Villa holiday rentals in Wisconsin

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Top-rated villa rentals in Wisconsin

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Villa in Gillett

4.85 out of 5 average rating, 94 reviews

Cedar Springs Reserve, a 4 Season Lakefront Escape

Welcome to Cedar Springs Reserve. This lake front property is 137 acres, and surrounds 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.

Guest favourite

Villa in Crandon

5 out of 5 average rating, 22 reviews

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.

Guest favourite

Villa in Plymouth

4.98 out of 5 average rating, 40 reviews

Luxury Retreat near Road America

Private, luxurious home on 25 serene acres. Relax, entertain, or enjoy activities in legendary Elkhart Lake, Road America, Whistling Straits, Black Wolf Run or nearby Lake Michigan. Soaring ceilings and natural light, stocked kitchen, fireplace, apple orchard, outdoor fire pit, large yard with private hunting cabin. Our Villa is a spacious 4-bedroom 3-bath home located 10 mins from Road America, 15 mins from Kohler spa, 25 mins from Whistling straits golf course and 10 mins from Elkhart lake.

Superhost

Villa in Wisconsin Dells

4.92 out of 5 average rating, 24 reviews

Ground level Poolside Villa on Lake Delton

Have it all within your reach at this beautiful pool side Villa! 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!

Villa in Racine

4.76 out of 5 average rating, 80 reviews

Wisconsin Lake Escape - A Mid Century Gem

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!

Guest favourite

Villa in Benton

5 out of 5 average rating, 12 reviews

The stay with the story

We transformed a stone farmhouse into a spacious villa. Our little slice of heaven is just off the beaten path. The villa offers enough beds for twelve people and three additional pullout beds. There are also two sofas, two loveseats and air mattresses can be made available for larger groups. Falling in love with this amazing place? We totally understand. Ask about our special wedding packages which include exclusive rental pricing for the villa, cabin, barn and our sprawling acreage.

Superhost

Villa in Elkhart Lake

5 out of 5 average rating, 4 reviews

First Floor Queen with Single Pull-out

WELCOME RACE FANS AND VACATIONERS!!!! The Victorian Inn is located along a picturesque freshwater lake and within walking distance to exciting events and adventures!Our rooms offer easy access to an indoor pool, outdoor pool, fresh water lake, and so much more! Victorian Inn is situated in the heart of downtown Elkhart Lake near several specialty shops and restaurants. We're also just 2 miles from Road America, 8 miles from Kettle Moraine State Forest, and a short drive to PGA golf courses!

Guest favourite

Villa in Racine

4.95 out of 5 average rating, 141 reviews

Gorgeous historical mansion on Lake Michigan

Welcome to the historic Carpenter House! This is an opportunity to stay in a former Bed & Breakfast overlooking Lake Michigan. A historical neo-classical home built in 1896 with tons on history. The home was completely renovated a few years ago. Wake up and sit on the front porch and enjoy the beautiful view of Lake Michigan. The house is located in the historical district in Racine. The home boasts a ballroom on the 3rd floor that is suitable for small events and a private cute garden.

Superhost

Villa in Lake Geneva

4.77 out of 5 average rating, 22 reviews

Villa Near Lake Geneva | Close to the Airport

Looking for a cozy getaway to Lake Geneva? Our comfortable two bedroom villas have got you covered! 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, indoor and outdoor pools, and horseback riding - all catered 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!

Guest favourite

Villa in Danbury

4.92 out of 5 average rating, 13 reviews

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.

Guest favourite

Villa in Sheboygan

5 out of 5 average rating, 35 reviews

Lovely Lake Lookout - Cozy Condo Steps from Lake

Lovely Lake Lookout by Great Lakes Getaways! 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. Your lakeside escape starts here!

Guest favourite

Villa in Hales Corners

4.92 out of 5 average rating, 36 reviews

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!