Family-friendly holiday rentals in Middletown

5 bedroom/4 bath Walk to All, Historic Highlands

4 traditional bedrooms (5th convertible den/bedroom), 4 bath with great deck, porch and patio. 2 king bedrooms, 2 queen bedrooms, 1 queen sleeper and den double sleeper. Fabulous 3rd floor primary suite, updated baths, stylish mod kitchen. Beautifully remodeled 2500 sq. ft. house in Cherokee Triangle, walk to everything- restaurants, parks, cafes, shops! Just 1/2 block off Bardstown Road and 1 block from Cherokee Park. Walk to dozens of restaurants, shops, café, theatres and two great parks.

Close to Louisville~Hot Tub~Fire Pit~Game Room

Welcome to Stone Creek, a private 3 acre estate conveniently located minutes to Louisville, KY. This is the Ultimate Getaway! Upon entering the premises, you will find a custom iron security gate requiring coded access. Stone Creek boasts 2500+ sq ft of luxury living space complete with a full kitchen, laundry, and office. Guests will have full use of the grounds including the hot tub, fire pit, and the numerous covered decks & patios. Perfect romantic getaway or multi person retreat.

Best view of the lake two bed two bath cottage #4

Make yourself at home in this cozy 2 bedroom 2 bath lakeside cottage with incredible views of Taylorsville Lake. You will love the open airy feel complete with deck and hot tub. Washer dryer, four beds that easily sleeps 7. TV in both the master bedroom and the living room. The wonderful community also offers a swimming pool and play area for kids. Enjoy the wildlife as well including deer and turkey as you explore the walking trails. We are located in the heart of the bourbon country!

Cabin on Lake Close to Louisville Ky

Welcome to Little Cedar Lodge, our little slice of heaven near the town of Elizabeth, Indiana. Enjoy the peace and solitude overlooking the quiet private lake (wake speed only), yet close to Caesar’s Casino, golf, wineries, and the city of Louisville with all its activities and nightlife. Great for a romantic getaway for two, or for your entire family. It would also be great for a small church or business retreat. We can accommodate up to 10 if you double up in some beds.

KY Derby 50% off - Lake View

Nestled in the Bourbon Trail hills of Kentucky, rests Taylorsville Lakes only waterfront vacation community. Strategically placed; Cottage 37 sits on a ridge that overlooks the 3,050-acre lake and its 10,000 acres of wildlife preserve. The owners tried to capture the view from the kitchen table to inspire the cabins four-season theme. The wall hangings were chosen to mirror Kentucky’s beautiful hills, Derby culture, and the water of Taylorsville Lake.

Charming Bourbon Bungalow - 1 Mile from Downtown!

You will love this quaint Germantown house located 2 miles from almost anywhere you would want to be in the city! Two bedrooms and one bath await you, along with a full kitchen, large living space, and spacious back yard. Close to many great restaurants, downtown attractions, the Highlands, Churchill Downs, the riverfront, and many great parks. Don't wait--book now!

Charming Shotgun Style Home, Great Location

This updated shotgun house is thoughtfully decorated with hints of handcrafted detail. Outdoor spaces include a front porch and a private patio. Cozy with a modern vibe. It can sleep up to 6. An ideal choice for couples, families, or a getaway with friends. Perfect for The Kentucky Derby and all Louisville has to offer.

Barret House, prime location, walk to everything!

Fully furnished luxury duplex, 3 bedrooms (recently added king, and also two queen beds) and 2 full baths, 2 chefs kitchens, with hide-a-bed and futon in second floor common area; This rehab has been designer decorated with a huge living area, it close to some of the finest restaurants in town. *No locals, please*

Southern Comfort-Hottub wlk 2 Resturant Row & Shop

Experience a truly distinctive home filled with character, personality, and endless fun! Enjoy the brand new Keurig/coffee maker combo. The trendy neighborhood boasts many bars and restaurants, making it a perfect base for hanging out with your group. Unwind on cozy beds for a restful sleep amidst the excitement!