Holiday rentals in Windy Hills

RIView 103. Modern Waterfront Suite Kentucky Derby

Guests can enjoy scenic views of the mighty Ohio River from any room in their private suite. Catch a beautiful sunrise or relax while sitting on the porch watching the boats and barges cruise the river. Close drive to interstate to get you to downtown Louisville to enjoy a dinner, museum, basketball game or concert in the KFC YUM Center and the world famous Churchill Downs! 1 mile away from River Ridge. We do offer a Tesla only charger or you can bring your own standard attachment for a charge.

Swanky Fully Equipped St. Matthews Apartment

Swanky East End Private Apartment. Completely renovated in 2018. New Shower, fully equipped kitchen. Huge walk in closest, FlatScreen TV and WIFI all included. Party Deck and Spaceous Living Room are ready for your Visit. King Bed and Queen Sleeper Sofa with spacious living, await up to 4 guests. Great venue for Trinity Football, University of Louisville Sporting events, Churchill Downs, or simply hitting the Bourbon Trail. 10 min. Uber to Whiskey Row and Distillery And/or and Nulu District

Hide away close to everything

Recently remodeled in law suite. We just upgraded the bed to a queen size. Very private, detached garage getaway. A cozy sitting area 60" CableTV with HBO SHOWTIME and STARZ. Wet bar with fridge, ice maker, coffee maker, microwave, hot plate, dishes and some cookware. Private bath has shower and a walk in closet. This private apt. is above the garage. Outside has fenced in yard for your furry friend, outdoor fire pit and sitting area. Close to the interstate and minutes from downtown.

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

Exclusive two-story retreat close to attractions!

Discover this inviting two-story apartment located in the heart of Louisville. Perfect for families or small groups, this thoughtfully equipped home comfortably sleeps up to 7 guests with two queen beds and a sofa bed. Enjoy the convenience of a fully equipped kitchen, flat-screen TVs, and reliable high-speed WiFi. With comfortable living spaces, dedicated parking, and proximity to local attractions, this charming retreat offers an ideal blend of comfort and convenience for your next stay.

The River's Edge Oasis, close to downtown

Welcome to your oasis on the water! Relax and unwind at the River's Edge. This home is about as close as you can get to paradise in Louisville Ky (also known as River City)! Perfect getaway for a romantic weekend or the best place to relax after a long day of work! Voted #1 Vacation rental in KY by Dreamy Stays!! This unique home is designer decorated and updated with all the amenities! An 8 minute drive to downtown Louisville, the oasis offers the best of both worlds. Book today!

Quiet Neighborhood Home With Outstanding Location

Situated on a quiet hilltop neighborhood in Clifton Heights, this is the perfect location for a professional or personal visit to Louisville and very animal friendly. It is within 10 minutes of Downtown, Waterfront Park, Nulu, Frankfort Avenue, the Highlands, the Convention Center, and just 15 minutes from historic Churchill Downs. These neighborhoods feature the best dining and entertainment in the city. Just a block away is the Mellwood Arts Center complex with shops and dining.

Olive Branch Suite with projector screen in E Lou

This suite is a beautiful private retreat complete with a projector for watching your favorite streaming service for the ultimate movie night. Centrally located and within 10-20 minutes of numerous local hospitals, universities, as well as various restaurants and downtown destinations, our guest suite offers a peaceful retreat in a convenient and safe location. We also provide a fold out desk that guests can use for a remote work space if desired.

My Old Kentucky Dome

An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.

...Happy Trails House in Derby City

4 bedroom, 2 full baths, 1 half bath, ( bedrooms on 2nd floor, none on 1st floor ). Our home is on a dead end street steps away to a walking trail, fenced yard, 2 patios, charcoal grill. Only 15 to 20 min. drive to Downtown, Churchill Downs, Hospitals, Airport, close to major highways. Near restaurants, shopping centers, grocery, liquor store etc. pets welcome with $10 fee per pet per night. Washer/dryer and dishwasher

Hidden GEM, newly furnished in a safe, great area

Our “unit” is a great place to stay. Absolutely wonderful neighborhood with beautiful historic setting, cozy, safe and quiet. Short walking distance to many restaurants, shops, coffee houses. Majestic trees line properties and homes. Downtown & NULU 4 miles. Churchill Downs 10 miles, University of Louisville is 13 miles away. Golf & swim center .25 miles this. property is duplex. Very separate accommodations! Private!

The GiGi Airstream, Lakeside at Progress Park

Your stay in the Gigi Airstream at Progress Park will be anything but ordinary. Wake up to stunning views of the water, with the beach sand just outside your door. This 2022 Airstream Flying Cloud has all the bells and whistles and will ensure you are not roughing it while glamping in the city limits! We can't wait to host you! *DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.