
Vacation rentals with a patio in Middletown
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Top-rated patio rentals in Middletown
Guests agree: these patio rentals 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.

Peppermint Cottage Norton Commons w Breakfast
Step into Peppermint Cottage and find the perfect blend of convenience and charm! Just 20 minutes from SDF airport, Churchill Downs, and downtown Louisville's excitement, this trendy east end haven offers an irresistible walkable lifestyle. Stroll or bike to 18 mouth watering restaurants, 14 unique boutiques, and YMCA with pool. Enjoy lakeside fishing, Sunday farmers markets, summer concerts, parks and Friday food truck festivities. Your ideal Louisville adventure awaits at Peppermint Cottage!

"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.

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.

Modern stay overlooking downtown
Forget your worries in this Luxury spacious and serene space. Make yourself at home! Relax in the unique 1Bedroom Queen size bed with Restaurants and smoothie bar in building! you’ll be close to Restaurants alongside the Ohio river, Kfc Yum Center, Downtown Walking bridge , Deserts , bars , music and more! Great wifi, meeting rooms open 24/7 charging stations for your electric vehicle! Last but not least Beautiful overlook of downtown Louisville on charming rooftop patio!

Haus on Speed, charming 2nd floor apartment
Welcome to the Haus on Speed! Please note that if you have mobility issues, the apartment is on the 2nd floor and you will need to be able to climb about 20 carpeted steps. There are also 6 exterior steps when walking up from the sidewalk. Walk to anything from our charming 100+ year old Highlands home in one of Louisville's more vibrant & loved neighborhoods! This home is thoughtfully furnished to include all the comforts you could need during your stay.

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.

"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!

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.
Popular amenities for Middletown patio rentals
Apartment rentals with a patio

For the ones who serve

Cozy Studio in Brooks

4th Street Suites - Comfortable King Bed Suite

second floor 1 bedroom + office W/D & easy parking

Courtyard View w/ Free Wifi & In Unit Washer/Dryer

Falls City Loft - Free parking!

Downtown Luxury 1BR Apt near Louisville KY

Beach Vibe close to Museum Row
House rentals with a patio

Bright, fun, and colorful home

Camp Taylor Hideaway Close to Audubon Hospital

Highlands Bishop Cottage-Walkable

Parkside Pad - Iroquois Park

The Old McDonald Lane

Cute, Cozy, & Clean Home in Louisville

Cheerful, centrally located 2 bedroom shotgun home

Best of the Ville’s Modernised
Condo 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

Cozy Apartment-Whiskey Row Louisville - Sleeps 6

Butchertown Game Loft: Sleeps 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 | R2,375 ZAR | R2,255 ZAR | R2,341 ZAR | R3,964 ZAR | R3,844 ZAR | R2,460 ZAR | R3,263 ZAR | R2,563 ZAR | R3,417 ZAR | R2,494 ZAR | R2,204 ZAR | R2,392 ZAR |
| 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 a patio in Middletown

Total vacation rentals
Explore 40 vacation rentals in Middletown

Nightly prices starting at
Middletown vacation rentals start at R1,196 ZAR per night before taxes and fees

Verified guest reviews
Over 650 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Middletown vacation rentals include wi-fi 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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- 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
- 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




