
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 $152 CAD 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 and kid-friendly amenities

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!
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.

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.

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

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.

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.

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.

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.

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.

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.

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!

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.

Thompson Hideaway
Our cozy home is tucked back off the road, located directly behind the Mellwood Art Center. The neighborhood has a large selection of restaurants and one of the best bars for live music in the city Mellwood Tavern. Nulu, Downtown and the Highlands are all very close by. This home is a good option for couples, families, or a trip with friends. Great for a Travel Nurse with a dog
Popular amenities for Middletown pet-friendly home rentals
Pet-friendly house rentals

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

Cabin in the Woods on Lake Close to Louisville Ky

Nulu | Bourbon District | 4 Bedroom | Fire Pit

Luxe Waterfront w/Hot Tub Cinema Sauna Pet Views

The Mashbill | Boutique Bourbon Retreat | Walkable

Comfortable sleek home bourbon trail

Parkside Pad - Iroquois Park

Kentucky Hug: A Modern Shotgun for Bourbon Elites
Pet-friendly home rentals with a pool

3.7 Acre Estate w/ Heated Pool, 5 Kings-2 Game Rms

The Getaway!

Entire Home with Indoor Spa & Pool

Pet Friendly, Pool, Shops, Downtown, Bourbon, Golf

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

Happy Goose Hollow

Lake Livin' & Bourbon Sippin'

10 min to Lou~Huge Hot Tub~Fenced Backyard~Games
Private, pet-friendly home rentals

Louisville Getaway

NEW! Cozy, Private Highlands Studio

Highlands Lower Level Studio Guest Suite

Crestwood Louisville | Hot Tub | Bourbon Trail

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

Swanky Fully Equipped St. Matthews Apartment

This old Kentucky home - Middletown/Derby/Bourbon

Unique Downtown Studio with an Industrial Vibe
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $198 CAD | $192 CAD | $190 CAD | $225 CAD | $230 CAD | $192 CAD | $214 CAD | $197 CAD | $254 CAD | $225 CAD | $192 CAD | $205 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 |
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- Kentucky Exposition Center
- Buffalo Trace Distillery
- Kentucky Kingdom & Hurricane Bay
- Kentucky Derby Museum
- Churchill Downs
- Louisville Slugger Field
- Waterfront Park
- Kentucky International Convention Center
- University of Louisville
- Louisville Slugger Museum & Factory
- Muhammad Ali Center
- Jefferson Memorial Forest
- Falls of the Ohio State Park
- Castle & Key Distillery
- James B Beam Distilling
- Angel's Envy Distillery
- Marengo Cave National Landmark
- Bernheim Arboretum and Research Forest
- Bardstown Bourbon Company
- Frazier History Museum
- Big Four Bridge
- Four Roses Distillery Llc
- Cherokee Park
- Kentucky Science Center





