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

Total holiday rentals
Explore 20 holiday rentals in Middletown

Nightly prices starting at
Middletown holiday rentals start at $141 SGD per night before taxes and fees

Verified guest reviews
Over 310 verified reviews to help you choose

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

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!
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 spacesWalkabilityQuiet

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
WalkabilityPetsIndoor spaces

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.
PetsOutdoor spacesCondition

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.
Outdoor spacesPetsQuiet

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.
PetsOutdoor spacesIndoor spaces

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.
WalkabilityOutdoor spacesLayout

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 spacesFamily

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.
PetsWalkabilityValue

...Happy Trails House in Derby City
4 bedroom, 2 full baths, 1 half bath, ( bedrooms on 2nd floor, none on 1st floor ). Our home is on a dead end street steps away to a walking trail, fenced yard, 2 patios, charcoal grill. Only 15 to 20 min. drive to Downtown, Churchill Downs, Hospitals, Airport, close to major highways. Near restaurants, shopping centers, grocery, liquor store etc. pets welcome with $10 fee per pet per night. Washer/dryer and dishwasher
PetsOutdoor spacesValue

Highlands Lower Level Studio Guest Suite
Private, well-lit, entrance is in rear of home. The space is approx. 600sq. ft. There is a gas fireplace, 42" HD TV w/Netflix & Amazon Prime. Kitchen has Keurig coffee maker, convection oven, inferred glass top burner, microwave, refrigerator/freezer w/ice, washer/dryer& a large marble shower, with heated floors in the shower room. Also space equipped w/ Medify air purifier w/H13 true Hepa medical grade filter.
Outdoor spacesWalkabilityParking

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!
PetsWalkabilityGetting around

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.
WalkabilityPetsBiking
Popular amenities for Middletown pet-friendly home rentals
Pet-friendly house rentals

Colonel Lou Lou's
Outdoor spacesPetsAccess

Best of the Ville’s Modernised
Outdoor spacesWalkabilityLayout

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

The Caldwell Highlands/Germantown
Outdoor spacesWalkabilityNearby

The Green House in Downtown
Outdoor spacesWalkabilityBathroom

Waterfront Red Ruby ping pong shuffle board
PetsWalkabilityCheck-in

Lovely home minutes from Louisville
Outdoor spacesPetsCleanliness

It’s very welcoming
PetsOutdoor spacesBack garden
Pet-friendly home rentals with a pool

Cozy Neighborhood Home - 10 min to Louisville!
WalkabilityPetsQuiet

Lakeside Haven Cottage 4, Lake View, Hot Tub, Pool
Outdoor spacesPetsIndoor spaces

10 min to Lou~Huge Hot Tub~Fenced Backyard~Games
Outdoor spacesWifiGetting around

#18 Kentucky Sunrise - Lakefront Home with spacuio
Outdoor spacesWalkabilityAccess

Lake Livin' & Bourbon Sippin'
PetsWalkabilityBiking

The Getaway!
PetsCleanlinessPool

Urban Lakeside 3BR Retreat Private Pool
Outdoor spacesSleep qualityFamily

Happy Goose Hollow
PetsOutdoor spacesGetting around
Private, pet-friendly home rentals

The Writer’s Den
PetsOutdoor spacesWifi

Trendy Tiny Home w/ King Bed Loft
PetsWalkabilityLaundry

Cute and Cozy Private Studio Getaway in Louisville
Outdoor spacesPetsLayout

The Cottage at StoneLedge 2 bedroom/1bath
Outdoor spacesWalkabilityCheck-in

NEW! Cozy, Private Highlands Studio
PetsWalkabilityAir conditioning

Thompson Hideaway
Outdoor spacesPetsComfort

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

This old Kentucky home - Middletown/Derby/Bourbon
Outdoor spacesPetsParking
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $184 SGD | $178 SGD | $177 SGD | $209 SGD | $214 SGD | $178 SGD | $198 SGD | $183 SGD | $235 SGD | $209 SGD | $178 SGD | $191 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 |
Destinations to explore
- Nashville Holiday rentals
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- Louisville Holiday rentals
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- Knoxville Holiday rentals
- Kentucky Exposition Center
- Buffalo Trace Distillery
- Kentucky Kingdom & Hurricane Bay
- Churchill Downs
- Kentucky Derby Museum
- Louisville Slugger Field
- Waterfront Park
- University of Louisville
- Kentucky International Convention Center
- Louisville Slugger Museum & Factory
- Jefferson Memorial Forest
- Muhammad Ali Center
- Falls of the Ohio State Park
- Castle & Key Distillery
- James B Beam Distilling
- Angel's Envy Distillery
- Big Four Bridge
- Bernheim Arboretum and Research Forest
- Bardstown Bourbon Company
- Frazier History Museum
- Marengo Cave National Landmark
- Cherokee Park
- Four Roses Distillery Llc
- Kentucky Science Center





