Holiday rentals in Kingsley

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.

4.99 out of 5 average rating, 274 reviews

★WorldlyHighlands★LARGE Kitchen, FASTWifi, Parking

Upper Highlands home in privileged location w/ keyless entry. A block from Bardstown Road, close to I-264 for fast commutes and all the HIGHLANDS excitement. Harmony of convenience & quiet allows for perfect stays for families, couples, business/vacation travelers alike. •4 bedrooms (includes basement), ALL WITH SMART TVs •Large kitchen, appliances, 2019-23 •PARKING up to 4 cars •Back porch GAS GRILL •Patio furniture * FIRE PIT, added Oct-2024 •Super Fast fiber-optic WiFi •Samsung Washer&Dryer

4.9 out of 5 average rating, 478 reviews

Your Cozy Louisville Hideaway in the Highlands

Newly renovated basement apartment in the Highlands. Safe, quiet neighborhood, dedicated off street parking and proximity to some of the best food, shopping and entertainment Louisville has to offer. Easy access to all things Louisville! -Downtown Louisville -Churchill Downs -YUM! Center -Olmstead Park -NULU -Urban Bourbon Trail -Bardstown Road -Germantown -Thriving Music and Art scene -Louisville Convention Center -Great dining and breweries -Louisville International Airport -UofL -And more!

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.

4.98 out of 5 average rating, 291 reviews

Spacious & Artsy Highlands 3 Bedroom for Up to 6

There is more room than meets the eye in this surprisingly spacious and uniquely designed space! The lower level of our house (technically the basement) is designed to be an apartment, offering 1400 sq. ft. of relaxing and spacious fun. This is a great space and value for up to six people. The space is closed off from the rest of the house with total privacy. We’re located in a quiet neighborhood in the Highlands and conveniently located to a diverse set of restaurants, highways and grocery.

5 out of 5 average rating, 213 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.

Campervan/Motorhome 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.

4.96 out of 5 average rating, 373 reviews

Cherokee Park Oasis with Private Entrance

1 bdrm basement apartment with private entrance, bedroom, bathroom, and common area located adjacent to Cherokee Park. 3/4 mile walk to shops, restaurants, and entertainment on Bardstown Rd. Heated saltwater swimming pool and cabana with wet bar. Centrally located within 10 minutes from downtown, Churchill Downs, the Zoo, the airport, golf courses,and Kentucky Kingdom. Situated in a quiet, park-like neighborhood with ample parking. Owner occupies the main floor upstairs.

4.98 out of 5 average rating, 125 reviews

Haus on Speed, charming 2nd floor apartment

Welcome to the Haus on Speed! Please note that if you have mobility issues, the apartment is on the 2nd floor and you will need to be able to climb about 20 carpeted steps. There are also 6 exterior steps when walking up from the sidewalk. Walk to anything from our charming 100+ year old Highlands home in one of Louisville's more vibrant & loved neighborhoods! This home is thoughtfully furnished to include all the comforts you could need during your stay.

4.98 out of 5 average rating, 169 reviews

Dome in Mount Washington

My Old Kentucky Dome

An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.

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.

4.95 out of 5 average rating, 327 reviews

Highlands Lower Level Studio Guest Suite

Private, well-lit, entrance is in rear of home. The space is approx. 600sq. ft. There is a gas fireplace, 42" HD TV w/Netflix & Amazon Prime. Kitchen has Keurig coffee maker, convection oven, inferred glass top burner, microwave, refrigerator/freezer w/ice, washer/dryer& a large marble shower, with heated floors in the shower room. Also space equipped w/ Medify air purifier w/H13 true Hepa medical grade filter.

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Other great holiday rentals in Kingsley

Private room in Louisville

4.97 out of 5 average rating, 531 reviews

Travelers quarters at Midlane Farm

LaurenRating, 5 stars1 week ago

Midlane Farm is Airbnb at its absolute finest! As I was walking the property and ogling the historic buildings, I thought about what a labor of love historic preservation is---and what a generous act it is to open your door to strangers. Meeting Chaz and Kim was the highlight of our stay. Their family's story is incredible, and they are doing its legacy great justice, embodying the kind of hospitality that is rare and a life enriching for those lucky enough to encounter it. We can't wait to return on another pass through Louisville. Thank you for all you do to keep it such a special place.

5 out of 5 average rating, 8 reviews

Colonel Lou Lou's

DevinRating, 5 starstoday

Perfect place to take a rest stop when passing through Louisville. Was clean and comfortable. Thanks Steven :)

Private room in Louisville

4.96 out of 5 average rating, 1,408 reviews

Large room with bath in quiet neighborhood

MarcieRating, 5 stars2 days ago

Thank you Harriet! You made my stay so much more fun and I didn’t feel alone in a new area, I felt like a had a guide! The room was cozy and comfortable, but much larger than the average hotel room. If you love exercise, the house was within walking distance to many shops and great places to eat, a little over a mile. I liked exploring the area on foot rather than by car, because I noticed interesting restaurants and shops I might not have seen of driving a rental or Uber.

Guest house in Louisville

4.96 out of 5 average rating, 67 reviews

Retro Chic Private Getaway in the Highlands.

VickieRating, 5 stars1 month ago

Great space with more room then expected. Comfortable feel and was within walking distance of my event. I would recommend this place to my friends.

4.88 out of 5 average rating, 16 reviews

Charming, Sunny Cape Cod | King BR | Hot Tub

EddieRating, 5 stars9 months ago

The house was just as advertised ! It is located in a private community with friendly neighbors and a beautiful community. We had a wonderful time with no trouble.

Private room in Crescent Hill

5 out of 5 average rating, 198 reviews

Modern Loft in Crescent Hill

JulieRating, 5 stars1 day ago

Excellent place, very safe and quiet! Mary is very welcoming and I'm really like talk with her.