Holiday rentals in St. Regis Park

Bourbon Trail Estate | 3 Epic Acres | 7 Bed 6 Bath

Welcome to your ultimate Louisville getaway! 🏡 This private 5BR retreat blends space, comfort, and style with unbeatable access to the Bourbon Trail, dining, and attractions—perfect for families or groups. ✨ Spacious 5BR, 5.5BA Retreat – 7 beds (5 Kings) 🛏️ 🍳 3 Full Kitchens + Bar 🎬 Entertainment Room w/ Media System – Perfect for Game Night 🎮 🌳 Private Backyard for Dining & Relaxing 🥃 Quiet setting just minutes from Bourbon Trail, Shopping & Top Attractions A serenity-meets-convenienc

Spacious 4 BD Home | 5 min to Airport • 6 min Expo

Your Louisville home base! Nestled in the highly desirable Upper Highlands this stylish retreat offers convenience, comfort, and charm for families, business travelers, events, and weekend explorers.Whether you're here for the Kentucky Expo, flight at SDF, downtown adventure, or a fam getaway Prime Location: 5 minutes from Louisville Muhammad Ali International Airport Around 6 min to the Kentucky Exposition Center & Freedom Hall Easy drive to downtown’s Bourbon District, Yum! Center, and more

The Lakehouse at Progress Park in Derby City

Skip the packing & extra costs - everything you need is already here. Perfect for groups, families, or midweek getaways. The Lake house combines comfort, convenience, & a one of a kind outdoor experience. Enjoy your own private space PLUS access to boating, games, & more. All included with your stay. Show up, settle in, and start relaxing. Progress Park has 11 total units on site. 2 houses, 8 airstreams & a bunk house. *KY DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

The Sweet Spot! - Live Like a Local

Live like a local in one of Louisville’s most sought-after neighborhoods, young professionals and families alike. Rich in history and surrounded by wall-to-wall dining, shopping, and entertainment, this vibrant area is known for its charm, energy, and premium appeal. Originally built as a single condo over two decades ago, the owner later acquired the neighboring unit and completely reimagined the entire second level. The result is a thoughtfully crafted space that truly feels like a retreat.

Hidden Gem | Stylish Comfort | Prime Location

Welcome to our newly remodeled 4-bedroom, 2.5-bathroom family home. Ideal for families, it features a king master suite and two queen beds and a double. Located in a relaxing, family-friendly neighborhood behind major hospitals, it's close to TOP GOLF, Expo, Oxmoor Center, St Matthews Mall, downtown, and Churchill Downs. Enjoy the vibrant nightlife, bourbon trail, parks, and shopping. The brand-new remodel includes modern appliances, and the spacious backyard is great for gatherings.

Colonial Hideout | Close to fairgrounds!

Ready for a relaxing stay in Louisville, Kentucky?! Welcome to a wonderfully homey stay minutes away from the KY Expo Center & Kentucky Fair Grounds. Perfect for hitting the Kentucky Bourbon Trail, heading to one of Louisville's many events, or heading to a game at the KFC Yum! Center. The property & driveway can easily manage horse trailers and car trailers if you’ve got a lot to haul. We look forward to hosting you! Family Ready: Pack n Play, High Chair, Plastic Plates & Cups

OPEN 4BR/2BA • Sleeps 8 • Near Hwy • Covered Deck

Quiet 4BR/2BA home for 8 with covered deck and easy highway access. Perfect for families or groups, this spacious retreat offers an open kitchen, dining, and living area with a large table so everyone can gather for meals or games. Guests love the roomy layout that allows for both togetherness and privacy. Two bedrooms and a full bath are downstairs, with two more bedrooms and a second bath upstairs. Enjoy the big backyard, private parking for 3 cars, and in-home washer/dryer.

Lumos Stays: 65" 4K TV, memory foam, kid-friendly

Michael and Ashley (Lumos Stays) welcome you to Louisville, home of bourbon! Centrally located, minutes from the interstate, and close to downtown and the bourbon trail, this is your home base for adventure. Enjoy the 65" 4K Roku TV, fast wifi (~317mbps), green tea memory foam mattresses, modern kitchen, kid-friendly amenities… and did you see that outdoor space? Solo Stove fire pit, hammock, propane grill, and games. Enjoy the private fenced-in backyard and large driveway!

Centrally Located•4 Bedrooms•2 Full Baths•Backyard

Looking for a place to stay in Louisville with your family? This 4 Bedroom House is perfect! With a central location and private yard, this property offers everything you need for a comfortable stay. • 1 Bedroom with 1 King bed • 1 Bedroom with 1 Queen Bed • 1 Bedroom with 1 Queen Bed • 1 Bedroom with 2 Queen Beds • Private deck and yard • Central heat and air • Roku TV and Amazon TV • FREE Parking *Bowflex in the basement can be used at your own risk!

Spacious East End Louisville retreat near downtown

Stay in this modern East End Louisville home designed for comfort and flexibility. Featuring 3 bedrooms, 4 beds, a bonus sleeping area, and 3 full bathrooms, the layout comfortably sleeps up to 8 guests in beds across two spacious levels. Perfect for traveling nurses, business stays, Derby trips, or Bourbon Trail visits, with quick access to hospitals, dining, shopping, and downtown Louisville. A clean, stylish, and convenient home base for any stay.

Olive Branch Suite with projector screen in E Lou

This suite is a beautiful private retreat complete with a projector for watching your favorite streaming service for the ultimate movie night. Centrally located and within 10-20 minutes of numerous local hospitals, universities, as well as various restaurants and downtown destinations, our guest suite offers a peaceful retreat in a convenient and safe location. We also provide a fold out desk that guests can use for a remote work space if desired.

Luxe Waterfront w/Cinema Hot Tub Sauna Pet Views

Experience sweeping Ohio River views at an upscale waterfront retreat just minutes from Downtown Louisville, the Urban Bourbon Trail, and 15 minutes from Churchill Downs. Designed for up to 12 guests, enjoy a private hot tub, sauna, theater, game room, expansive riverfront deck, and fire pit—an elevated blend of luxury, comfort, privacy, and resort-style amenities for Derby weekends, family escapes, and unforgettable Kentucky getaways.