
Holiday rentals with a patio in Middletown
Find and book unique rentals with patio on Airbnb
Top-rated rentals with patio in Middletown
Guests agree: these rentals with a patio 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.

Little Luxury in Jeffersonville
VisitJeff & Louisville and stay in this newly renovated home! 1 Bed/1 bath. Fenced in patio area & private driveway. Walk to parks, dining & shopping in downtown Jeffersonville. High ceilings, quaint space, modern ammenities! New chef's kitchen, dining table, island seating, queen size bed, comfy couch, LUXURY bathroom w stand alone soaker tub, shower & plenty of vanity space! Perfect for 2 guests (and or a child ) Washer and dryer. We live near by & have another Air B N B across the street!

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.

Stella Airstream at Progress Park in Derby City
This gorgeous silver bullet is our Stella Airstream, lovingly named after Wally Byam's wife Stella! She is a 1983 Airstream Classic. She's loaded with all the modern amenities! Stella can sleep 6 comfortably with 2 king beds and 2 bunk beds. There's a private toilet/shower with 2 add'l nearby. You'll have a kitchen & covered patio with grill & firepit. There are 11 total units on site. 2 houses, 8 airstreams & a bunk house. *DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

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.

"Call Me Old-Fashioned"in Derby & Bourbon Country!
Welcome to "Call Me Old-Fashioned" - a unique spin on Bourbon w/ a mix of new & vintage amenities! Located in a QUIET & SAFE neighborhood, this family-friendly home is located close to Downtown Louisville & Churchill Downs (18 min), Expo Center & airport (15 min). Bardstown, the Bourbon capitol, is 35 min away. We are also 5 min from Parklands @ Floyds Fork park system - home to 60 miles of hiking, biking & paddling trails & a big playground. Come make yourself at home in our cozy KY home!

12 Guest/Top Area /Families/Park
Welcome to our Family Airbnb 1- Great Location in residential neighborhood 2- 20 Min to Kentucky Derby Museum 3 - 20 Min to Louisville Mega Caverns 4- 15 Min Evan William Bourbon 5- 20 Min Churchill Down 6- Designed for 2 guests (3 Queen Bed, 1 double Bunk bed, 1 Queen Air Mattress) 7- Free Parking (2 Cars Inside and 2 Cars Outside) 8- Fully Equipped Kitchen 9- Fast Wi-Fi 10- Quiet and Safe Area 11- Private Patio 12-24/7 Available Host 13- 2 Smart TVs 14- Laundry In Unit

The Squirrel's Nest - 3 bedroom house with hot tub
Welcome to the Squirrel's Nest where you can relax and enjoy the country! Only 5 mins from historic downtown LaGrange, 20 mins from Louisville-home of the Kentucky Derby and next door is the FRP-LaGrange Quarry water park. The back patio overlooks the woods where you can watch deer, turkey & the squirrels play! The master bedroom has a queen bed, the second & third bedrooms have full beds. The kitchen is fully equipped. No pets. No parties, no events.

Beach Vibes 2 mile to Whiskey Row Bourbon City
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 Caldwell Highlands/Germantown
Welcome to The Caldwell, a Germantown/Highland area home that includes three bedrooms, one and half bathrooms and sleeps up to five people. The home is within walking distance of several restaurants, bars, retail and vintage stores, and entertainment venues including the Germantown Gables, Logan Street Market and Old Forester’s Paristown Hall. The home features a covered deck, a fenced-in yard as well as home gym.

Bourbon Trail*Tesla EV charging* HOT TUB
Welcome to the Bourbon Bungalow, a tastefully restored farmhouse on the famous Kentucky Bourbon Trail. This southern retreat is on the outskirts of Louisville in the quaint city of Pewee Valley. A short drive to some of the states most sought after locations such as Churchill Downs, bourbon distilleries, horse parks, caves, Shelbyville, Bardstown, & more! The Bourbon trail is waiting for you!

For the ones who serve
We decorated and dedicated this place in honor of my father who served in WW2 as a Marine. He passed March of 2020. We have all type of military things along with other unique pieces. We plan on always coming up with more things to change it around. This is a part of a duplex which sits on the property with our wedding venue. Check out our guide book for local attractions and mileage
Popular amenities for rentals with patio in Middletown
Flat rentals with a patio

Cozy Studio in Brooks

1 Bedroom Apt in Highlands Home w/private patio

3 mi to Derby - Brick Alley Hütte

B On Main Unit 1

Falls City Loft - Free parking!

Downtown Luxury 1BR Apt near Louisville KY

Stylish DT Apt • King Bed, Gym, Pool + Hot Tub

Dreamy Historic Designer Curated Apartment
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Luxury Waterside Retreat with Geo Dome+Fire Table

Cozy Home w/ Fully Fenced Yard

Luxury 3 bedroom home 7 mins away KY Fair Expo

BRAND NEW, Jeff, IN, Cottage, Trifecta Way

The Rickhouse ~ NULU ~ Bourbon Enthusiast’s Oasis!

2BR 4Guest Highlands w/ Parking, Office, PacknPlay

Comfortable sleek home bourbon trail

Louisville Luxury: Expo Center, Hot Tub, Bourbon
Apartment rentals with a patio

Perfect Location! Huge Space in Walkable Highlands

Bitters Suite-New on Bourbon Trail! BRAND NEW!

Cherokee Park / Highlands Charm

2BR | 2BA - Downtown Apt in NuLu w Private Parking

The Bunker

2 bedroom condo in Downtown Louisville

Entire Game Loft for 16, Walk to Nulu

BEST View of Louisville
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $178 SGD | $169 SGD | $176 SGD | $298 SGD | $289 SGD | $185 SGD | $245 SGD | $192 SGD | $257 SGD | $209 SGD | $176 SGD | $191 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 a patio in Middletown

Total holiday rentals
Explore 30 holiday rentals in Middletown

Nightly prices starting at
Middletown holiday rentals start at $103 SGD per night before taxes and fees

Verified guest reviews
Over 700 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
20 properties have a dedicated workspace

Wifi availability
30 of Middletown holiday rentals include wifi access

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

4.9 Average rating
Middletown stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with a patio Jefferson County
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- Rentals with a patio United States
- Buffalo Trace Distillery
- Kentucky Derby Museum
- Kentucky Exposition Center
- Kentucky Kingdom & Hurricane Bay
- Churchill Downs
- Valhalla Golf Club
- Louisville Slugger Museum & Factory
- Muhammad Ali Center
- Angel's Envy Distillery
- Louisville Slugger Field
- Big Four Bridge
- Falls of the Ohio State Park
- Kentucky Science Center
- Waterfront Park
- L&N Federal Credit Union Stadium
- James B Beam Distilling
- Evan Williams Bourbon Experience
- University of Louisville
- Four Roses Distillery Llc
- Kentucky International Convention Center
- Castle & Key Distillery
- Marengo Cave National Landmark
- Jefferson Memorial Forest
- Bernheim Arboretum and Research Forest




