See all properties
Entire home

"Highlands Lookout: Your Gateway to Louisville's Ultimate Adventure!"

Vacation home near Kentucky Exposition Center in Louisville

Choose dates to view prices

Photo gallery for "Highlands Lookout: Your Gateway to Louisville's Ultimate Adventure!"

A grand piano, a blue upholstered chair, and a modern staircase with glass railings and wooden steps.
A two-story building with a white facade, a balcony with a railing, and a door marked "1030".
A modern kitchen with dark wood cabinets, stainless steel appliances, granite countertops, and a built-in dishwasher.
Dining
Terrace/patio

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms4 bathroomsSleeps 82000 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
  • Outdoor Space
  • Parking available

Explore the area

View in a map
Louisville, KY
  • Place, Cave Hill Cemetery
    ‪9 min walk‬
  • Place, Cherokee Park
    ‪17 min walk‬
  • Place, Nulu Market Place
    ‪2 min drive‬
  • Airport, Louisville, KY (SDF-Louisville Intl.)
    ‪10 min drive‬

Room options

You may also like

Ad
3 bars/lounges

Derby City Gaming & Hotel - A Churchill Downs Property

Louisville
  • Parking included
  • Free WiFi
  • Restaurant
  • Air conditioning
9.4 out of 10, Exceptional, 2,362 reviews
$107 nightly
The price is $126
Jul 22 - Jul 23
Total with taxes and fees
Derby City Gaming & Hotel - A Churchill Downs Property

About the neighborhood

Louisville

In Louisville .You'll be within half a mile (1 km) of Cave Hill Cemetery and 2 miles (3 km) of Cherokee Park with a stay here. Headliners Music Hall and Nulu Market Place are also within 2 miles (3 km).
View more Vacation Homes in LouisvilleOpens in a new window

What's nearby

  • Cave Hill Cemetery - 9 min walk - 0.5 miles
  • Cherokee Park - 17 min walk - 0.9 miles
  • Muhammad Ali Gravesite - 19 min walk - 1.0 mile
  • Headliners Music Hall - 20 min walk - 1.1 miles
  • Nulu Market Place - 2 min drive - 1.5 miles

Getting around

  • Louisville, KY (LOU-Bowman Field) - 10 min drive

Restaurants

  • ‪Chill BAR Highlands - ‬3 min walk
  • ‪O'Shea's Irish Pub - ‬4 min walk
  • ‪McDonald's - ‬6 min walk
  • ‪Big Bar - ‬5 min walk
  • ‪Starbucks - ‬4 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

"Highlands Lookout: Your Gateway to Louisville's Ultimate Adventure!"

"Welcome to Highlands Lookout: A Modern Retreat for Your Louisville Adventure!

Step into contemporary comfort on Bardstown Road in the lively Highlands of Louisville! Ideal for guys' or girls' weekends, concerts, and conventions, our space boasts new, modern amenities for your ultimate relaxation. Immerse yourself in the vibrant atmosphere of "Keeping It Weird" as you unwind on our balcony or chill out on the lower porch. With a focus on cleanliness and comfort, our retreat is perfect for those seeking a pristine stay. Close to distilleries, bars with rare bourbons, downtown, racetrack, and the airport—Highlands Lookout is your gateway to a thrilling Louisville experience!"

While we don't live on-site, we're locals in the area and know the Highlands like the back of our hands. Our home is your gateway to this vibrant community. Skip the guidebooks—we're here to help with personalized suggestions, from the best dishes at local restaurants (and trust us, there are TONS) to hidden gems in the area. Whether you prefer recommendations or want to explore on your own, we're here to ensure your stay in the Highlands is everything you envision. Welcome to our home!

///ADDITIONAL REQUIREMENTS PRIOR TO CHECK IN///
Our guests are required to complete a separate host rental agreement that will be sent to you after booking. Additionally, a credit card and photo id will be required to authorize a $200 security deposit hold. This hold will be released upon checkout as long as no damages or excess mess is done at the property.

Similar properties

Dining
Cambria Hotel Louisville Downtown-Whiskey Row
Downtown Louisville
  • Pool
  • Pet friendly
  • Free WiFi
  • Restaurant
4.7 out of 5, Exceptional, 1,010 reviews
$99 nightly
The price is $117
Aug 9 - Aug 10
Total with taxes and fees
Cambria Hotel Louisville Downtown-Whiskey Row

Property amenities

Internet

  • Available in the house: WiFi

Parking and transportation

  • Car not required
  • Parking on site

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 3.5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Living room

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a health/beauty spa
  • Near a hospital
  • Near a zoo
  • Near the marina

Things to do

  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Jet skiing nearby
  • Motor boating nearby
  • Spelunking nearby
  • Swimming nearby
  • Theme park nearby
  • Wildlife walks nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Property does not allow children
  • Unit size: 2,000 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 22

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • No pets allowed

Children and extra beds

  • This property does not allow children.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.

Property Registration Number STR929688

Property is also known as

In the Middle of Everything Louisville
In the Middle of Everything Private vacation home
In the Middle of Everything Private vacation home Louisville

Frequently asked questions

How close is "Highlands Lookout: Your Gateway to Louisville's Ultimate Adventure!" to the airport?

This vacation home is 4.4 mi (10-min drive) away from the Louisville, KY (LOU-Bowman Field) airport, the closest popular airport to the property.

Does "Highlands Lookout: Your Gateway to Louisville's Ultimate Adventure!" have an airport shuttle?

Airport shuttle services are not available at this vacation home.

Does "Highlands Lookout: Your Gateway to Louisville's Ultimate Adventure!" offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at "Highlands Lookout: Your Gateway to Louisville's Ultimate Adventure!"?

No, there is no casino at this vacation home, but Horseshoe Southern Indiana Casino (26-min drive) is nearby.

What time is check-in at "Highlands Lookout: Your Gateway to Louisville's Ultimate Adventure!"?

Check-in begins at 4:00 PM.

Is there free parking at "Highlands Lookout: Your Gateway to Louisville's Ultimate Adventure!"?

Free parking is not available at this vacation home.

Does "Highlands Lookout: Your Gateway to Louisville's Ultimate Adventure!" have a pool?

This vacation home does not have a pool.

Does "Highlands Lookout: Your Gateway to Louisville's Ultimate Adventure!" have a spa?

There are no spa services available at this vacation home.

How close is "Highlands Lookout: Your Gateway to Louisville's Ultimate Adventure!" to downtown Louisville?

This vacation home is 2.1 mi away from Louisville.

"Highlands Lookout: Your Gateway to Louisville's Ultimate Adventure!" Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 33 out of 35 reviews
Rating 8 - Good. 2 out of 35 reviews
Rating 6 - Okay. 0 out of 35 reviews
Rating 4 - Poor. 0 out of 35 reviews
Rating 2 - Terrible. 0 out of 35 reviews

10/10

Cleanliness

Reviews

Verified

10/10 Excellent

Joe K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our group of 6 adults thoroughly enjoyed our stay. The location is excellent, the home was clean and spacious, and we all enjoyed friendly Pac-Man competitions!I highly recommend this property!
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Todd M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect spot with plenty of things in walking distance, not far from downtown louisville
Stayed 3 nights in Nov 2025
Verified

10/10 Excellent

Deb P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

WI Travelrs

Had a great time, location was perfect.
Stayed 2 nights in Sep 2023
Verified

10/10 Excellent

Allison T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Place

This is the second time staying at this property. It’s well stocked, clean, and located in a great location!
Stayed 2 nights in Apr 2025
Verified

10/10 Excellent

Michael D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family trip

Great location and nice property. Host made checking in and checking out simple.
Stayed 2 nights in Mar 2023
Verified

10/10 Excellent

Roxanna

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great property, perfect location

Couldn’t have been happier with the cleanliness.
Stayed 4 nights in Sep 2024
Verified

10/10 Excellent

Molly E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place!

Everything was honestly so easy and perfect. Would very much recommend
Stayed 1 night in Mar 2025
Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect stay. Great alternative to downtown hotels

We had a great stay at this beautiful home. It was perfectly appointed and had everything we needed. Great location, close to downtown, in a cool swanky neighborhood. 5 stars
Stayed 1 night in Jun 2022
Verified

10/10 Excellent

Connie R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was exactly as described! Very well stocked and beautifully decorated and updated! Lots of space, the bedrooms were large, 3 full and another half bath made everything so easy!
Stayed 2 nights in Aug 2025
Verified

10/10 Excellent

Michael C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property is well located and very modern and comfortable. When I come back to Louisville, I would hope that this property is available. I would definitely return.
Stayed 2 nights in Sep 2025
Verified

10/10 Excellent

Allison T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fun!!

It was a great place in a great location! We walked almost everywhere. It was such a fun vacation!
Stayed 3 nights in Sep 2023
Verified

10/10 Excellent

Thomas D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great weekend!

We ventured to Louisville for a family wedding. Had a wonderful stay! We could walk to restaurantS/Bars. Had a great stay. Beds were comfortable and the place was spotless. One of the most well stocked VRBO's that we have stayed in. We will rent here again.
Stayed 4 nights in May 2024
Verified

10/10 Excellent

jon c.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beyond Expectations!

Location, bedrooms and overall entertaining spaces were excellent! Would definitely recommend! 5 out 5!
Stayed 3 nights in May 2023
Verified

10/10 Excellent

Becky B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful

We had a wonderful stay in Louisville at the Highlands Lookout house. Sally was a such an incredible host. Communication was spot on, parking was perfect and we had 4 cars, the house was spotless, there were special touches throughout, a wonderful front porch to enjoy the night life, walking distance to many bars and restaurants. Would definitely stay here again! Thank you, Sally for a terrific stay.
Stayed 2 nights in May 2024
Verified

10/10 Excellent

Rich W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Golf

Great! Everything we hoped for and many extra amenities. Thanks
Stayed 2 nights in May 2024
Verified

10/10 Excellent

James B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great House in Highlands

The house is beautiful and well setup for our group of 6. The kitchen is very large and has everything you need. The beds were extremely comfortable. The outdoor balcony on the second floor was great as you can relax and watch the neighborhood at night. Only item is the parking lot as there is a couple of large holes by the street. Definitely would stay here again for sure.
Stayed 4 nights in Apr 2024
Verified

10/10 Excellent

Theron B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Highlands Lookout

The property was located in very close proximity to most of my senior family who lives in Louisville. Sally, the host was wonderful when we arrived. Although we didn't need her during our stay, she let us know that she was or would be available anytime. If available, we will stay at Highlands Lookout every time. Thank you Sally
Stayed 4 nights in Nov 2024
Verified

10/10 Excellent

Diana D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

The house was perfect for our one night stay, wish we had longer to explore the city, and just the surrounding area but as it was we walked to dinner, walked for drinks, aside from the narrow back alley for parking it was perfect. And that was only due to us getting a huge suv for the rest of our trip and being unused to driving in small spaces like that. -
Stayed 1 night in Oct 2022
Verified

10/10 Excellent

Amanda K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Better than expected!!

Lovely house, comfy and very recently updated. Way bigger than the photos show. Nice modern amenities. A cool but very eclectic neighborhood…random zoning and some sketchy people around but they mostly stay to themselves. Loud on the weekends but right in the action! Very well stocked…would stay again!
Stayed 7 nights in Oct 2022
Verified

10/10 Excellent

alannah n.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay!

This place is lovely! It was clean and well equipped. Lots of space to hang out inside and out! Perfect location to get the bourbon trail easily!
Stayed 4 nights in Oct 2022
Verified

10/10 Excellent

Lisa O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Ladies Trip

We had a great experience at Highlands Crossing! Sally was a gracious and responsive host & the house was clean and beautiful. We would definitely go back.
Stayed 1 night in Sep 2022
Verified

10/10 Excellent

Terry S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome location!!!

The location was perfect. Right in the middle of the Highlands area that has numerous bars and restaurants. House has obviously been recently renovated and is in perfect condition. No problems getting access to the house. And although there is a bar Highlands Tap Room right next door it was never a problem and was a fun place to have a drink and/or meal. A special shout out to the Bristol Bar & Grille just up the street which had great food.
Stayed 3 nights in Aug 2022
Verified

10/10 Excellent

Jan M.

Liked: Cleanliness, check-in, communication, listing accuracy

Great House

This house was very nice, clean and welcoming. Easy check in and out. The only thing I would mention to potential guests is the night life over the weekend nights. It was after 3:00 am both nights before the street was quiet, making sleep difficult. This of course is out of the control of the owner. Loved the house otherwise.
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Rozina D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spotless, spacious house in a great location!

Very impressed with this rental. It's bigger than what you see in the pictures. Spotless! Location is great if you are looking for restaurants and bars within walking distance. We also went on walks in the neighborhood for some quiet. Short drive to distilleries in downton (just make sure their tasting bars are open before you go). We were able to check out late which was a bonus. Highly recommend this place!
Stayed 4 nights in May 2022
Verified

10/10 Excellent

Jennifer E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Stay

We were in town for the Kentucky Derby and had six adults in our group. This house was perfect! We would absolutely book this home again! It was clean, spacious, and had all of the amenities that we needed. It’s within walking distance to plenty of good restaurants and fun bars. The parking area is a little tight for a large SUV, but cars smaller than a suburban wouldn’t have a problem. It wasn’t an issue, just took a little creative maneuvering. The street is lively (& occasionally noisy) and there’s a great eclectic vibe in the neighborhood. We loved it! The hosts were extremely friendly and quick to respond to our few questions. 10 out of 10 we’d return!
Stayed 4 nights in May 2022

Explore More Ways to Travel with Travelocity