orchard, in-home gym, and 3-season sunroom in the woods. 4BR/2.5BA luxury villa sleeps 8. Quiet, private, and built for relaxation — perfect for race teams, race fans, and groups looking for a luxurious summer getaway.

Family · Value · Hospitality

Perfect Paradise | 4BR Lakeview Condo w/ Jacuzzi

Perfect Paradise by Great Lakes Getaways! Unwind in this spacious 4-bedroom, 3-bath beachfront condo—perfect for families or groups. Enjoy a luxurious master suite with a 2-person jacuzzi tub, cozy gas fireplace, and private balcony overlooking the courtyard and Lake Michigan. With 7 beds, a fully stocked kitchen, in-unit washer/dryer, and stylish living spaces, comfort and convenience come standard. Your relaxing lakeside getaway starts here.

Family · Value · Check-in

Villa Near Lake Geneva, close to Lake

Our comfortalble one bedroom villa has got you covered on your next getaway! Nearby, you will find a local ski hill, plus canoeing and ziplining outfits. At the resort, you will have access to two championship golf courses, pools, seven on-site restaurants, a spa, and more - all serviced by a local shuttle service. With the additional in-suite washer/dryer and full kitchen, you will be sure to call this property your home away from home!

Value · Family · Accuracy

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!

Family · Location · Check-in

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.

Location · Value · Hiking

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.

Family · Value · Laundry

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!

Location · Family · Sleep quality