Holiday rentals with a fireplace in Highlands

Quiet Neighborhood-Close to Expo, Churchill Downs!

The Cypress Cottage is nestled in a peaceful neighborhood and conveniently located moments away from Louisville attractions such as Nulu, Caverns, Churchill Downs, and Bourbon Trail. Designed thoughtfully to give cozy, yet modern vibes, features that stand out: ✔5 Beds ✔2 Full Baths ✔Remodeled Kitchen ✔Dining & Breakfast Area ✔Fireplace ✔Game room ✔2 Smart TVs ✔Fast Wi-Fi (500 Mbps) ✔Washer & dryer ✔Carport ✔Firepit ✔Private Backyard ✔Outdoor Grill Book with us and you will be glad you did!

The DerbyBirdie - The Highlands (by Tyler Park)

The DerbyBirdie would love to welcome you on your next trip to Louisville! This well-appointed second floor private apartment has all the comforts of home. Charmingly situated in the verdant Tyler Park neighborhood, AND within safe walking distance to Bardstown Rd, Germantown, & Old Forrester’s Paristown Hall. Also less than 4 miles from Churchill Downs, University of Louisville, The KY Expo / International Convention Center & Downtown. Perfect for couples or more private Individuals. Come Stay!

ArTisTs CoTTaGe

Enjoy peaceful privacy with center city convenience! Bright, open ambiance. Art and music supplies, books, toys, games, CD's, movies. Two decks and a covered patio. Found art gardens and galleries. Fully equipped kitchen with granite counters. Large windows in downstairs bedroom with queen bed and gas fireplace. Ladder access to queen bed in skylit loft. A perfect getaway for artists/writers on retreat, solo adventurers, couples, business travelers and small families with well behaved kids.

Fully Renovated 1960s Urban Chic Deer Park Retreat

Sprawl out on a chic, mid-century sectional amid the retro flair, eclectic artwork, and vaulted ceilings within this captivating loft-style home. Cook dinner in a kitchen with soapstone surfaces and dine al fresco at an old-school table on the patio. Completely renovated with all new luxury hotel bedding, while keeping the original hardwoods, and charm of this older home. Two bedrooms on the 1st floor and two on the 2nd, easy access for all ages. 10 min, to downtown and the Expo Center.

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.

The Burb Inn - Nulu & Downtown *w/Firepit*

The Burb Inn is a hip place to stay in the Phoenix Hill/NULU district of Louisville. Easy access to top rated restaurants, bars, and attractions. Great place to host a group of friends, family or smaller bachelor party. Includes private parking, yard & fire pit. Upon entering there is a living area perfect for entertaining with 16’ ceiling & sleeping loft above the kitchen area. Upstairs has two bedrooms with queen beds each with private half bath. There is a separate private shower room.

Private EAST END gem, minutes to everything!

Cozy, East End cottage just minutes from Top Golf, shopping malls, restaurants, entertainment, and other amenities. Easy access to the expressway. Home is well appointed with granite countertops, stainless appliances, hardwood floors, and more. A seasonal creek across from the house can be heard giving the impression of a cabin in the woods with privacy and seclusion, with the convenience of city living at your fingertips. There is also a beautiful park steps away from the house.

4th Street Suites - Beautiful King Bed Suite

Wake up to the best of Louisville! Imagine starting your morning in a cozy king bed, strolling to 4th Street Live for brunch, and exploring nearby restaurants, bars, and theatres. Spend the afternoon lounging by the pool or soaking in the hot tub, then watch the city lights twinkle from the 7th‑floor terrace. This stylish suite is your launchpad for urban adventure—and a quiet, relaxing escape when it’s time to rest. Come make it yours and experience the heart of the city!

The Old Fashioned~Luxury 1BR~Stay Nulu Marketplace

BNB Louisville presents "The Old Fashioned!" 🥃 Experience this spectacular unit in Louisville's hottest urban development, NULU Marketplace. • Luxurious 1-Bedroom Suite (King Bed + Sofa Bed) 🛏️ • Historic Charm: Exposed brick, high ceilings, & pocket doors • Spa Bathroom with Soaking Tub 🛁 • Full Kitchen & In-Unit Laundry • Secure Off-Street Parking Included 🚗 Located steps from breweries, shops, and dining. Perfect for a romantic getaway or stylish city retreat!

Perfect Nulu Getaway w/ Best Location- low fees

You can’t find a better location in the city. Welcome to Lou Lou on Washington, our Nulu condo. We are located just steps away from the best food, drinks, and events in the derby city. We are located on a quiet street, only one block away from Main St. You can walk to breweries next door or even a soccer game at Lynn Family Stadium. The Yum Center is only a few blocks away, and we have one of the few properties located walking distance from Waterfront Park.

Quaint Highland's Bungalow

Kick back and relax in this calm, stylish space with equal proximity to beautiful Cherokee Park and all the shops and restaurants on Bardstown Road in the popular Highland's neighborhood. Two bedroom, one and a half bath, completely updated one hundred-year-old home. The backyard offers a beautiful firepit with Adirondack chairs, a patio with dining area and Traeger Grill and plenty of room in the landscaped backyard to throw a ball. Three day minimum stay.

MARYLAND HOUSE - Highlands luxury, WALK TO ALL

Superhost Property! Very safe location, Front porch w/swing 1st-floor master with ensuite bath w/Jacuzzi 3 Bedrooms, 2 Full Baths Street Parking for 2 vehicles Well stocked, full kitchen Koi pond off Master Bedrooms Tasteful arts and crafts design/decor On-site washer and dryer 4.9 Miles to Expo Center/Airport Churchill Downs 4.2 Miles to Downtown & Distilleries Less than 1 mile to Cherokee Park No locals No Events Only registered guests, Please.