
Holiday rentals with outdoor seating in St Matthews
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in St Matthews
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

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.

Quiet Neighborhood Home With Outstanding Location
Situated on a quiet hilltop neighborhood in Clifton Heights, this is the perfect location for a professional or personal visit to Louisville and very animal friendly. It is within 10 minutes of Downtown, Waterfront Park, Nulu, Frankfort Avenue, the Highlands, the Convention Center, and just 15 minutes from historic Churchill Downs. These neighborhoods feature the best dining and entertainment in the city. Just a block away is the Mellwood Arts Center complex with shops and dining.

Downtown Apt • Pool, Hot Tub + Golf Simulator
Live in luxury while being in the heart of it all! This centrally located space has all of the amenities and ambiance for a lavish getaway! Enjoy a peaceful nights sleep on a king bed, and wake up to a complementary cup of coffee! Get a workout in at our state-of-the-art gym, or explore everything Louisville has to offer right from your doorstep! With tons of bars, restaurants, live music, and other activities within a block, you'll never be bored! Book your stay with us today!

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.

The Jungalow: 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 (~387mbps), 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!

Eclectic/Modern 1 BR in Clifton!
Updated 1 bedroom/1 bathroom stylish retreat right in the heart of the Historic Clifton neighborhood. Clifton is directly off Frankfort Avenue near the Highlands, Nulu, St Mathews, and Old Louisville neighborhoods. This 600 sq ft charming shotgun home was built in the 1900’s and it has a ton of character and “old home” charm, while still having updated features throughout. This home is very close to many restaurants and shops! You can walk, drive, or bike to Frankfort Ave.

4th Street Suites - Luxury 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.

Comfortable-relaxed space to find your inspiration
Located in the Germantown neighborhood of Louisville, this peaceful efficiency apartment in a traditional "shotgun" home, built in the 1890s, is within 10 minutes of nearly all of Louisville’s airport traveler’s attractions. Guests enjoy great sleep on top bedding and attention to detail. Sit on the front porch and let time slip by or spend the evening with a relaxing drink or meal in one of the neighborhood’s hip local eateries and bars. Plan your next journey.

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.

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.

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.
Popular amenities for outdoor seating rentals in St Matthews
House rentals with outdoor seating

Colonel Lou Lou's

king bed and oasis backyard with hot tub

Newly Updated: Spacious Suite/Private Entry

"Call Me Old-Fashioned" in Derby & Bourbon Country

Lil Blue-Cheerful, fully renovated & updated home

502 House @ Progress Park w/ Game Room

Urban oasis close to breweries, distilleries &more

Cheerful 2 bedroom home, close to downtown
Apartment rentals with outdoor seating

★ Victorian Louisville ★ Beautiful 1200 sqft Apt

Lucky Horseshoe

Falls City Loft - Free parking!

Downtown Luxury 1BR Apt near Louisville KY

Renovated Riverfront Apartment with Elevated Deck

Classy Urban Condo with Great Views

Dreamy Designer-Curated Shoppable Retreat

Home Away from Home, Unit 3
Apartment rentals with outdoor seating

Cherokee Park / Highlands Charm

Hidden GEM, newly furnished in a safe, great area

The Old Fashioned~Luxury 1BR~Stay Nulu Marketplace

Spacious Riverfront Condo Minutes from Downtown!

Luxury Apartment/Near Louisville/EV Charger

Downtown Condo | Private 1 CAR Garage & Balcony

Charming Penthouse/Rooftop Patio/Downtown

The Greatest penthouse in the heart of city
When is the best time to visit St Matthews?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $202 SGD | $205 SGD | $244 SGD | $288 SGD | $385 SGD | $216 SGD | $223 SGD | $190 SGD | $281 SGD | $250 SGD | $214 SGD | $225 SGD |
| Avg. temp | 2°C | 4°C | 9°C | 15°C | 20°C | 25°C | 27°C | 26°C | 22°C | 16°C | 9°C | 4°C |
Quick stats about holiday rentals with outdoor seating in St Matthews

Total holiday rentals
Explore 40 holiday rentals in St Matthews

Nightly prices starting at
St Matthews holiday rentals start at $51 SGD per night before taxes and fees

Verified guest reviews
Over 1,800 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
40 of St Matthews holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across St Matthews rentals

4.9 Average rating
St Matthews stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with outdoor seating Jefferson County
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- Buffalo Trace Distillery
- Kentucky Kingdom & Hurricane Bay
- Kentucky Derby Museum
- Valhalla Golf Club
- Angel's Envy Distillery
- Muhammad Ali Center
- Charlestown State Park
- Heritage Hill Golf Club
- Louisville Slugger Field
- Louisville Slugger Museum & Factory
- Turtle Run Winery
- Big Four Bridge
- Falls of the Ohio State Park
- Kentucky Science Center
- Waterfront Park
- River Run Family Water Park
- Hurstbourne Country Club
- Big Spring Country Club
- Frazier History Museum
- Evan Williams Bourbon Experience
- Rising Sons Home Farm Winery
- Best Vineyards
- Bruners Farm and Winery
- Lovers Leap Vineyards and Winer




