Holiday rentals with a pool in Central Business District

Cherokee Park Oasis with Pool and Hot Tub

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 (seasonal) and cabana with wet bar. Hot tub. 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.

ꕥTriple CrownꕥSlp 6, HOT TUB, POOL, King Bds,&Fire

Kentucky Derby- 1st floor only ⦾Crafted for the 'gram -Murals, amenities, style ⦾ 2 bedrooms, 2 bath, murphy bed -Master ensuites, king beds, tiled bathrooms, modern kitchen, spacious areas Entertainment courtyard ⦾HOT TUB, Cowboy POOL, Sauna, Outdoor bar & Firepit seating for 12 each, Grill, BB court, outdoor rainfall shower, putt putt, shuffle board, trash pong! Best location in city! ⦾Between Highlands, 4th St Live, & NULU ⦾ 1.5 miles from YUM Center, Whiskey Row, hospitals ⦾ Free Parking

Exclusive Farmhouse w/ a Romantic Garden View!

Discover rustic charm at this serene Prospect, KY retreat, nestled on a historic estate garden by the Smithsonian. Surrounded by retired thoroughbreds and saddlebreds, this unique stay offers a peaceful farm setting just 25 minutes from downtown Louisville. Perfect for weddings, family vacations, or romantic escapes, the home features a fully equipped kitchen, outdoor space, free parking, and self check-in. Unplug, recharge, and enjoy Kentucky’s natural beauty in a truly memorable setting.

4th Street Suites - Stunning King Bed Suite

Live the best of Louisville in this sleek 1‑bed, 1‑bath downtown retreat! Perfect for couples, families, or friends, it features a cozy king bed, 2 rollaways, a fully stocked kitchen, and a bright living area. Enjoy morning coffee or evening drinks on your private balcony, stroll to nearby restaurants and bars, then relax by the pool or hot tub, play a round in the golf simulator, or unwind with a game of pool. Your launchpad for adventure—or a quiet, stylish escape when it’s time to rest!

LUX Riverfront Studio Louisville/Jeffersonville

Location! VIEW! ! DERBY! This Newly Renovated, Luxurious Waterfront Studio is the perfect home for your Family or Business trip. Ideal for The KENTUCKY DERBY, Thunder, and Bourbon & Beyond. Enjoy walking distance to restaurants, Big Four Station, the bridge to Downtown Louisville, bars, and nightlife. It’s also a short drive to Concert Venues, the KFC YUM Center, KY EXPO Center, Amusement Parks, Hiking Trails, and the Bourbon Trail. Make this your home for an Amazing Stay in Kentuckiana!

Top 1%• Yard + Porch • 3BR • Peppermint Cottage

Step into Peppermint Cottage ( breakfast included) and find the perfect blend of convenience and charm! Just 20 minutes from SDF airport, Churchill Downs, and downtown Louisville, this trendy east end haven offers an irresistible walkable lifestyle. Stroll or bike to 18 mouth watering restaurants, 14 unique boutiques, 3 pools and YMCA. Enjoy lakeside fishing, Sunday farmers markets, summer concerts, parks and summer Friday food trucks with live music . Your Louisville adventure awaits !

Explore Jeffersonville & Louisville/Book for Derby

The hot tub is available year-round. Perfect for relaxing and de-stressing during your stay. The pool is open May 1 ~ Oct 1. You can stay in and binge-watch movies from our collection of DVD's or your Apple TV app favorites on the 110-inch screen in the theater room. Please browse our photos & read the descriptions under them. You’ll love our home because we are close to downtown Louisville & Jeffersonville yet tucked away enough for a peaceful, relaxing stay. No early check-ins allowed.

The Lyric 185 - Norton Commons

Welcome the luxurious accommodations of the Lyric at Norton Commons. The Norton Commons neighborhood is an extremely walkable, mixed use development with shopping, restaurants, bars, and coffee shops. This unit is offered as a partnership with Watch Hill Proper, Louisville's premier bourbon destination. This unique partnership allows our guests the opportunity to participate in exclusive bourbon experiences, tastings, food pairings, and even private barrel selection.

Downtown Apt | King Bed • Heated Pool + Hot Tub

Stay in style and comfort while enjoying everything this apartment has to offer. Rest easy on a comfortable mattress, then start your morning with a complimentary cup of coffee. Work out in the gym, relax on the rooftop, or step outside to explore downtown just moments away. With dining, entertainment, and activities all around you, there’s always something to do. Wind down with a glass of wine and a movie on Hulu or Disney+. Book your stay and enjoy it all.

Louisville KY Home w/Hot Tub & Pool

Come celebrate the holidays Kentucky style! Bring the whole family to our beautiful 4-bedroom - We can even host your family holidays! (One room in basement with no egress), 3-bathroom Louisville retreat with a Pool (open May-Oct), Jacuzzi Spa (Year round), Mini Gym with Dumbbells, and Recreation room with other amenities. The entire house is open for your experience. Kid and Family friendly, this guest favorite home is what you've been looking for.

No Guest Fees, NEW, Bourbon, Horses, Golf Nearby

Discover your perfect retreat in Norton Commons, Prospect, KY! This home is your gateway to the Bourbon Trail, horse country, and Glen Oaks Country Club. Enjoy local dining, shopping, and community amenities like parks and live entertainment. With 4 bedrooms, 2.5 baths, and proximity to distilleries, horse farms, and golf courses, this home is ideal for families and groups. Your authentic Kentucky adventure starts here—book now!

Cozy City Condo in Norton Commons

Norton Commons – Your Perfect Getaway! This beautifully designed short-term rental combines modern comfort with timeless charm, offering an ideal stay for both leisure and business travelers. Whether you’re here for a weekend escape, a family visit, or a work trip, 9440 Norton Commons Blvd offers the perfect blend of style, comfort, and convenience. Book now and experience the best of Prospect, KY!