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*New* Speakeasy Highlands 7BR | Hot Tub | Sleep 14

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Welcome to The Trail House your stylish and moody getaway spot.
Soak in our private courtyard "speakeasy alley"
Step into the moody sipping room featuring plush velvet seating.
Relax in the stylish lounge area featuring stone walls and cool decor.
Welcome to The Trail House your stylish and moody getaway spot.

Reviews

10 out of 10
Exceptional
7 bedrooms3+ bathroomsSleeps 14

Popular amenities

  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View map
Louisville, KY
  • Place, Cherokee Park
    ‪17 min walk‬
  • Place, Headliners Music Hall
    ‪20 min walk‬
  • Place, Nulu Market Place
    ‪2 min drive‬
  • Airport, Louisville, KY (SDF-Louisville Intl.)
    ‪10 min drive‬

Rooms & beds

7 bedrooms (sleeps 14)

BR 1

1 King Bed

BR 2

1 Single Bunk Bed and 1 Double Sofa Bed

BR 3

1 Double Sofa Bed

BR 4

2 Single Beds and 1 Queen Bed

BR 5

1 King Bed

BR 6

1 Single Bed and 1 Queen Bed

BR 7

1 King Bed

3 bathrooms, 1 half bathroom

BA 1

Bathtub or shower · Toilet

BA 2

Bathtub · Toilet

BA 3

Bathtub or shower · Toilet

BA 4

Toilet

Spaces

Deck or patio
Kitchen
Balcony
Dining area

About this property

*New* Speakeasy Highlands 7BR | Hot Tub | Sleep 14

Step into The ALL NEW Trailhouse – Bourbon Retreat, a high-end, speakeasy-inspired Highlands estate designed for unforgettable Louisville stays. 🥃

Historic charm meets modern luxury with a sipping room, cocktail lounge kitchen, luxe bedrooms, and a private courtyard oasis with hot tub and fire pit. Perfect for Bourbon Trail adventures, Derby weekends, and elevated group getaways. With space for up to 14 guests, this home is tailor-made for gathering in style.

🛏️ ROOM FOR EVERYONE
Inside, you’ll find over 2,200 sq ft of character-filled comfort spread across three thoughtfully designed floors.
• Sleeping: Each of the 7 bedrooms is uniquely styled and furnished with a mix of queen, full, twin, and bunk beds, offering flexible sleeping arrangements for families, friend groups, or coworkers traveling together. All beds feature fresh, hotel-quality linens and cozy pillows for a restful night’s sleep.
• Bathrooms: Include tiled walk-in showers, a charming clawfoot tub, and double vanities—perfect for groups getting ready at once. 🚿

👨‍🍳 ENTERTAIN IN STYLE
The kitchen/lounge is a true showstopper, equipped with everything you need to cook, cater, or simply gather around the oversized island.
• Features: Stainless steel appliances, a Keurig with coffee pods and creamer, ample cookware, and plenty of dishware. It’s a central hub for the whole group. 🍳

🌿 OUTDOOR LIVING
Enjoy morning coffee on the front porch, afternoon hangs in the garden space, or unwind at night under the stars in your own slice of Highlands charm.
• Amenities: With plenty of outdoor seating, you’ll have room to spread out and soak in the experience.

📍 PRIME LOCATION
Tucked in one of Louisville’s most beloved neighborhoods, you’re truly in the middle of it all:
• 5–10 minute walk to bars, restaurants, and music venues. 🚶
• 4 minutes to KFC Yum Center and the Convention Center.
• 5 minutes to the University of Louisville.
• 9 minutes to the airport. ✈️
• Quick access to Churchill Downs, Nulu, and Downtown.
This is the perfect launchpad for exploring everything Louisville has to offer.

✨ EXCITING UPDATES
Exciting updates are on the way! A brand-new hot tub will be installed in October, and by January the home will feature a full design overhaul. The new layout will include refreshed interiors and a new bed setup with 3 king bedrooms for added comfort.

Add dates for prices

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed, service animals permitted
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Smoking

Smoking is not permitted
All guests will be required to complete a rental agreement and provide Photo ID prior to check-in. Additional house rules will be sent for your review
No Smoking/Vaping. No Pets unless authorized by host. No Local Bookings Allowed without written approval from host
A Security Hold is required and will be authorized to you credit card by the Host

Important information

You need to know

Property Registration Number LIC-STL-25-00184
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Louisville

Located in Louisville, this holiday home is near theme parks. KFC Yum Center and Louisville Slugger Museum are cultural highlights, and some of the area's popular attractions include Louisville Zoo and Kentucky Kingdom. Looking to enjoy an event or a game? See what's going on at L&N Federal Credit Union Stadium or Churchill Downs. Discover the area's water adventures with nearby power boating, or enjoy the great outdoors with cycling, hiking/biking trails and mountain biking.
View more Holiday homes in LouisvilleOpens in a new window
Map
Louisville, KY

What's nearby

  • Mid City Mall Shopping Center - 8 min walk - 0.7 km
  • Cave Hill Cemetery - 9 min walk - 0.8 km
  • Cherokee Park - 17 min walk - 1.5 km
  • Headliners Music Hall - 20 min walk - 1.7 km
  • Nulu Market Place - 2 min drive - 2.4 km

Getting around

  • Louisville, KY (LOU-Bowman Field) - 12 min drive

Restaurants

  • ‪Chill BAR Highlands - ‬3 min walk
  • ‪O'Shea's Irish Pub - ‬4 min walk
  • ‪Flanagan's Ale House - ‬5 min walk
  • ‪Chipotle Mexican Grill - ‬2 min walk
  • ‪Big Bar - ‬5 min walk

Frequently asked questions

Is *New* Speakeasy Highlands 7BR | Hot Tub | Sleep 14 pet-friendly?

No, only service animals are welcome at the property.

How much does it cost to stay at *New* Speakeasy Highlands 7BR | Hot Tub | Sleep 14?

As of 5 May 2026, prices found for a 1-night stay for 2 adults at *New* Speakeasy Highlands 7BR | Hot Tub | Sleep 14 on 29 Apr 2027 start from AU$16,034, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at *New* Speakeasy Highlands 7BR | Hot Tub | Sleep 14?

On-site parking is available at the property.

What time is check-in at *New* Speakeasy Highlands 7BR | Hot Tub | Sleep 14?

Check-in begins at 4:00 PM.

What time is check-out at *New* Speakeasy Highlands 7BR | Hot Tub | Sleep 14?

Checkout is at 10:00 AM.

Where is *New* Speakeasy Highlands 7BR | Hot Tub | Sleep 14 located?

Situated in Louisville, this holiday home is within 1 mile (2 km) of Kindred Hospital Louisville, Cherokee Park and Headliners Music Hall. Nulu Market Place and Historic Frankfort Avenue are also within 2 miles (3 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 2 out of 2 reviews
Rating 8 - Good. 0 out of 2 reviews
Rating 6 - Okay. 0 out of 2 reviews
Rating 4 - Poor. 0 out of 2 reviews
Rating 2 - Terrible. 0 out of 2 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Matthew H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This place was very clean and had a cool atmosphere. The location was good with a lot of stores and restaurants close by.
Stayed 4 nights in Mar 2026
Verified

10/10 Excellent

John D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent location, close to nightlife and bars. Off street parking is small but still accommodated a crew cab long bed truck. Plenty of beds! Hot tub was great!
Stayed 4 nights in Dec 2025

About the host

Hosted by BNB Louisville

Host profile image
Hi, I’m Eric—founder of BNB Louisville. I’ve been hosting guests in Louisville for over a decade, and I love creating unique, comfortable spaces that showcase the best our city has to offer. Whether you’re here for the Derby, a weekend getaway, or a family celebration, my goal is to make your stay seamless, stylish, and stress-free.

We’re a local team with high standards, quick response times, and a deep love for this city. From restaurant recommendations to last-minute requests, we’re here to help you feel right at home—so all you have to do is show up and enjoy.

Why they chose this property

This isn’t just another big house. It’s a well-aged Highlands retreat, crafted for groups who appreciate great company, great design, and a great pour. Thoughtfully renovated from top to bottom, this 7-bedroom estate blends historic character with modern comfort in one of Louisville’s most coveted neighborhoods.

✔️ 🥃 Sleeps 14 comfortably, with room to spread out and settle in
✔️ 🍸 Entertainer’s kitchen and lounge, perfect for cocktails and conversation
✔️ 🔥 Private courtyard with hot tub, ideal for nightcaps under the stars
✔️ 📍 Prime Highlands location, steps to top bars, restaurants, and shops
✔️ 🏇 Minutes to Churchill Downs, Downtown, and NuLu
✔️ 🎉 Perfect for Bourbon Trail trips, Derby weekends, and group getaways
✔️ 🤝 Responsive local team to support a smooth, elevated stay

Whether you’re here to sip your way through the Bourbon Trail, celebrate a milestone, or simply unwind in style, this is the kind of place that gets better every time you come back.

What makes this property unique

✅ What You’ll Love:

🛌 7 bedrooms, 3.5 bathrooms

👥 Sleeps up to 14

🛁 Hot tub

👨‍🍳 Chef’s kitchen + Keurig coffee bar

🛁 Clawfoot tub + modern tiled showers

📺 Smart TVs & blazing-fast Wi-Fi

🎯 Game yard, BBQ, & outdoor space

🚗 Easy/free off-street parking

🔑 Smart keyless entry + local support team

🌆 Walk to bars, restaurants, and attractions

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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