
Vacation rentals with outdoor seating in Middletown
Find and book unique accommodations with outdoor seating on Airbnb
Top-rated accommodations with outdoor seating in Middletown
Guests agree: these accommodations 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.

The Germantown Loft * Privacy & Convenience *
Enjoy the private, newly-renovated top floor of an eccentric 2-story brick building in the heart of Louisville’s hip Germantown. Originally constructed in the 1800's and now furnished with life’s modern amenities, you’ll appreciate all this unique space offers while being centrally located between NULU, the Highlands, and Germantown’s most enjoyable hangouts. All within 5-minute walk: Logan Street Market, Atrium Brewing, Kaiju, Nachbar, Red Top Gourmet Hotdogs, Hammerheads, Full Stop, and more.

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

Bourbon Trail, Firepit
After a beautiful drive along a tree-lined-canopied road, you will find Mint Julep Villa, located on a private 1.3 acre lot and just one street over from the Ohio River. Mint Julep Villa, is tastefully decorated for you and your family to enjoy your stay in the Louisville and Prospect KY area. No matter if it's the Bourbon trails, the Kentucky Derby, the numerous concerts and the many other attractions to draw you to Kentucky, Mint Julep Villa will be a place you'd be attracted to as well.

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.

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.

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.

Newly Updated: Spacious Suite/Private Entry
My guest suite is close to restaurants, business parks, shopping and easy access to highways. Guests love this place because of the big trees, green space and private entrance. The patio is great for sipping morning coffee, reading or enjoying an evening beverage. Beautiful, quiet neighborhood is perfect for a walk/run. This spacious, comfortable suite is good for couples, solo adventurers, business travelers and small families.

"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!
Popular amenities for Middletown outdoor seating rentals
House rentals with outdoor seating

2BR Home Near Zoo & Fairgrounds – Family-Friendly!

Quiet Neighborhood Home With Outstanding Location

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

Its what's inside that counts!

Quaint Highland's Bungalow

Charming Shotgun Style Home, Great Location

Parkside Pad - Iroquois Park

The Green House in Downtown
Apartment rentals with outdoor seating

Urban Bourbon Farm Loft

Lucky Horseshoe

Apartment on Frankfort Ave: Walkout Basement

Deuward’s Den - In Historic Corydon, IN

Downtown Luxury 1BR Apt near Louisville KY

Renovated Riverfront Apartment with Elevated Deck

Dreamy Designer-Curated Shoppable Retreat

Spacious & Artsy Highlands 3 Bedroom for Up to 6
Condo rentals with outdoor seating

Luxury 1-Bed Oasis In Heart Of Highlands W/ Free P

Cherokee Park / Highlands Charm

Hidden GEM, newly furnished in a safe, great area

Large Townhouse, Walk to All! King beds, 2.5 baths

The Old Fashioned~Luxury 1BR~Stay Nulu Marketplace

Spacious Riverfront Condo Minutes from Downtown!

Downtown Condo | Private 1 CAR Garage & Balcony

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 | $194 CAD | $185 CAD | $192 CAD | $312 CAD | $312 CAD | $201 CAD | $206 CAD | $267 CAD | $280 CAD | $204 CAD | $194 CAD | $247 CAD | 
| 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 vacation rentals with outdoor seating in Middletown
 - Total vacation rentals- Explore 20 vacation rentals in Middletown 
 - Nightly prices starting at- Middletown vacation rentals start at $112 CAD per night before taxes and fees 
 - Verified guest reviews- Over 630 verified reviews to help you choose 
 - Family-friendly vacation rentals- 20 properties offer extra space and kid-friendly amenities 
 - Pet-friendly vacation rentals- Find 10 rentals that welcome pets 
 - Rentals with dedicated workspaces- 10 properties have a dedicated workspace 
 - Wifi availability- 20 of Middletown vacation 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! 
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- Rentals with a fireplace Middletown
- Rentals with a washer and dryer Middletown
- Family-friendly rentals Middletown
- Rentals with a patio Middletown
- House rentals 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
- Louisville Slugger Museum & Factory
- Charlestown State Park
- Turtle Run Winery
- Falls of the Ohio State Park
- Big Four Bridge
- Kentucky Science Center
- Waterfront Park
- River Run Family Water Park
- Frazier History Museum
- Big Spring Country Club
- Evan Williams Bourbon Experience
- Rising Sons Home Farm Winery
- Bruners Farm and Winery
- Equus Run Vineyards
- McIntyre's Winery
