Holiday rentals with outdoor seating in St. Matthews

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.

4th Street Suites - Serene King Bed Suite

Live the best of Louisville in this sleek 1‑bed, 1‑bath downtown retreat! Perfect for couples, families, or friends, it features a cozy king bed, 2 rollaways, a fully stocked kitchen, and a bright living area. Enjoy morning coffee or evening drinks on your private balcony, stroll to nearby restaurants and bars, then relax by the pool or hot tub, play a round in the golf simulator, or unwind with a game of pool. Your launchpad for adventure—or a quiet, stylish escape when it’s time to rest!

3 bedroom Crescent Hill cottage

Located on a wide, tree-lined avenue, this comfortable, stylish, and well-appointed Dutch Colonial is only a few minutes drive from Louisville's most popular entertainment districts, restaurants, and boutique shops along Frankfort Ave, Bardstown Rd, NULU and Downtown. Guests will enjoy the surroundings of one of Louisville's most desirable neighborhoods with Whitehall and Boyce College within walking distance and Garden Court, as well as historic Cherokee Park just a short drive away!

Fall Haven - King Beds, Hot Tub

* 3 Bedrooms, 5 Beds, 2 Living Rooms. * 2 1/2 Baths * 2,500 sq ft (235sqm) * Private patio * (2) 60” Smart TV's w/Bluetooth speaker * Attached garage * Fully equipped Kitchen, upgraded appliances & sink * Flat screen TV in each bedroom & cable * Safe neighborhood * Close to local spots shopping malls in Louisville, gym, and St. Matthews *Kentucky Derby, Bourbon and Beyond and Louder than Life guests inquire first. A strict cancellation policy is required*

Eclectic/Modern 1 BR in Clifton!

Updated 1 bedroom/1 bathroom stylish retreat right in the heart of the Historic Clifton neighborhood. Clifton is directly off Frankfort Avenue near the Highlands, Nulu, St Mathews, and Old Louisville neighborhoods. This 600 sq ft charming shotgun home was built in the 1900’s and it has a ton of character and “old home” charm, while still having updated features throughout. This home is very close to many restaurants and shops! You can walk, drive, or bike to Frankfort Ave.

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.)

*Walk to Churchill Downs!*Close to Expo, UL, YUM!

This house just went under a full renovation! Everything is new and awaits your stay. This property is only .4 miles away from the historic Churchill Downs! A quick Uber or cab ride will get you to 4th Street Live, the Highlands, Frankfort Ave, and many more attractions. We are also only 1.9 miles away from the Kentucky Fair and Expo Center which hosts events every week, concerts, Kentucky Kingdom amusement park, and the state fair.

"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!

One Room Apartment with Private Off Street Parking

Room is a stand alone efficiency with a kitchenette, blackout curtains, and reclining queen bed. It has one designated parking space and seperate entrance. Unit has private bath and walk in closet, and kitchenete. Also has refeigerator, coffee maker, work desk microwave, 42" smart tv, Ninja airfryer oven, and couch. Private porch with table and chairs. Close/secure single parking space.