Pet-friendly holiday rentals in Jeffersonville

Cozy cottage, pets, private, convenient, parking

This secluded mid century cottage is just minutes to downtown and other amenities. Located in Clifton Heights, this three bedroom, bath and a half home is inviting and cozy. Located 6 miles from two large malls, 1 mile from the new walking bridge over the Ohio River, and one and a half miles to unique shopping, nightlife and restaurants. Also, the home is only a short distance to I 71 and I 64. This makes everything convenient and accessible from this private location. The home has vintage charm with renovations for convenience. Each Bedroom has a flatscreen TV as well as a 56 inch flatscreen in the living room. There is a private front yard with gardens, seating, and a grill. There are 6-7 spaces for off street parking. The eat-in kitchen seats six, with a double oven microwave, full-size fridge, gas stove and a dishwasher. There is service for 12 including Louisville Hadley Pottery.

BRAND NEW, Jeff, IN Cottage, The Newport

Welcome home to this cozy family retreat. Enjoy this private 4 bedroom/2 bath home LESS than 10 minus to all the best things to do in Southern Indiana and Louisville! LESS than 15 mins to KY Expo Center and Churchill Downs. Less than 30 minutes to Huber's. Gather in the living room to play games, watch TV or cook in the fully equipped kitchen. Enjoy all of the local distilleries, or one of the many museums, catch a soccer or baseball game then grab a bite to eat in Jeffersonville or Louisville.

Derby Ready! With comfortable beds and Hot Tub!

Come enjoy our fun house , we have a hot tub, fire pit and fully fenced private outdoor area , that makes for perfect day in or nights with our string lights and cozy fire pit! We’re only 2 miles from the hustle and bustle of downtown Jeffersonville and 4 miles across the bridge to Louisville’s downtown area. We have top of the line comfortable mattresses and cozy bedding! Fully fenced in backyard and Pet Friendly with a Fee, stay in or go out, either way you’ll have a great with ample space.

Kentucky Hug: A Modern Shotgun for Bourbon Elites

A “Kentucky Hug” is the warm feeling one gets after sipping whiskey. Get that feeling at this renovated shotgun home in centrally and conveniently-located Irish Hill! One block away from Baxter Ave-- the original Highlands! One mile to a few urban bourbon distilleries. A quick Lyft to NULU, Butchertown, Clifton, the convention center, and KFC Yum Center. Easy access to I-64, I-65, and I-71. Walking distance to Headliners Music Hall, Gravely Brewing, and other great eats. Permit No: STR926031

Walking Bridge, Putt Putt House

NEW LISTING: Welcome to our walking bridge home on Pearl St. We have a hot tub, putt putt, and all the fun you can think of in one home. Steps away from restaurants, shopping, and bars, as well as the walking bridge to Louisville. This home is closer to the fun in Louisville than most neighborhoods in Louisville itself. Go out or stay in, you're guaranteed to have a great time in this newly renovated gem. We have high quality mattresses, and smart TV's in both bedrooms and the living room.

The Sweet Spot! - Live Like a Local

Live like a local in one of Louisville’s most sought-after neighborhoods, young professionals and families alike. Rich in history and surrounded by wall-to-wall dining, shopping, and entertainment, this vibrant area is known for its charm, energy, and premium appeal. Originally built as a single condo over two decades ago, the owner later acquired the neighboring unit and completely reimagined the entire second level. The result is a thoughtfully crafted space that truly feels like a retreat.

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.

Upscale Riverfront Home,HotTub,FirePit,Sauna,Views

Luxury riverfront retreat on the Bourbon Trail, just 15 minutes from Churchill Downs and minutes to downtown Louisville. This private, pet-friendly home sleeps 12 and features a hot tub, sauna, home theater and game room—perfect for Derby stays, distillery tours and group getaways. Unwind by the fire pit with stunning Ohio River views or relax on the expansive deck. An upscale Kentucky escape designed for unforgettable stays. Discounted Derby 2026 dates available.

Firepit/Gaming/Historical bldg.

Only a 1 min drive to the revitalized heart of New Albany and short 7 minute drive to downtown Louisville. This stylish 2 br 1 1/2 ba loft like flat was a grocery in the early 1900s. It was renovated to bring back the exposed brick wall, beams and knotty wood floors. The-remodeled bathroom has a new soaking tub and stand in shower. The middle BR also has a futon that pulls out to sleep 2 more. There is also an outdoor firepit on a paved area.

The Caldwell Highlands/Germantown

Welcome to The Caldwell, a Germantown/Highland area home that includes three bedrooms, one and half bathrooms and sleeps up to five people. The home is within walking distance of several restaurants, bars, retail and vintage stores, and entertainment venues including the Germantown Gables, Logan Street Market and Old Forester’s Paristown Hall. The home features a covered deck, a fenced-in yard as well as home gym.

Charming Home minutes from Louisville

Your family will enjoy this centrally located 2 bedroom 1 bath modern home that’s walking distance from downtown New Albany and 13min drive from downtown Louisville. With walking paths, small shops, and a sweet bakery just around the corner, your family can explore our little town. Located on a quiet street and surrounded by historic New Albany, you can end the night on our covered fenced in patio.

HIghlands Modern Get Away

Ideal, quiet place in the highlands. You have the apartment over the garage. You'll have a place all to yourself with most the amenities of your own home. Studio apartment with a balcony if you decide to hang out and relax for the evening. There is a cook top, but no oven in the kitchen. Park in the driveway in front of the garage. Pets are welcome, plz add them when booking.