
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.

RIView 103. Modern Waterfront Suite Kentucky Derby
Guests can enjoy scenic views of the mighty Ohio River from any room in their private suite. Catch a beautiful sunrise or relax while sitting on the porch watching the boats and barges cruise the river. Close drive to interstate to get you to downtown Louisville to enjoy a dinner, museum, basketball game or concert in the KFC YUM Center and the world famous Churchill Downs! 1 mile away from River Ridge. We do offer a Tesla only charger or you can bring your own standard attachment for a charge.

Downtown Apt – King Bed, Hot Tub, Pool & Parking!
Stay in splendor as you enjoy the endless amenities and stylish touches this apartment has to offer! Enjoy a peaceful night's sleep on a comfortable mattress, and start your day with a complementary cup of coffee. Get a workout in the gym, hang out at the rooftop or walk around downtown. Being in the heart of downtown, the opportunities and activities are endless! To end the night, relax with a glass of wine and watch a movie on Hulu or Disney plus! Don't wait! Book your stay with us today!

Walking Bridge, Putt Putt House
NEW LISTING: Welcome to our walking bridge home on Pearl St. We have a hot tub, putt putt, and all the fun you can think of in one home. Steps away from restaurants, shopping, and bars, as well as the walking bridge to Louisville. This home is closer to the fun in Louisville than most neighborhoods in Louisville itself. Go out or stay in, you're guaranteed to have a great time in this newly renovated gem. We have high quality mattresses, and smart TV's in both bedrooms and the living room.

Captain's Cabin: Bourbon Trail, History & Romance
Your own log cabin on a wooded hillside with gourmet breakfast served to your door (on weekends)! It's been the location for 5 movies, including Lifetime! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife by the lake, creek or from back porch swings. Comfy bed, luxury sheets, high-speed internet, bluetooth stereo and special touches make your stay magical! Ask for Cooking With Bourbon Experience.

Private Parking in GTownWalk to Coffee,Shops,Bars!
Shotgun Rye is ready to host your stay in Louisville! Located close to everything cool in Germantown and Highlands area! People visit for Bourbon Tours, Ky Derby, Conventions, Expo Ctr, UL graduations and sporting events, live music and so much more! Completely remodeled with all the modern conveniences & a comfortable, casual touch. But with so much to see and do in Louisville you’ll load up your itinerary with unforgettable experiences. Great location walk to bars, restaurants and shopping!

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.

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.

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.

"The Brook" - Louisville
Enjoy a stay at this spacious, beautifully decorated ranch home in East Louisville. Blending organic modern decor and intentional functionality, you will feel relaxed and right at home. The home is nestled in a quiet neighborhood and yet only 1 mile from the interstate - conveniently located, a drive anywhere isn't far. Bring your crew to town to experience a day at the horse track, a bourbon tour, or a Kentucky family getaway!

Hidden GEM, newly furnished in a safe, great area
Our “unit” is a great place to stay. Absolutely wonderful neighborhood with beautiful historic setting, cozy, safe and quiet. Short walking distance to many restaurants, shops, coffee houses. Majestic trees line properties and homes. Downtown & NULU 4 miles. Churchill Downs 10 miles, University of Louisville is 13 miles away. Golf & swim center .25 miles this. property is duplex. Very separate accommodations! Private!
Popular amenities for outdoor seating rentals in St. Matthews
House rentals with outdoor seating

Newly Updated: Spacious Suite/Private Entry

Cozy Home w/ Fully Fenced Yard

Peppermint Cottage Norton Commons w Breakfast

Fall Haven - King Beds, Hot Tub

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

Crescent Hill near downtown

Bourbon Trail Spacious Backyard NEW HotTub Grill!

3 bedroom Crescent Hill cottage
Apartment rentals with outdoor seating

4th Street Suites - Comfortable King Bed Suite

★ Victorian Louisville ★ Beautiful 1200 sqft Apt

Urban Bourbon Farm Loft

Lucky Horseshoe

Falls City Loft - Free parking!

Downtown Luxury 1BR Apt near Louisville KY

Renovated Riverfront Apartment with Elevated Deck

Dreamy Designer-Curated Shoppable Retreat
Apartment rentals with outdoor seating

Luxe PLACE Apt in Lucky 13 Duplex w/ Free Parking

Cherokee Park / Highlands Charm

Lovely 3BR/1BA PRIME Location!

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
When is the best time to visit St. Matthews?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $204 SGD | $208 SGD | $247 SGD | $291 SGD | $389 SGD | $218 SGD | $226 SGD | $192 SGD | $284 SGD | $253 SGD | $217 SGD | $227 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 $52 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 a fireplace St. Matthews
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- Rentals with a firepit St. Matthews
- Rentals with outdoor seating Jefferson County
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- Rentals with outdoor seating United States
- Buffalo Trace Distillery
- Kentucky Kingdom & Hurricane Bay
- Kentucky Derby Museum
- Valhalla Golf Club
- Muhammad Ali Center
- Angel's Envy Distillery
- Louisville Slugger Field
- Heritage Hill Golf Club
- Charlestown State Park
- Louisville Slugger Museum & Factory
- Turtle Run Winery
- Falls of the Ohio State Park
- Big Four Bridge
- Kentucky Science Center
- Waterfront Park
- Hurstbourne Country Club
- River Run Family Water Park
- Big Spring Country Club
- Frazier History Museum
- Evan Williams Bourbon Experience
- Rising Sons Home Farm Winery
- Bruners Farm and Winery
- McIntyre's Winery
- Lovers Leap Vineyards and Winer




