Villa holiday rentals in Madison

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Top-rated villa rentals in Madison

Guests agree: these villas are highly rated for location, cleanliness and more.

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Guest favourite
A log-sided home is illuminated by warm lights against a snowy landscape at night. The covered porch features railing and seating, with snow blanketing the ground and surrounding trees, creating a serene winter scene.
Villa in McHenry
4.91 out of 5 average rating, 35 reviews

Fabulous Cabin

WELCOME TO WATERFRONT LOG-SIDED HOME! ARTISAN CRAFTMANSHIP HOME OFFERS A BACKYARD OASIS SITUATED , NESTLED ON A PRIVATE POND, Heated POOL(closed till April 1st), Hot tub open from Oct 15th to Apr 15thGAZEBO, FIRE PIT, FISHING! 4 BEDROOMS AND 4.5 BATHS The homes sits on the highest point in the neighborhood and has stunning views in the front & backyard! Enjoy the mornings sitting on your front porch. The main floor is completed by an office, finished walkout basement in with a custom built bar

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, 70 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!

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, 8 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!

Guest favourite
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? Book early to avoid disappointments like 2025 we experienced. For her, specialty soap and lotion, complementary spa robe. Private property, wildlife decor, full kitchen, WiFi, fishing, breakfast items. kayaking, KAYAKS (sit in or on)

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
4.65 out of 5 average rating, 57 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!

Guest favourite
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!

Superhost
Villa in Fort Atkinson
5 out of 5 average rating, 5 reviews

King Suite W/ Hot Tub & 8-Jet Massage Shower

             THE ROUND MULTI COLOR RIVERBATH/WATERFALL HOT TUB SUITE     This Beautiful Luxurious Romantic Round Hot Tub Suite in Back and white imported Marble and 8-Jet massage Shower is avaiable Mostly for the Starlight Tower Manor Guests. but when the Manor is not rented then guests can rent the Love Hottub suite like a hotel room from monday thru thursday night/fri morning if the manor is not rented.

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, 145 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
Villa in Wisconsin Dells
New place to stay

Sunset Fairways - Accessible | no stairs.

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!

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 well-appointed indoor hot tub is centrally featured, surrounded by spacious living areas. Natural light fills the room through large windows. A comfortable seating area is visible in the background, and a TV is mounted on the wall opposite the hot tub.
Villa in Bellevue
4.97 out of 5 average rating, 77 reviews

Riverview Villa - Hot Tub Suite (River Rock Inn)

Explore the mighty Mississippi River in this newly renovated historic villa with enough room for the entire family! Enjoy panoramic views of the river from every window and relax in your well appointed outdoor space or indoor hot tub. Walk to downtown shops, restaurants and brewery!

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 BR Lock-off 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 £386 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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