
Pet-friendly vacation rentals in Middletown
Find and book unique pet-friendly homes on Airbnb
Quick stats about vacation rentals that are pet-friendly in Middletown

Total vacation rentals
Explore 20 vacation rentals in Middletown

Nightly prices starting at
Middletown vacation rentals start at ﺩ.ﺇ 404 per night before taxes and fees

Verified guest reviews
Over 310 verified reviews to help you choose

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

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Middletown vacation rentals include wi-fi 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!
Top-rated pet-friendly home rentals in Middletown
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

Cozy cottage, pets, private, convenient, parking
This secluded mid century cottage is just minutes to downtown and other amenities. Located in Clifton Heights, this three bedroom, bath and a half home is inviting and cozy. Located 6 miles from two large malls, 1 mile from the new walking bridge over the Ohio River, and one and a half miles to unique shopping, nightlife and restaurants. Also, the home is only a short distance to I 71 and I 64. This makes everything convenient and accessible from this private location. The home has vintage charm with renovations for convenience. Each Bedroom has a flatscreen TV as well as a 56 inch flatscreen in the living room. There is a private front yard with gardens, seating, and a grill. There are 6-7 spaces for off street parking. The eat-in kitchen seats six, with a double oven microwave, full-size fridge, gas stove and a dishwasher. There is service for 12 including Louisville Hadley Pottery.
Outdoor spacesWalkabilityFamily

Cozy Neighborhood Home - 10 min to Louisville!
Relax just 10 minutes from downtown Louisville at this beautiful patio home in a newly built community. Perfect for a weekend trip, business travelers, those with pets, travel nurses, and others! Quick, easy access to River City via I-65 or East End Bridge from a quiet, charming neighborhood. Equipped with an office space and fast fiber optic wifi for those working remotely. Grocery and restaurant options just 0.5 miles away. Also enjoy the neighborhood’s paved walking trail with a lake view.
Outdoor spacesPetsFamily

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
WalkabilityPetsHospitality

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.
Outdoor spacesPetsLaundry

Hide away close to everything
Recently remodeled in law suite. We just upgraded the bed to a queen size. Very private, detached garage getaway. A cozy sitting area 60" CableTV with HBO SHOWTIME and STARZ. Wet bar with fridge, ice maker, coffee maker, microwave, hot plate, dishes and some cookware. Private bath has shower and a walk in closet. This private apt. is above the garage. Outside has fenced in yard for your furry friend, outdoor fire pit and sitting area. Close to the interstate and minutes from downtown.
PetsWalkabilityNearby

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.
Outdoor spacesWalkabilityKitchen

Eclectic/Modern 1 BR in Clifton!
Updated 1 bedroom/1 bathroom stylish retreat right in the heart of the Historic Clifton neighborhood. Clifton is directly off Frankfort Avenue near the Highlands, Nulu, St Mathews, and Old Louisville neighborhoods. This 600 sq ft charming shotgun home was built in the 1900’s and it has a ton of character and “old home” charm, while still having updated features throughout. This home is very close to many restaurants and shops! You can walk, drive, or bike to Frankfort Ave.
WalkabilityPetsHeating

My Old Kentucky Dome
An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.
WalkabilityOutdoor spacesAccess

The Point at Story and Frankfort Avenue
The Point is a spacious and completely renovated one bedroom (king) apartment. You will absolutely love the huge sectional couch while watching your favorite shows on the 65" smart TV. Unit very close to downtown with tons of options for local restaurants, breweries, bourbon tours and bars. Building is located in the heart of Butchertown right down the street from the new Botanical gardens, Nulu, walking bridge and soccer stadium.
PetsWalkabilityComfort

Bourbon Trail*Tesla EV charger* 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!
PetsWalkabilityHeating

One Room Apartment with Private Off Street Parking
Room is a stand alone efficiency with a kitchenette, blackout curtains, and reclining queen bed. It has one designated parking space and seperate entrance. Unit has private bath and walk in closet, and kitchenete. Also has refeigerator, coffee maker, work desk microwave, 42" smart tv, Ninja airfryer oven, and couch. Private porch with table and chairs. Close/secure single parking space.
WalkabilityPetsCleanliness

HIghlands Modern Get Away
Ideal, quiet place in the highlands. You have the apartment over the garage. You'll have a place all to yourself with most the amenities of your own home. Studio apartment with a balcony if you decide to hang out and relax for the evening. There is a cook top, but no oven in the kitchen. Park in the driveway in front of the garage. Pets are welcome, plz add them when booking.
WalkabilityPetsComfort
Popular amenities for Middletown pet-friendly home rentals
Pet-friendly house rentals

3BR Home Near Zoo & Fairgrounds – Family-Friendly!
WalkabilityOutdoor spacesValue

Waterfront Red Ruby ping pong shuffle board
WalkabilityOutdoor spacesBathroom

Lilly's Pad
PetsOutdoor spacesHospitality

Comfortable sleek home bourbon trail
WalkabilityPetsValue

Quaint Highland's Bungalow
Outdoor spacesWalkabilityQuiet

The Green House in Downtown
WalkabilityPetsParking

The Caldwell Highlands/Germantown
WalkabilityOutdoor spacesBackyard

Thompson Hideaway
PetsWalkabilityAir conditioning
Pet-friendly home rentals with a pool

The Getaway!
PetsComfortGetting around

Lakeside Haven Cottage 4, Lake View, Hot Tub, Pool
WalkabilityOutdoor spacesQuiet

Wildflower Cottage on Taylorsville Lake
NearbyGrillFamily

Happy Goose Hollow
Outdoor spacesPetsLong stay

NEW Family Resort Home with Saltwater Pool & Games
PetsOutdoor spacesFamily

Urban Lakeside 3BR Retreat Private Pool
Outdoor spacesBackyardDecor

Lake Livin' & Bourbon Sippin'
Outdoor spacesWalkabilityBackyard

Whiskey River Lake Retreat
WalkabilityPetsNearby
Private, pet-friendly home rentals

Riverfront Cottage
PetsOutdoor spacesCleanliness

Louisville Getaway
PetsWalkabilityNearby

Cottage Retreat at Tiwazzen Farm
PetsWalkabilityBathroom

Crestwood Louisville | Hot Tub | Bourbon Trail
Outdoor spacesPetsValue

Charming Highlands apartment
WalkabilityPetsKitchen

Safe, comfortable, convenient, hot tub, fire pit!
Outdoor spacesLayoutTV

SuperHost ~ Beautiful NEW Modern Condo w/ 75" TV
TVQuietAccuracy

This old Kentucky home - Middletown/Derby/Bourbon
Outdoor spacesPetsValue
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 529 | ﺩ.ﺇ 510 | ﺩ.ﺇ 507 | ﺩ.ﺇ 599 | ﺩ.ﺇ 613 | ﺩ.ﺇ 510 | ﺩ.ﺇ 569 | ﺩ.ﺇ 525 | ﺩ.ﺇ 676 | ﺩ.ﺇ 599 | ﺩ.ﺇ 510 | ﺩ.ﺇ 547 |
| 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 |
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- Kentucky Exposition Center
- Buffalo Trace Distillery
- Kentucky Kingdom & Hurricane Bay
- Kentucky Derby Museum
- Louisville Slugger Field
- Churchill Downs
- Waterfront Park
- University of Louisville
- Kentucky International Convention Center
- Louisville Slugger Museum & Factory
- Jefferson Memorial Forest
- Falls of the Ohio State Park
- Muhammad Ali Center
- Castle & Key Distillery
- Angel's Envy Distillery
- James B Beam Distilling
- Big Four Bridge
- Bernheim Arboretum and Research Forest
- Frazier History Museum
- Marengo Cave National Landmark
- Bardstown Bourbon Company
- Four Roses Distillery Llc
- Cherokee Park
- Kentucky Science Center





