
Holiday rentals with outdoor seating in Middletown
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Middletown
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
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Popular amenities for Middletown outdoor seating rentals
Holiday House Rentals with Outdoor Seating

NEW Pet Friendly, Horse Country, Bourbon, Downtown
My family had a great stay at this beautifully furnished home. It is centrally located within the pristine Norton Commons community, and it is close to many shops and restaurants. Great place to make home base for a trip to Louisville!

Quiet Neighborhood Home With Outstanding Location
A great little shotgun style house. Kitchen is well stocked with cooking basics. But there were no bathroom toiletries. A nice comfortable little place. Very quiet neighborhood.

Briar Creek Cottage
Great place to stay. Really well done. They have everything you need. Loved the kitchen and added amenities. Special thanks for the popcorn so we could watch our show Friday night. Worth every penny. Quiet and private yet close to everything you need. Best spot we've stayed at yet. Thanks for making my graduation weekend that much better.

Luxury home in Heart of Germantown!
A lovely, quiet oasis in Louisville. It's a spacious home with lots of character, private and charming, Courtney is at the ready if you need her! We fell in love with the neighborhood, which is worth exploring on foot for the randomly placed restaurants, shops, bakeries, and bars. Look for the wonderful murals everywhere. A terrific, unique Airbnb!

Entire House in Middletown - Trailers/RVs access
My friends and I were traveling to play a well-known golf course in the area, and we couldn't have found a better place to stay. The course was right down the street. There were plenty of restaurants, gas stations, and grocery stores around the corner. The house was exactly as described, and the host, Van, was terrific. He provided detailed information before our arrival and promptly responded to any questions we had. I would highly recommend this location for anyone visiting the area in the future.

Safe, comfortable, & convenient!
My Family and I 7 of us loved the location. Minutes from shopping, interstate, food, large enough yard to enjoy catch or just sitting together. Everything was clean and as described. The only thing I personally would focus on a bit more is yard maintenance, there wasn't anything crazy just some cleanup and trimming. Rob was a great host overall and had I needed anything I'm sure he would have gladly assisted however he could. I will book here again the next time I'm in the Louisville area!

502 House @ Progress Park w/ Game Room
Every year the grounds get more mature and beautiful!! The owners are always such a pleasure to interact with and the thought put into all the wonderful outdoor activities are remarkable! We do a large family glamping trip yearly, something we always look forward to!

Atoka Farms
If you are considering booking this home, don't think twice! It is a beautiful home and property, photos don't do it justice, and Kevin is so kind and helpful! He truly has thought of everything and does everything he can to help his guests feel welcome and relaxed! You can tell he cares very much about you having a great stay! I came with friends for a birthday weekend and we all left feeling so rested, exactly what Moms need on a weekend getaway! My expectations were exceeded in every way, this place is a gem and I hope to come back someday! Thank you so much Kevin!
Apartment rentals with outdoor seating

Lucky Horseshoe
Barbara was such an amazing host! We truly enjoyed our time and we're so happy we stayed with Barbara. She was so kind and very accommodating. The house is so charming, and the location is ideal of you're going to Churchill Downs, but also a great halfway point between downtown and the airport. Highly recommend!

Falls City Loft - Free parking!
Very comfortable king size bed and spacious kitchen. Great response time and communication from the host Justin. You will hear city sounds and some neighboring loft sounds but still feels private and safe! Would recommend to folks who are ok with carrying personal items a bit of a distance through hallways. Overall the loft was clean and comfortable and we loved the high ceilings!

Haus on Speed, charming 2nd floor apartment
Bethany's place was so cute! We loved sitting on the chaise to have our morning coffee, looking out at the magnolia tree across the way. The bed was very comfortable, and the blackout curtains were very effective! We slept well. We appreciated all the little touches- the local recommendations (we enjoyed walking to and around Cherokee park), the tea and espresso provided, the shower products- everything was thoughtful and comfortable and made our stay relaxing. We would be happy to stay again!

Stylish Urban Apt: King Bed, Gym, Pool & Hot Tub!
We had a great stay and the unit was exactly as described. Not having been to Louisville before, I tried finding something downtown that was walkable to lots of places. Turns out we needed to drive most places anyway, which made the parking garage less worth the hassle. But that's no reflection on this place. It was clean and adorable and made for a very pleasant stay!

Renovated Riverfront Apartment with Elevated Deck
Absolutely beautiful 2nd floor unit. We enjoyed sitting on the balcony, catching some views and rays. Loved having 2 bathrooms, laundry and a full kitchen. Easy parking spot behind or on a quiet street in front for quick access. Safe and peaceful area but not far from all the fun you could want. Very responsive host communication. We would stay here again without question when we make it back to the area.

Classy Urban Condo with Great Views
Super cozy apartment with all the vibes of an old building without the draft. Also has a lovely deck to sit on and drink your morning coffee.

Dreamy, Designer-Curated Shoppable Retreat
Jaclyn’s place was the perfect, dreamiest stay in a very walkable area! The decor originally drew us in (I mean how could it not — it’s absolutely gorgeous) but the amenities, convenience and Jaclyn’s prompt communication were the cherries on top. Would highly recommend her place if you’re looking for the coziest home away from home. Her guidebook with recommendations was amazing. We tried many of her suggestions and she was spot on with all of them!

Spacious & Artsy Highlands 3 Bedroom for Up to 6
Ann’s place was perfect for our girls weekend but would also be a great space for a family. Ann’s communication was great prior to and during our stay. All directions were clear. Would definitely recommend this place for someone looking for a quiet, peaceful stay in a residential neighborhood.
Condo rentals with outdoor seating

Your Kentucky Home Away From Home
Beautiful place easy check in and check out. Even though I always bring my own items if there is anything you may have forgotten or needed Katie had it there available for your use. I have family in the area and this will definitely be my go to place every time I return

Downtown Apt in NuLu | King Bed w/ parking
We’ve stayed here a number of times and it is consistently great! Just what you need for a trip to Louisville. Bed is comfy. Plenty of space. Easy to cook in the kitchen. Sophia is easy to communicate with and quick to respond. We love the NULU area. Check out Nouvelle next door when you are sick of bourbon. 🍷

Swanky 2 LEVEL CONDO WALK TO Everything Highlands!
We had an amazing stay at Matt's condo—it was cozy, well-stocked, and instantly felt like home. The guidebook provided was incredibly detailed and helpful, offering clear instructions and great local recommendations. The location is ideal, within walking distance to restaurants, bars, and breweries, and just a short drive to downtown or Churchill Downs. The condo itself is super comfortable with plenty of in-house entertainment options including video and board games, streaming services, disco lights, and fast Wi-Fi. Matt was an exceptional host—attentive, communicative from the start, and very accommodating. This place truly deserves five stars, and I’d happily stay here again on my next visit!

Hidden GEM, newly furnished in a safe, great area
Karen’s place was great! Very clean and had everything we would need. Very cute and comfortable. Would definitely stay again!

The Old Fashioned~Luxury 1BR~Stay Nulu Marketplace
Great stay!! Great location!!

Large Townhouse, Walk to All! King beds, 2.5 baths
Nice safe place for the value. Wasn’t a fan of the parking with a large SUV and current remodeling but it was safe and clean. The living area was spacious and comfortable. Rooms were clean.

Luxury Apartment/Near Louisville/EV Charger
Love the location, close to all the interstates. was very pleased with the host. got back to me within 10 minutes every time I had questions related to check in or travel didn’t have any issues while I was staying at the location. Very comfortable, quiet and peaceful. Was very pleased with all the amenities in the comfort of the beds in the TVs in every room, which was a very major plus in making my decision to stay with Toni. Would highly recommend stay with to anybody?

Downtown Condo | Private 1 CAR Garage & Balcony
Staying at this Airbnb was absolutely worth the price. The place was clean and conveniently located near plenty of great restaurants and bars. The host was very responsive, keeping us updated and giving helpful heads-ups about the unit. I would definitely recommend staying here!
Quick stats about holiday rentals with outdoor seating in Middletown
Total rentals
20 properties
Nightly prices starting at
$134 NZD before taxes and fees
Total number of reviews
640 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Destinations to explore
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- Buffalo Trace Distillery
- Kentucky Kingdom & Hurricane Bay
- Big Four Bridge
- Louisville Slugger Field
- Kentucky Derby Museum
- Louisville Slugger Museum & Factory
- Valhalla Golf Club
- Anderson Dean Community Park
- Muhammad Ali Center
- Angel's Envy Distillery
- Heritage Hill Golf Club
- Charlestown State Park
- Waterfront Park
- River Run Family Water Park
- Evan Williams Bourbon Experience
- Turtle Run Winery
- Kentucky Science Center
- Hurstbourne Country Club
- Frazier History Museum
- Falls of the Ohio State Park
- Big Spring Country Club