Villa holiday 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, 62 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

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
4.87 out of 5 average rating, 69 reviews

Interlaken Villa: Steps to Lodge Geneva National!

The perfect retreat begins at this 1-bed, 1-bath vacation rental! Nestled steps away from the Lodge Geneva National- 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!

An outdoor patio area is presented, featuring a stone pathway leading to various seating arrangements, including white chairs. Decorative garden elements, such as a stone fountain and a small statue, enhance the inviting ambiance surrounding the mansion's exterior.
Private room in Columbus

Romantic 1854 Governor Mansion Main Bedrm dogs ok

Travel back in time to a Romantic 1850's mansion for meetings, weddings, photo shoots, private events. Romantic 1850's 4BR Mansion near Madison majestically sits on the highest point in Columbia County on nearly two acres of manicured landscape. Governor James T. Lewis, the ninth Governor of Wisconsin (1864-66), led the state through the tumultuous conclusion of the Civil War. The movie Public Enemies with Johnny Depp was filmed in this town. Feather top on some of the beds. Allergic? LMK

Guest favourite
A five-star illustration of the Original Tree Top Villa is depicted, surrounded by tall pine trees and reflecting on the still waters of a lake. The structure features multiple levels, each with balconies, enhancing the connection to nature.
Villa in Wisconsin Dells
4.95 out of 5 average rating, 39 reviews

Location,Location. On Lk Delton, near Devils Lake.

Private TREETOP ON LAKE DELTON, near DEVIL,S LAKE…..,5 Star! DEVIL’s LAKE, the busiest state park in Wisconsin is only 20 minutes away! The Dell View offers you the best… A day at Devils lake, nights on lake Delton. How about lunch in Baraboo? Mini SPA FOR HER spa products complementary.and mini SPA set up just for her, samples, robe, set up. Private property, wildlife decor, full kitchen, WiFi, fishing, mini spa, kayaking, KAYAKS (sit in or on) Continental ovati

Top guest favourite
The exterior of the Lodge is highlighted by a two-story structure featuring a white railing across the upper balcony, adorned with patriotic bunting and American flags. Comfortable seating is available on the porch, with stair access to the second floor.
Private room in Briggsville
4.95 out of 5 average rating, 145 reviews

The Lake Mason Lodge

Lake Mason Lodge - once an 8 unit motel has been re-imagined as large family or group lodge exclusively thru AirBnB. This “Lodge” theme allows families or large groups to gather in a common area inside or outside, to socialize on the full length upper/lower porch or around the fire-pit, gas grill gazebo or green space area, for relaxing and games. Bring your family and friends for a relaxing stay at The Lake Mason Lodge. *No pets allowed*

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, 56 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
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
4.84 out of 5 average rating, 38 reviews

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!

Guest favourite
An aerial view of the living room is displayed, showcasing a dark leather sectional couch positioned around a textured area rug. A wooden coffee table is centered in the space, while a flat-screen television is positioned next to a large stone feature wall. Natural light fills the room through large windows.
Villa in The Galena Territory
4.88 out of 5 average rating, 137 reviews

Spring Creek Sanctuary-2BR-Owners’ Club Access

Welcome to Spring Creek Sanctuary! This 2BR/2BA condo in Galena Territory offers comfort and nature. Relax by the wood-burning fireplace, cook in the modern kitchen, or unwind on the private deck with wooded views. Enjoy Owners’ Club amenities—pools, fitness, game room, tennis—plus nearby golf, trails, and Lake Galena. Just 15 minutes to historic downtown Galena, shopping, dining, and wineries!

Superhost
The exterior of a modern multi-story building is captured under a clear blue sky. The structure features a mix of wood and stone accents, along with large windows. A parking area in front is visible, highlighting a white vehicle and neatly arranged landscaping.
Villa in Wisconsin Dells
4.56 out of 5 average rating, 9 reviews

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!

Superhost
A welcoming exterior view of a two-story condo is surrounded by lush green foliage. A pathway leads to the front porch, which features a post lamp. The home is shaded by trees, providing a natural backdrop and a sense of tranquility.
Villa in The Galena Territory
4.75 out of 5 average rating, 60 reviews

Galena Territory 2BR Condo | Semi-Private Pool

Enjoy nature’s splendor (and a semi-private pool!) at Walnut Hill Hide-a-way, a cozy 2BR/2BA condo in the Galena Territory. Relax in the living room with fireplace, cook in the well-stocked kitchen, or unwind on the deck with wooded views. Perfect for families or small groups, with pool access just a 1–2 minute walk and other Territory amenities to enjoy during your stay!

Guest favourite
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, 30 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

Guest favourite
A stone entrance gate with a tower stands at the beginning of a well-maintained road. Lush green trees line both sides of the driveway, providing a natural frame for the welcoming entryway to the resort.
Villa in Lake Geneva
4.9 out of 5 average rating, 80 reviews

2 Bedroom Villa at Lake Geneva's GRAND Resort

Enjoy a spacious, two-bedroom lock-off villa that sleeps up to 8 adults at the AAA 4-Diamond GRAND GENEVA RESORT, voted one of the top resorts in the Midwest by Condé Nast Traveler. Comfortable accommodations and countless resort amenities make for a fun and relaxing getaway.

Popular amenities for villa rentals in Madison

Quick stats about villa rentals in Madison

  • Nightly prices starting at

    Madison holiday rentals start at £395 per night before taxes and fees

  • Verified guest reviews

    Over 20 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Madison rentals

  • 5 Average rating

    Madison stays are highly rated by guests – averaging 5 out of 5!

  • Nearby attractions

    Madison’s top spots include Henry Vilas Zoo, Wisconsin State Capitol and Olbrich Botanical Gardens

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