Family-friendly holiday rentals in Jeffersontown

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.

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.

"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!!

The Pearl Airstream at Progress in Derby City

Meet our Pearl Airstream. She's a 1989 Squarestream. That's right, a SQUARE Airstream! There were less than 300 made from 1989-1991, so this is your chance to stay in one of very few in existence! She sleeps 4, possibly 5 depending on your comfort level. There's a private bath/shower. You'll have a kitchen & covered patio with grill & firepit. There are 11 total units on site. 2 houses, 8 airstreams & a bunk house. *DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

4th Street Suites - Stunning 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!

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.

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.

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!