Holiday rentals with outdoor seating in Jefferson County

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.

Walking Bridge, Putt Putt House

NEW LISTING: Welcome to our walking bridge home on Pearl St. We have a hot tub, putt putt, and all the fun you can think of in one home. Steps away from restaurants, shopping, and bars, as well as the walking bridge to Louisville. This home is closer to the fun in Louisville than most neighborhoods in Louisville itself. Go out or stay in, you're guaranteed to have a great time in this newly renovated gem. We have high quality mattresses, and smart TV's in both bedrooms and the living room.

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.

Lilly's Pad

Relax and unwind in between all your Louisville activities. We are close (4.4miles) from SDF airport ,and I65 and the Gene Snyder Freeway are less than 8miles away. There are a plethora of activities from shopping to entertainment venues such as horse racing at historic Churchill Downs, Louisville Zoo, Kentucky Kingdom amusement park, Muhammad Ali museum and childhood home, Louisville Slugger Museum, Valhalla golf club, and 36 Bourbon Distilleries as well as cave exploring and fishing.

Beachfront River Cottage

Escape to our Beachfront River Cottage for tranquility and breathtaking panoramic views of the Ohio River. Whether you're here for the Kentucky Derby, Music Festivals or a quiet weekend away, this charming retreat offers the rare luxury of a private beach and modern comforts. Featuring a glass-enclosed, AC/Heated porch—perfect for morning coffee or sunset dinners year-round. Equipped with a full-size gas grill, Adirondack chairs, a picnic table, and a fire pit for cozy evenings.

The Writer’s Den

Take it easy at this unique and tranquil cabin getaway. Nestled on a wooded hillside overlooking the Louisville skyline, The Writer’s Den is a great place to call home. Located just off interstate 64 and 10 minutes from downtown Louisville, the cabin gives peaceful seclusion and location convenience for those looking to explore the area. With a screened in porch, back deck lounge, loft space and all the comfort amenities, you’ll be on your way to writing the next great novel!

Highlands Carriage House

Secluded Retreat in the Heart of the Highlands! Perfect for DERBY! Our carriage house is perfectly located in the heart of all Louisville has to offer. We are only steps from the finest dining, entertainment, pubs, shopping, parks, and coffee in Louisville. Bustling and eccentric Bardstown Road is only half a block away, yet the Carriage House feels secluded and very private. It is located 5 miles from Churchill Downs, 7 miles from the airport, and 2 miles from downtown.

Sleek urban condo near Kentucky Bourbon Trail

Discover the perfect blend of comfort and culture at Urban Bourbon Escape, a stylish and modern condo located in the vibrant heart of Louisville. Whether you're sipping your way through the Bourbon Trail or exploring the city’s historic charm, this sleek retreat is your home base for all things Louisville. Enjoy city views, walkable access to top attractions, a fully equipped kitchen, and a cozy space designed for couples or small groups to relax and recharge.

The Green House in Downtown

Newly renovated 1920s shotgun house in Downtown New albany. Perfect for those who want the convenience of being in the middle of it all, but still want an authentic and stylish oasis to relax in. Comes with all the amenities you would expect for a convenient stay including fully equipped kitchen, private back yard, off street parking, and self check-in. Walk or Bike your way to many local restaurants, shops, or take the byway to enjoy the scenic Ohio River.

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.

Derby City Bourbon Bungalow - by Germantown & UofL

This charming bungalow is fully renovated and well appointed for guests. It's conveniently located near all of the hot spots in Louisville. We are just minutes from Churchill Downs, Germantown, NuLu, Louisville Airport, the Yum! Center, Slugger Museum and Waterfront Park. There are countless restaurants, parks, shops and bars nearby. Relax and enjoy the many amenities in and around our home. We have 3 bedrooms and 2 full bathrooms.

The Caldwell Highlands/Germantown

Welcome to The Caldwell, a Germantown/Highland area home that includes three bedrooms, one and half bathrooms and sleeps up to five people. The home is within walking distance of several restaurants, bars, retail and vintage stores, and entertainment venues including the Germantown Gables, Logan Street Market and Old Forester’s Paristown Hall. The home features a covered deck, a fenced-in yard as well as home gym.