Vacation rentals in Woodlawn Park

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Top-rated vacation rentals in Woodlawn Park

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Guest favorite

A modern kitchen features dark cabinetry and a large island with seating for two. Natural light pours in through a window, illuminating the white subway tile backsplash and stainless steel appliances. Wooden ceiling beams add character to the airy space.

Apartment in Cherokee Triangle

4.94 out of 5 average rating, 288 reviews

Chic, Luxurious Carriage House in Ideal Location

Selected by Architectural Digest as best Airbnb in Kentucky. Sink into the rounded, studded armchair under exposed wooden beams at a characterful retreat with minimal, modern style. This historic space contrasts deluxe touches including the 6-foot soaking tub with sash windows and a sliding barn door. This fully furnished apartment is perfect for a getaway weekend or for short to medium rental as an executive apartment. The historic property has been lovingly renovated as a luxurious apartment with high-end finishes while maintaining the historic character of its past as a carriage house. You enter the apartment through a hallway that houses a dedicated washer and dryer. Upstairs features a large living/working space, a beautiful kitchen with brand new-high end appliances, and a 50" 4K smart TV. The sliding barn door separates the bedroom, where you will also find a large walk-in closet, a marble bathroom with a 6 foot soaking tub, and a brand new queen sized Tuft and Needle mattress. We will meet our guests and orient them to the house and neighborhood, or provide self check-in depending on preference. For the remainder of your stay, we will be close by for any additional needs. Cherokee Triangle is one of the most historic neighborhoods in Louisville, built in the late 19th century and part of the larger Highlands area. The tree-lined streets are a short walk from the restaurants, bars, and boutiques on Bardstown Road. You do not need a car around here - everything is a short walk away. Parks, restaurants, shops, grocery stores are all within 5 minutes on foot. Downtown or Churchill Downs are is a 5-10 minute drive away. Street parking is available.

Guest favorite

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

4.94 out of 5 average rating, 108 reviews

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.

Top guest favorite

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.

Guest suite in Louisville

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.

Top guest favorite

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

5 out of 5 average rating, 214 reviews

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.

Guest favorite

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

5 out of 5 average rating, 129 reviews

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.

Guest favorite

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.

Home in Clifton Heights

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.

Guest favorite

A narrow hallway is lined with white doors leading to different rooms. A large wooden clock with black numerals is mounted on a green wall, providing a point of interest. A rug with a decorative pattern runs along the polished hardwood floor.

Home in Louisville

4.87 out of 5 average rating, 212 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.

Top guest favorite

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.

Home in Louisville

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*

Top guest favorite

Apartment in Louisville

4.96 out of 5 average rating, 303 reviews

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.

Guest favorite

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

4.85 out of 5 average rating, 255 reviews

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.

Top guest favorite

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

4.96 out of 5 average rating, 142 reviews

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!

Guest favorite

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

4.91 out of 5 average rating, 120 reviews

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.