Family-friendly vacation rentals in Middletown

4.86 out of 5 average rating, 190 reviews

Guest suite in Prospect

Private Entry, full suite w/game rm. Kitchenette.

Golf course community, walkout basement with private entry. Flat screen TV, WiFi, Private Bedroom. Large Family rm with pull out Queen sleeper sofa, pool table, Hardwood floors. Refrigerator, microwave and coffee maker, Keurig. Toaster/hot plate and basic dishes/ cooking utensils are included. (one review stated dishes weren't clean) I was trying the whole open shelf look and didn't realize I would need to clean the dishes more often since they weren't in a cabinet) Private patio. Large yard.

4.95 out of 5 average rating, 345 reviews

Cabin in Louisville

Captain's Cabin: Bourbon Trail, History & Romance

Your own log cabin on a wooded hillside with gourmet breakfast served to your door (on weekends)! It's been the location for 5 movies, including Lifetime! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife by the lake, creek or from back porch swings. Comfy bed, luxury sheets, high-speed internet, bluetooth stereo and special touches make your stay magical! Ask for Cooking With Bourbon Experience.

Guest suite in Louisville

4.94 out of 5 average rating, 288 reviews

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.

5 out of 5 average rating, 235 reviews

Cabin in Louisville

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.

5 out of 5 average rating, 233 reviews

Perfect for Work or Play, Close to Everything!

Whether you're here for work or play, our Airbnb offers the perfect base for your Kentucky adventures! Welcome to your home away from home! Nestled in the quiet suburbs, our modern & spacious retreat offers the perfect blend of comfort & convenience. Whether you’re here to explore the famous Bourbon Trail, work remotely, or simply unwind, you’ll find everything you need right here! Close to shopping, dining, entertainment, major highways, top bourbon distilleries and downtown Louisville.

4.87 out of 5 average rating, 215 reviews

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.

Guest suite in Louisville

4.95 out of 5 average rating, 158 reviews

Derby City Hideaway

Whiskey Hollow offers you a unique stay with our Bourbon-themed space. Your stay in Kentucky is sure to be memorable and cozy. Our guest suite offers a full kitchen, cozy living area, bedroom and full bath with a private patio. Local attractions include Churchill Downs, home of the Kentucky Derby, Kentucky Derby Museum. Louisville Slugger Museum, Kentucky Bourbon Trail, local city eats, 4th Street Live, horse farms, hiking, waterfalls, parks, shopping, local arts, and much more!

4.95 out of 5 average rating, 147 reviews

Camper/RV in Louisville

The Dotti Airstream @ Progress Park in Derby City

Glamping at its best in our 1964 Airstream Bambi named "Dotti". Dotti is 16ft long and can sleep 2 adults. Enjoy vintage glamping in the most serene setting. Step out to coffee in the hammock, or go on a morning kayak ride. Dotti is our smallest offering, but has TONS of charm. Including a large covered patio with a swing bed! Please note Dotti does not have hot water. Progress Park Airstream resort has 11 total units on site. 2 houses, 8 airstreams & a bunk house.

Condo in East Market District

4.92 out of 5 average rating, 147 reviews

Perfect Nulu Getaway w/ Best Location- low fees

You can’t find a better location in the city. Welcome to Lou Lou on Washington, our Nulu condo. We are located just steps away from the best food, drinks, and events in the derby city. We are located on a quiet street, only one block away from Main St. You can walk to breweries next door or even a soccer game at Lynn Family Stadium. The Yum Center is only a few blocks away, and we have one of the few properties located walking distance from Waterfront Park.

4.93 out of 5 average rating, 146 reviews

HOUSE ON HERRICK

Fully renovated home in the heart of Historic Middletown. Hardwood and tile floors throughout. Queen size memory foam mattresses in both bedrooms and a full-size blowup mattress can be used in the living room if needed. 3 blocks from Main Street where you will find restaurants, shopping, and antiques! 15 minutes from Churchill Downs! Less than 1 mile to Interstate 64 with a quick Uber ride to downtown, Crescent Hill, and the Highlands.

4.97 out of 5 average rating, 173 reviews

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.