
Holiday rentals with outdoor seating in Middletown
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Middletown
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.

Home near the Highways
Comfortable, clean home in a quiet neighborhood Garage and driveway parking 3 Kings, 2 Queens, 2 Full beds, 2 Futons, 1 Loveseat Sleeper Sofa, 1 Couch Individual coffee makers in rooms with complementary coffee Peaceful front porch. Back and patio with gas & charcoal grills and green view Pet Friendly. Scroll down to "Other Things to Note" for more info. 2.5 miles to I-265. 3 miles to I-64. 20-30 minutes to most places in Louisville. 1 mi to a fuel, groceries, restaurants & banking

Clifton Loft Retreat – King Bed & Air Hockey!
Enjoy a peaceful stay in this stylish loft in the heart of the beautiful Clifton neighborhood! With the ability to sleep 6 comfortably, this space is perfect for groups and families looking to explore the 'Ville! You will be surrounded by restaurants, parks,and plenty of activities for everyone! Wake up to a cup of coffee before hitting the town for shopping, a bite to eat, or sightseeing! Come on back and have a drink on the balcony or take part in a game of air hockey! Book your stay today!

Downtown Chic Apt – King Bed, Gym, Pool & Hot Tub
This stylish and luxurious apartment is perfect for couples, families, and small groups! Upon entering the apartment, you'll be greeted by modern appliances and renovations, stylish decor, and everything you would need for your stay! Enjoy a peaceful night's sleep on a comfortable bed before venturing out to see everything Louisville has to offer, most of which is right at your doorstep!Don't want to venture out? You'd have a gym,rooftop, and even a golf simulator to enjoy! Book with us today

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!

"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!!

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.

Brakeman's Cottage
"All Aboard the Brakeman's Cottage! Experience the charm of this tiny house listed on the National Register of Historic Buildings in LaGrange, Kentucky. Nestled just feet from the train tracks in the heart of downtown, it offers a unique experience. Situated across from the train observation tower and within walking distance of the best restaurants and quaint shops, our newly remodeled property features private off-street parking. Step into history with modern comforts at Brakeman's

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.

Private Prospect Flat
Two bedroom apartment located on picturesque Covered Bridge Road in Prospect, KY. There is a separate entrance with plenty of parking. Beautiful views of Kentucky landscape from every window. Our property is four acres with a meandering stream, forest, and fields. There is a fully stocked kitchen including a dishwasher. The main bedroom includes a work space area and two closets. Feel free to grab a few eggs for breakfast if there are eggs in the nesting boxes.

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 Middletown
House rentals with outdoor seating

Charming 4 Bedroom classic home bourbon trail!

Cozy Home w/ Fully Fenced Yard

Lil Blue-Cheerful, fully renovated & updated home

Romance country getaway with hot tub

2 br home, walking distance to much entertainment

Quaint Highland's Bungalow

Parkside Pad - Iroquois Park

Cheerful, centrally located 2 bedroom shotgun home
Apartment rentals with outdoor seating

★ Victorian Louisville ★ Beautiful 1200 sqft Apt

Urban Bourbon Farm Loft

Lucky Horseshoe

Apartment on Frankfort Ave: Walkout Basement

Falls City Loft - Free parking!

Downtown Luxury 1BR Apt near Louisville KY

Haus on Speed, charming 2nd floor apartment

Renovated Riverfront Apartment with Elevated Deck
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

The Greatest penthouse in the heart of city

Charming Penthouse/Rooftop Patio/Downtown
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $181 SGD | $172 SGD | $178 SGD | $290 SGD | $290 SGD | $187 SGD | $249 SGD | $265 SGD | $269 SGD | $190 SGD | $181 SGD | $230 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 Middletown

Total holiday rentals
Explore 20 holiday rentals in Middletown

Nightly prices starting at
Middletown holiday rentals start at $104 SGD per night before taxes and fees

Verified guest reviews
Over 630 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Middletown holiday rentals include wifi access

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

4.8 Average rating
Middletown stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Western North Carolina Holiday rentals
- Chicago Holiday rentals
- Nashville Holiday rentals
- Gatlinburg Holiday rentals
- Pigeon Forge Holiday rentals
- Downtown Chicago Holiday rentals
- Indianapolis Holiday rentals
- Asheville Holiday rentals
- Southern Indiana Holiday rentals
- St. Louis Holiday rentals
- Columbus Holiday rentals
- Louisville Holiday rentals
- Family-friendly rentals Middletown
- Rentals with a patio Middletown
- House rentals Middletown
- Rentals with a fireplace Middletown
- Rentals with a washing machine and dryer Middletown
- Pet-friendly rentals Middletown
- Rentals with outdoor seating Jefferson County
- Rentals with outdoor seating Kentucky
- 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
- Anderson Dean Community Park
- 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
- Equus Run Vineyards




