Apartment holiday rentals in St. Matthews

Chic, Luxurious Carriage House in Ideal Location

Selected by Architectural Digest as best Airbnb in Kentucky. Sink into the rounded, studded armchair under exposed wooden beams at a characterful retreat with minimal, modern style. This historic space contrasts deluxe touches including the 6-foot soaking tub with sash windows and a sliding barn door. This fully furnished apartment is perfect for a getaway weekend or for short to medium rental as an executive apartment. The historic property has been lovingly renovated as a luxurious apartment with high-end finishes while maintaining the historic character of its past as a carriage house. You enter the apartment through a hallway that houses a dedicated washer and dryer. Upstairs features a large living/working space, a beautiful kitchen with brand new-high end appliances, and a 50" 4K smart TV. The sliding barn door separates the bedroom, where you will also find a large walk-in closet, a marble bathroom with a 6 foot soaking tub, and a brand new queen sized Tuft and Needle mattress. We will meet our guests and orient them to the house and neighborhood, or provide self check-in depending on preference. For the remainder of your stay, we will be close by for any additional needs. Cherokee Triangle is one of the most historic neighborhoods in Louisville, built in the late 19th century and part of the larger Highlands area. The tree-lined streets are a short walk from the restaurants, bars, and boutiques on Bardstown Road. You do not need a car around here - everything is a short walk away. Parks, restaurants, shops, grocery stores are all within 5 minutes on foot. Downtown or Churchill Downs are is a 5-10 minute drive away. Street parking is available.

Apartment on Frankfort Ave: Walkout Basement

This walkout basement apartment is just 3 doors down from all that Frankfort Avenue has to offer: food, drinks, entertainment, shopping, and much more! Apartment offers a full kitchen, full bathroom, living room with Roku TV and dining nook. Enjoy coffee on the patio overlooking a large yard. Full kitchen: gas stove, refrigerator/freezer, double sink, microwave, toaster, Keurig coffee maker, electric water kettle. Full bath: full shower/bath and hair dryer Proud to be LGBTQ+ friendly hosts!

Spacious & Artsy Highlands 3 Bedroom for Up to 6

There is more room than meets the eye in this surprisingly spacious and uniquely designed space! The lower level of our house (technically the basement) is designed to be an apartment, offering 1400 sq. ft. of relaxing and spacious fun. This is a great space and value for up to six people. The space is closed off from the rest of the house with total privacy. We’re located in a quiet neighborhood in the Highlands and conveniently located to a diverse set of restaurants, highways and grocery.

Modern stay overlooking downtown

Forget your worries in this Luxury spacious and serene space. Make yourself at home! Relax in the unique 1Bedroom Queen size bed with Restaurants and smoothie bar in building! you’ll be close to Restaurants alongside the Ohio river, Kfc Yum Center, Downtown Walking bridge , Deserts , bars , music and more! Great wifi, meeting rooms open 24/7 charging stations for your electric vehicle! Last but not least Beautiful overlook of downtown Louisville on charming rooftop patio!

4th Street Suites - Deluxe 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!

Urban Bourbon Farm Loft

Very unique second story 575sqft. duplex apartment, 15 stairs to climb, with lots of amenities! A 15-20 minutes walk to reservoir park, swim club ($5.00), Blue Dog bakery, restaurants, coffee shops, salons, art galleries, a bookstore, and unique shops! The apartment is a 7 minute walk to the Southern Baptist Theological Seminary, which is a beautiful space to walk and enjoy. This is a second story apartment that is accessible through the backyard privacy fence gate.

Seneca View

700 ft² (70m²) of Open, light & airy space with modern amenities. Plz, NO smoking, toking , vaping, or any drug/cigarette use in/on property-- $300 fine. Convenient location in a quiet, sought-after neighborhood, yet within a few minutes of a bustling, busy Bardstown Road with many places to eat, shop and browse. Easy access from all major interstates: I-71, I-65 and I-64. Come stay for a week, on business (work desk is set up), or use for a fun, getaway weekend.

Haus on Speed, charming 2nd floor apartment

Welcome to the Haus on Speed! Please note that if you have mobility issues, the apartment is on the 2nd floor and you will need to be able to climb about 20 carpeted steps. There are also 6 exterior steps when walking up from the sidewalk. Walk to anything from our charming 100+ year old Highlands home in one of Louisville's more vibrant & loved neighborhoods! This home is thoughtfully furnished to include all the comforts you could need during your stay.

Beach Vibe close to Museum Row

The beach vibes here are amazing 🤩! This special place is close to everything, making it easy to plan your visit. Only 2.7 mile away you will enjoy everything Downtown Louisville has to offer from a Bourbon Experience, great places to eat, bars, museums, arts, theater, music on Main Street also known to locals as Whiskey Row and Museum Row. Enjoy the local Indiana scene in Downtown Jeffersonville or Downtown New Albany with food and fun!

The Point at Story and Frankfort Avenue

The Point is a spacious and completely renovated one bedroom (king) apartment. You will absolutely love the huge sectional couch while watching your favorite shows on the 65" smart TV. Unit very close to downtown with tons of options for local restaurants, breweries, bourbon tours and bars. Building is located in the heart of Butchertown right down the street from the new Botanical gardens, Nulu, walking bridge and soccer stadium.

Alfesco - Walkable Highlands Guesthouse

Alfresco's private and peaceful guesthouse in the heart of the Highlands is within walking distance to some of Louisville's favorite coffee shops, restaurants, and night life. Enjoy the arts, entertainment, and food of one of Louisville's most eclectic neighborhoods, or take a short drive to NuLu or downtown to explore all the city has to offer.

cellar hideaway

Studio apartment is unique and inviting. Plan a mini breakaway in this private basement retreat. New 55” TV with Netflix access or perhaps a Rip Van Winkle rest on the Queen size bed (hmmmmm so comfortable). Love to cuddle under airy light soft comforter & blankets. Walk, or drive, to stores & restaurants about 5/6 blocks away.