Holiday rentals with outdoor seating in Middletown

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.

"Call Me Old-Fashioned" in Derby & Bourbon Country

Welcome to "Call Me Old-Fashioned" - a unique spin on Bourbon w/ a mix of new & vintage amenities! Located in a QUIET & SAFE neighborhood, this family-friendly home is located close to Downtown Louisville & Churchill Downs (18 min), Expo Center & airport (15 min). Bardstown, the Bourbon capitol, is 35 min away. We are also 5 min from Parklands @ Floyds Fork park system - home to 60 miles of hiking, biking & paddling trails & a big playground. Come make yourself at home in our cozy KY home.

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.

Cheerful, centrally located 2 bedroom shotgun home

This welcoming home is central to Louisville's most popular and lively neighborhoods, walking distance to many favorite spots. Natural light and unique art fill the home. There is a large deck that overlooks a beautiful cemetery behind the home, and is a perfect place enjoy morning coffee or sunset dinner. A coffee/tea bar is located in the fully equipped kitchen. Charging stations and white noise machines are found in both bedrooms. 2 workstations and a smart TV are also available.

Private EAST END gem, minutes to everything!

Cozy, East End cottage just minutes from Top Golf, shopping malls, restaurants, entertainment, and other amenities. Easy access to the expressway. Home is well appointed with granite countertops, stainless appliances, hardwood floors, and more. A seasonal creek across from the house can be heard giving the impression of a cabin in the woods with privacy and seclusion, with the convenience of city living at your fingertips. There is also a beautiful park steps away from the house.

Lumos Stays: 65" 4K TV, memory foam, kid-friendly

Michael and Ashley (Lumos Stays) welcome you to Louisville, home of bourbon! Centrally located, minutes from the interstate, and close to downtown and the bourbon trail, this is your home base for adventure. Enjoy the 65" 4K Roku TV, fast wifi (~317mbps), green tea memory foam mattresses, modern kitchen, kid-friendly amenities… and did you see that outdoor space? Solo Stove fire pit, hammock, propane grill, and games. Enjoy the private fenced-in backyard and large driveway!

Private Prospect Flat

Two bedroom apartment located on picturesque Covered Bridge Road in Prospect, KY. There is a separate entrance with plenty of parking. Beautiful views of Kentucky landscape from every window. Our property is four acres with a meandering stream, forest, and fields. There is a fully stocked kitchen including a dishwasher. The main bedroom includes a work space area and two closets. Feel free to grab a few eggs for breakfast if there are eggs in the nesting boxes.

The City Cottage…quiet, peaceful, and convenient!

A quaint, cozy, and private space close to everything Louisville has to offer. Located on the Northeast side of Louisville, The City Cottage is near the highways for quick access to destinations in and around Louisville. This newly completed space is fresh, clean and created for guests in mind. Are you a couple traveling or a business person wanting more room and comfort than a typical hotel? The City Cottage is for you! (Three night minimum during Derby time.)

Quaint Highland's Bungalow

Kick back and relax in this calm, stylish space with equal proximity to beautiful Cherokee Park and all the shops and restaurants on Bardstown Road in the popular Highland's neighborhood. Two bedroom, one and a half bath, completely updated one hundred-year-old home. The backyard offers a beautiful firepit with Adirondack chairs, a patio with dining area and Traeger Grill and plenty of room in the landscaped backyard to throw a ball. Three day minimum stay.

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.

Newly Updated: Spacious Suite/Private Entry

My guest suite is close to restaurants, business parks, shopping and easy access to highways. Guests love this place because of the big trees, green space and private entrance. The patio is great for sipping morning coffee, reading or enjoying an evening beverage. Beautiful, quiet neighborhood is perfect for a walk/run. This spacious, comfortable suite is good for couples, solo adventurers, business travelers and small families.

"The Brook" - Louisville

Enjoy a stay at this spacious, beautifully decorated ranch home in East Louisville. Blending organic modern decor and intentional functionality, you will feel relaxed and right at home. The home is nestled in a quiet neighborhood and yet only 1 mile from the interstate - conveniently located, a drive anywhere isn't far. Bring your crew to town to experience a day at the horse track, a bourbon tour, or a Kentucky family getaway!