Vacation rentals in Windy Hills

4.94 out of 5 average rating, 108 reviews

A circular fire pit area is surrounded by six dark wood chairs, positioned on a gravel surface. The space is framed by trees with autumn foliage, allowing natural light to filter through, creating a serene outdoor ambiance.

Villa in Prospect

Bourbon Trail, Firepit

After a beautiful drive along a tree-lined-canopied road, you will find Mint Julep Villa, located on a private 1.3 acre lot and just one street over from the Ohio River. Mint Julep Villa, is tastefully decorated for you and your family to enjoy your stay in the Louisville and Prospect KY area. No matter if it's the Bourbon trails, the Kentucky Derby, the numerous concerts and the many other attractions to draw you to Kentucky, Mint Julep Villa will be a place you'd be attracted to as well.

Guest suite in Louisville

An inviting outdoor space features a stone fire pit surrounded by several colorful seating options. Various patterned chairs and stools are arranged on a stone patio, with greenery providing a natural backdrop. A wooden table adds to the cozy ambiance of this fenced-in yard.

4.94 out of 5 average rating, 278 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, 214 reviews

The exterior of the stone cabin is framed by lush greenery and flowering plants. Sunlight casts soft shadows across the textured stone walls. A decorative statue stands on a pedestal near the entrance, complementing the natural surroundings.

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, 129 reviews

The Gladys Airstream is showcased under a covered patio, featuring wooden support beams and string lights. Outdoor seating includes a picnic table and multiple chairs arranged around a fire pit. The surrounding area is landscaped with gravel and green grass.

Camper/RV in Louisville

The Gladys Airstream at Progress Park - Derby City

This is our Gladys Airstream! She is a 2011 International Serenity. She sleeps 4 adults comfortably possibly 5 depending on your comfort level. Theres a queen bed in back, dinette folds to a double and the couch to a F/Q. You'll have a private bath w/shower & a kitchen. You'll also have a covered patio with your own private firepit and grill. Progress Park has a total of 11 units ( 2 houses, 8 airstreams & a bunk house). *DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

A spacious deck features a wooden surface with a set of six outdoor chairs and a matching table, providing an inviting area for gatherings. Large sliding doors lead into the interior, and greenery is visible beyond the railing.

4.92 out of 5 average rating, 265 reviews

Quiet Neighborhood Home With Outstanding Location

Situated on a quiet hilltop neighborhood in Clifton Heights, this is the perfect location for a professional or personal visit to Louisville and very animal friendly. It is within 10 minutes of Downtown, Waterfront Park, Nulu, Frankfort Avenue, the Highlands, the Convention Center, and just 15 minutes from historic Churchill Downs. These neighborhoods feature the best dining and entertainment in the city. Just a block away is the Mellwood Arts Center complex with shops and dining.

A wooden bridge extends over a lush green path, surrounded by vibrant trees and dense foliage. Sunlight filters through the leaves, creating a serene atmosphere. The bridge features metal railings, adding a modern touch to the tranquil natural setting.

4.99 out of 5 average rating, 250 reviews

NEW Hot Tub, Walk 2 Park, Whole Foods, Movies Mall

* 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*

4.96 out of 5 average rating, 232 reviews

A front garden displays vibrant orange flowers alongside lush green foliage. A yellow sign with red text is positioned among the blooms, while the steps leading to the entrance of the home are framed by stone edging. The entrance door is partially visible in the background.

Guesthouse in Germantown

Comfortable-relaxed space to find your inspiration

Located in the Germantown neighborhood of Louisville, this peaceful efficiency apartment in a traditional "shotgun" home, built in the 1890s, is within 10 minutes of nearly all of Louisville’s airport traveler’s attractions. Guests enjoy great sleep on top bedding and attention to detail. Sit on the front porch and let time slip by or spend the evening with a relaxing drink or meal in one of the neighborhood’s hip local eateries and bars. Plan your next journey.

4.96 out of 5 average rating, 303 reviews

Apartment in Louisville

Seneca View

Open, airy space with modern amenities. Plz, NO smoking, toking , vaping, or any drug use in/on property-- $300 fine. Convenient location in a quiet, sought-after neighborhood, yet within a few minutes of a bustling, busy Bardstown Road with lots of places to eat, shop and browse. Easy access from all major interstates: I-71, I-65 and I-64. Come stay for a week on business (work desk is set up) or use for a fun, getaway weekend.

4.85 out of 5 average rating, 255 reviews

A wooden deck features a circular table surrounded by four black metal chairs. The space is enclosed by wooden railing and overlooks a neighborhood scene, showcasing greenery and nearby structures under a partly cloudy sky.

Apartment in Butchertown

The Point at Story and Frankfort Avenue

The Point is a spacious and completely renovated one bedroom (king) apartment. You will absolutely love the huge sectional couch while watching your favorite shows on the 65" smart TV. Unit very close to downtown with tons of options for local restaurants, breweries, bourbon tours and bars. Building is located in the heart of Butchertown right down the street from the new Botanical gardens, Nulu, walking bridge and soccer stadium.

4.96 out of 5 average rating, 142 reviews

The exterior of a historic home features intricate architectural details with tall windows and a central tower. Surrounding the property are well-maintained gardens and mature trees, contributing to a serene setting. A spacious porch is visible, providing access to the main entrance.

Condo in Crescent Hill

Hidden GEM, newly furnished in a safe, great area

Our “unit” is a great place to stay. Absolutely wonderful neighborhood with beautiful historic setting, cozy, safe and quiet. Short walking distance to many restaurants, shops, coffee houses. Majestic trees line properties and homes. Downtown & NULU 4 miles. Churchill Downs 10 miles, University of Louisville is 13 miles away. Golf & swim center .25 miles this. property is duplex. Very separate accommodations! Private!

4.91 out of 5 average rating, 120 reviews

A pinball machine stands against a gray wall, adorned with colorful graphics. A cozy gray sectional couch is positioned nearby, complemented by a small yellow table. Natural light filters through a window, enhancing the inviting atmosphere of the entertainment space.

Guesthouse in Louisville

Prime Location, Private, games, pinball Fun!"

Welcome to your home away from home! This charming 2-bedroom house is located on our property but offers private access and private fenced area. The house features a pinball machine, board games, a Nintendo Switch, and an Xbox—perfect for relaxing after a day of exploring Louisville. Tucked away on a quiet dead-end street, this home offers private driveway parking and convenient highway access.

4.93 out of 5 average rating, 1,017 reviews

A blue carriage house is presented, featuring a spacious driveway with a two-car garage below. A staircase leads to the upper level, framed by a tree dusted with snow, creating a serene winter scene.

Guesthouse in Louisville

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.

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Popular amenities for Windy Hills vacation rentals

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Other great vacation rentals in Windy Hills

5 out of 5 average rating, 7 reviews

A bright kitchen features white cabinetry and blue accents. The countertop includes modern appliances, with a black stove and a microwave. Natural light enters through a window, highlighting the cooking space. A small dining table is set nearby, and glass doors lead to the outside deck.

Apartment in Brooks

Cozy Studio in Brooks

JeanneRating, 5 stars1 week ago

Ron and Laurie are excellent hosts. They communicated well and checked in to ensure I was comfortable. The studio space was clean, well furnished, and accommodates guests well. We stayed for 3 nights and felt right at home. The bed is on the softer side and there are a few steps; it's also near a train line, but it's not too busy or disturbing. Overall, it was conveniently located for a stay in Louisville or the surrounding area. I would stay here again.

A white, multi-door wardrobe is positioned against a wall, featuring louvered panels and multiple drawers at the bottom. A door is visible in the background, leading to another space, while light oak flooring adds warmth to the area.

Apartment in Louisville

5 out of 5 average rating, 4 reviews

New basement apartment

PaulRating, 5 stars9 months ago

One of the best experiences yet! Easy to find and get in. We were visiting kids and even had a couple the grandkids spend a couple of nights with us. Liz was very friendly and has done a great job putting this place together. We will definitely stay again when we are in town.

Private room in Jeffersonville

A wooden shelf displays a variety of glass jars filled with herbs, each labeled with black chalkboard stickers. Below, a set of copper mugs hangs from a rack. The background features light green walls, contributing to a cozy and organized kitchen atmosphere.

4.96 out of 5 average rating, 817 reviews

Boho Suite minutes from downtown!

EmilyRating, 5 stars2 weeks ago

Tamyra has a wonderful home with everything you need for a short stay. She has put a lot of effort into creating such a peaceful, serene place to enjoy. We loved her garden and ducks, and also appreciated the coffee/ breakfast bar she provided. This spot is a perfect little getaway and highly recommend.

4.94 out of 5 average rating, 72 reviews

Apartment in Louisville

Highlands Haven I

LexusRating, 5 stars1 month ago

Very comfortable, quiet & felt right at home. Overall great place to stay !

A game table is featured, designed for shuffleboard play. The smooth wooden surface, dusted with white powder, presents multiple scoring areas. Distinct circular pucks are positioned on the table, indicating an ongoing game. The overall setting reflects a recreational atmosphere.

Guesthouse in Louisville

4.85 out of 5 average rating, 26 reviews

Cute Louisville Carriage Apt - Game Room -Sleeps 4

TonyRating, 5 stars1 month ago

This was the place I needed for the weekend. It was very Peaceful and the place was so nice, clean and relaxing! Maria was so nice and very easy to communicate with. I would recommend this place to everyone.

The open-concept living space showcases a modern kitchen with granite countertops and stainless steel appliances. A dining area with a round table sits adjacent to the kitchen, while a comfortable seating arrangement is visible in the background under natural light from large windows.

5 out of 5 average rating, 13 reviews

Louisville Retreat w/ Deck ~ 11 Mi to Downtown!

TracyRating, 5 stars2 weeks ago

House was just as it was in the listing, great location close to everything, beautiful home and comfortable beds!

An outdoor deck features a seating area with a spacious sofa and chairs, surrounded by greenery. A barbecue grill is positioned nearby for convenient outdoor cooking, and a basketball hoop can be seen in the background, adding recreational options to the space.

4.71 out of 5 average rating, 21 reviews

*Prime Location | Renovated | Close to everything

TheresaRating, 5 stars4 weeks ago

Christine was super easy to work with. My fur baby and I were right at home. Everything was perfect. Will for sure be returning!