Villa vacation rentals in Madison

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Top-rated villa rentals in Madison

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A glass gazebo features a comfortable green sofa and two round, brightly patterned chairs, arranged around a small table. Natural light fills the space, highlighting views of the surrounding greenery and outdoor hot tub through the large glass panels.

Villa in Delavan

4.9 out of 5 average rating, 59 reviews

Luxury Lake Geneva retreat w/hot tub on 2-acres

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. Feel like skinny dipping? The only creatures that will be watching are the abundant variety of wildlife. Minutes away from all three lakes and all the action

Top guest favorite

An open living area is featured, showcasing a cozy sofa adorned with decorative pillows. A patterned chair with the word 'home' is positioned next to a small wooden table, which holds a few items. The area is brightened by natural light from sliding glass doors.

Villa in Galena

4.98 out of 5 average rating, 134 reviews

Semi-private Pool, King Bd, Near Spa, Golf, Trails

✓Near hiking trails & paved walking trails ✓Stonedrift Spa, 3 min drive ✓North Course & Driving Range, 2 min drive ✓Downtown Galena, 15 min drive ✓Semi-private outdoor pool, steps away ✓Well equipped kitchen w/modern appliances ✓Gas grill ✓Smart TV on each level w/Roku & YouTube TV ✓Computer desk ✓Fireplace w/supply of firewood ✓Queen sofa bed ✓2 Full baths ✓Owner's Club access ✓Indoor pool ✓Lake access ✓Chestnut Mountain (Ski & Zipline), 25 min drive ✓Guest favorites: "cleanliness & comfort"

The exterior of the Italian Villa is framed by lush greenery and trees, showcasing a warm beige stucco facade. A charming front entrance is highlighted by a decorative archway, flanked by windows with blue shutters, and adorned with flowering plants along the pathway.

Villa in Rockford

4.5 out of 5 average rating, 6 reviews

Rockford’s Historic Villa + CLOSE to city!

Experience the timeless elegance of Jesse Barloga's renowned architecture from the 1920s at our spacious and centrally located historic residence in Rockford, Illinois. This exquisite Italian Villa, nestled in the charming Brown Hills area near the Rock River, offers unparalleled proximity to the Rock River bike path, YMCA, and Nicholson Conservatory and is close to Downtown life. Immerse yourself in the convenience of accessing the region's finest attractions, many just a short stroll away!

Superhost

A cozy living room features two sofas, a lounge chair, and a stone-surrounded gas fireplace. Natural light filters in through a nearby window, creating a warm ambiance. Open shelving displays decorative items, and the kitchen area is visible in the background with modern appliances.

Villa in Wisconsin Dells

4.92 out of 5 average rating, 26 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!

Guest favorite

A spacious villa is set against a backdrop of rolling hills and cloudy skies. The exterior features a blend of wood and grey siding, with a welcoming porch that extends around the lower level. Chickens can be seen freely roaming on the lush green lawn.

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.

Guest favorite

The inviting exterior of a townhome is featured under a starry sky, with warm lighting illuminating the pathways and landscaping. The home showcases a quaint porch and large windows, contributing to its welcoming appearance. A lush lawn surrounds the structure, enhancing the property's charm.

Villa in Galena

4.98 out of 5 average rating, 44 reviews

Cozy On In w/ Us! At this stunning townhome!

Spacious 2 bedroom/2 bath bright end unit townhome in the sought after Walnut Hill Golf Villa community. Close to the North Golf Course and the driving range, this home is within walking distance to Eagle Ridge Resort and Stonedrift Spa. Wood burning fireplace, private back deck for grilling and bird watching. The home comes with not only Owners' Club passes but also entrance to a semi-private pool, where you can always find a chair, exclusively for guests of this villa group. Come Join Us!

The living area features a gas fireplace, a white sofa with decorative pillows, and a wooden entertainment unit. A flat-screen TV is mounted above the fireplace. The open kitchen area is visible in the background, equipped with white cabinets and essential appliances.

Villa in Lake Geneva

4.9 out of 5 average rating, 61 reviews

Interlaken Villa w/ Patio, Steps to Ridge Resort!

The perfect retreat begins at this 1-bed, 1-bath vacation rental! Nestled steps to the Ridge Hotel - a short walk to Lake Como - and minutes from Lake Geneva and the downtown shops and restaurants, this villa makes the perfect home base for your stay. Spend your day sipping wine at the Apple Barn Orchard & Winery or hit the links at the Majestic Oaks Golf Course. After, return to this tastefully furnished villa and enjoy a home-cooked meal and a movie night with your loved ones!

Top guest favorite

An illustrated vintage-style poster features a close-up of a wolf’s face, evoking a sense of wilderness. The background shows a serene natural landscape, with text indicating it represents five-star lodging in Lake Delton, Wisconsin.

Villa in Wisconsin Dells

4.94 out of 5 average rating, 35 reviews

Dells, Wolves Lodge B&B, kayaks, Mini SPA

The Original treetop master bedroom and mini spa bath. Desirable location on trendy Lake Delton. Note: Mirror lake , and Devil’s lake beaches very near by. Mini SPA FOR HER spa kit (see theme room photos) SPA setup, massage recliner, spa designed shower area, music, Egyptian cotton sheets, robe, spa products. Private property, wildlife decor, full kitchen, WiFi, fishing, mini spa, kayaking, KAYAKS (sit in/sit on) Kayak Lake Delton to Mirror Lake Continental breakfast.

Superhost

A large outdoor pool is surrounded by lounge chairs and shaded areas. The clear blue water reflects the sky, and the pool area is complemented by well-maintained landscaping. Nearby buildings with a relaxed architectural style provide a welcoming backdrop.

Villa in Lake Geneva

4.64 out of 5 average rating, 55 reviews

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!

Superhost

The image displays a clear outdoor pool area surrounded by a concrete deck. Two basketball hoops are positioned beside the water, and several lounge chairs are arranged along the perimeter. The multi-story building, featuring stone and stucco facades, provides a backdrop with greenery enhancing the environment.

Villa in Wisconsin Dells

New place to stay

Sunset Fairways - Accessible | Chula Vista Condo

Modern, ADA-accessible studio in Chula Vista Golf Villas! Enjoy 2 queen beds + pull-out, full kitchen, smart TV, and step-free access. Privately owned unit—purchase access to Chula Vista’s waterpark & golf separately. Peaceful location near downtown Wisconsin Dells, Mt. Olympus, and outdoor adventures. Ideal for family getaways or couples' retreats. New photos coming soon—book your stay today!

An outdoor patio space is illuminated by string lights against a twilight backdrop. A fire pit occupies the center, surrounded by four chairs. The wooden railing features horizontal slats, adding texture to the setting, while large windows of the house reflect the warm glow.

Villa in Lake Geneva

4.87 out of 5 average rating, 30 reviews

Secluded 3 br Villa Patio BBQ, EV-Charger! Sleeps9

Newly renovated in 2021. Located in a secluded area and surrounded by trees/woods. 5 min drive to Walmart, Target, HomeDepot, and Downtown Lake area. Close to many bars and wineries. 5min drive to Grand Geneva Ski and resort 20min drive to Alpine Valley and Wilmot Mountain Ski Resort Perfect place for great family time and lots of fun in a stylish atmosphere.

Guest favorite

Two-story condos are seen, featuring spacious balconies and large windows. The manicured lawn is well maintained, with a gentle slope leading up to the buildings. A few trees and clouds are visible in the background, creating a peaceful outdoor environment.

Villa in Deerfield

5 out of 5 average rating, 29 reviews

Beautiful 8Br/6Ba 20min - Alliant Energy Center

Exclusive Condos constructed with high end finishes and amenities next to woods, hiking/biking trails and near several lakes. Pricing is for both sides and 2 night minimum. You can book each side separately. Search YouTube Video: 217 Oak Savannah Walkthrough Deerfield Wisconsin & 221 Morningside Dr Deerfield Wisconsin 7/25/24