Pet-friendly holiday rentals in Middletown

Guest house in New Lebanon

The exterior of the studio cottage is seen, featuring white siding and red shutters. A walkway leads to the entrance, bordered by vibrant flower pots. Plants are hanging from the front, and a grill area is visible in the background among greenery.

4.97 out of 5 average rating, 222 reviews

Cottage on a working market garden

Studio cottage with full bath and self-catering kitchen with pots and pans, etc., queen sized bed with fresh linens and towels provided. This cottage is on a working market garden. Maximum occupancy two adults. We do have a small bed that could be added to accommodate a small child about 6 years and under. WE WILL ACCEPT SOME PETS, BUT NOT ALL. We are one mile from grocery shopping. Local roads ideal for cycling. Thirteen miles west of Dayton. Price includes fresh flowers and vegetables from the garden during the season. One cat on the property. Cottage has ceiling fan and good air circulation and a window air-conditioner during the warmer months. There is a TV that streams Apple TV and Kanopy in the cottage, and excellent WIFI access. National Air Force Museum in Dayton is only 20 miles/ 30 minutes away. University of Dayton is 14 miles/ 20 minutes from the cottage. Dayton International Airport is 21 miles/ 26 minutes away. Your hosts are a hospitable couple who enjoy meeting new people. If no one else is booked after you, we can be more flexible with the check-out time.

4.92 out of 5 average rating, 177 reviews

A well-appointed bedroom features a spacious bed with textured bedding, surrounded by moody grey walls. Natural light is invited in through large windows, framed by vibrant curtains. An area rug adds warmth, while a wicker chair and minimalist decor enhance the inviting ambiance.

Home in Seminary Square

Cozy Hot Tub Escape, Walkable to Bars/Restaurants

A romantic getaway with vintage soul — complete with an exclusive, semi-private hot tub under the stars. This beautifully restored pre-1860 home pairs bold design and cozy comfort for the perfect couple’s escape. Sink into the plush king bed for a peaceful night’s sleep. The unique bathroom — with its luxurious finishes and historic charm — is a guest favorite. The shops, restaurants & bars of MainStrasse or Madison Ave are just a 10 min walk. Downtown Cincinnati is only a few mintues by car!

4.95 out of 5 average rating, 452 reviews

Guest house in Lebanon

Private carriage house on 3 acres!

New for 2024/2025... updated furniture with memory foam sleeper sofa, memory foam king and queen beds, additional twin mattress for floor for extra sleeping options. Outdoor conversation area! Bright and airy carriage house, located behind main house on 3 acres in Lebanon, Ohio. Close to downtown Lebanon, Springboro, Waynesville and short drive to Kings Island. -Kings Island 11 miles -Warren County Sports Park 7 miles -Roberts Center Wilmington 20 miles -Caesar Creek State Park 10 miles

4.96 out of 5 average rating, 161 reviews

The house features a white exterior with a distinctive red metal roof. A welcoming front porch is accessible through a covered entry, surrounded by lush greenery and mature trees, creating a serene setting. The windows are framed by traditional shutters, adding character to the structure.

Cottage in Morrow

Rossburg Tavern (1800’s)

This house was built in the early 1800's as part of a small town "Rossburg" that no longer exists and is reported to have been a Tavern. This is one of the last remaining structures for this town along with the barn and house across the street. The house sits on one acre of land surrounded by farmland, so you'll have opportunity to relax by a campfire, enjoy the unique architecture of the house, or explore the wide variety of entertainment options all within 20 minutes of the house.

4.98 out of 5 average rating, 142 reviews

A dining area features a wooden table set for four, complete with plates and glassware. Soft lighting is provided by a chandelier above. Dark leather chairs surround the table, and a sign with the word 'blessed' is mounted on the wall, complementing the modern kitchen visible in the background.

Flat in Monroe

Newly Remodeled Two Bedroom rental unit

Newly Remodeled, Pet Friendly, King & Queen Beds, Washer&Dryer in unit, Smart TV's in every room, Alexa, Keyless Entry. For children: high chairs, Pack and Play's with thick mattresses, Air Mattress. 2 miles from I-75, Close to Kings Island, Miami Valley Gaming Casino, Flea Markets, Premium Outlet Mall, Centrally located between Dayton and Cincinnati, 30 minutes to Cincinnati Reds, Bengals, Dayton Dragons. Close to Lebanon Sports Complex & Warren County Sports Park

4.97 out of 5 average rating, 101 reviews

The entrance to the home is shown, featuring a welcoming porch with two rocking chairs and a decorative entry sign. A clean concrete path leads to the front door, and the surroundings include a landscaped area with gravel and a green lawn, alongside a white fence.

Home in Lebanon

Bungalow in Downtown Lebanon

Welcome to your newly renovated one-bedroom home! This chic retreat features a spacious king bed and a comfy pull-out couch with a mattress topper for extra coziness. The gleaming kitchen boasts brand-new appliances, perfect for culinary adventures. Step outside to your private back patio, complete with a Solo Stove for warm, relaxed evenings. Plus, enjoy the convenience of being within walking distance to the vibrant downtown scene. Your ideal home away from home awaits!

4.89 out of 5 average rating, 197 reviews

A single-story house is depicted, featuring light-colored siding and a sloped roof. A two-car garage is present, with a neatly paved driveway leading to the entrance. Lush green grass surrounds the home, complemented by a leafless tree in the front yard.

Home in Middletown

New home & huge yard! 3-bd, 2 baths with game room

Enjoy our spacious master bedroom, brand new furniture, peaceful backyard with a 2 person hot tub, BBQ grill, fully equipped kitchen, game room, convenient parking, and 3 spacious bedrooms. We have everything you need to stretch your legs and relax. Ideal for visiting sights in Cincinnati (25 min) or Dayton (15 min) as well as King's Island (15 min). Close to shops, restaurants, and entertainment. Kids and families are welcome!

4.92 out of 5 average rating, 179 reviews

A modern two-story building is framed by lush greenery and mature trees, featuring a mix of dark wood and stone accents. Large windows provide natural light, while a curved pathway leads to the entrance, enhancing the inviting exterior.

Flat in Tipp City

Heartland - 2nd Floor Upper Level

Kick back and relax in this calm, stylish space. We invite you to exlore this hidden gem just outside of Tipp City, OH. Guests will enjoy a private bedroom, bathroom, kitchen, living area, and designated patio space all to themselves. Guests will enjoy the tranquil atmosphere and beautiful natural landscape with nearby biking or hiking trails. Grill out, make a fire, enjoy peaceful walk on the labyrinth and so much more.

4.98 out of 5 average rating, 162 reviews

The living room showcases a cozy seating arrangement with a patterned couch and armchair. A wooden coffee table is placed on a textured rug, and a wall-mounted television is visible. Natural light enters through a large window, framed by orange curtains.

Cottage in Hamilton

Four Mile Creek Cottage - Countryside Getaway

Relax and unwind with the whole family at this peaceful countryside getaway. Situated on 4 acres of woodlands greenery, directly overlooking Four Mile Creek, the cottage is tucked away from city noise yet super accessible: 5-minute drive to Spooky Nook Champion Mill and Downtown Hamilton, 15-minute drive to Miami University and Uptown Oxford, 50-minute drive to Cincinnati, 1-hour drive to Dayton, Ohio.

A dining area features a rustic wooden table set with a woven runner and a decorative vase containing fresh flowers. Surrounding it are four white, cushioned chairs. The space is brightened by natural light coming through large windows, with a cozy living area visible in the background.

4.93 out of 5 average rating, 207 reviews

Updated home in Dayton with low fees!

This unique home in Dayton is loaded with charm. It has been updated in all of the right places to maintain its original character while providing all of the amenities you desire. You'll get quartz countertops, new appliances, high-end mattresses, brand new wood bedframes, and a sit-in front porch. Whether you are here for work or play, this home will be a great "home away from home".

A well-appointed kitchen and living area is showcased, featuring a black sectional sofa with a soft throw. Light wood flooring complements the white cabinetry and modern appliances, including a microwave and a stove. A stylish wall featuring intricate tile patterns adds character.

4.91 out of 5 average rating, 139 reviews

Petite Paradise: Charming Tiny Home!

Tiny Home! Enjoy 420 sq home, a private fenced-in yard for your furry friends! Relax on the spacious sun deck or take advantage of the large side yard—ideal for running and playing with your dog. Plus, unwind by the cozy fire pit with provided wood and a swing for ultimate relaxation. Perfect for pet owners and nature lovers alike!

4.95 out of 5 average rating, 226 reviews

An A-frame structure with a distinctive red roof is positioned near the Stillwater River, surrounded by bare trees and lush green grass. A wooden deck extends towards the water, while a firepit with seating is visible in the foreground, enhancing the outdoor setting.

Tiny home in Dayton

Sleep Riverside Surrounded by Fall Foliage

🏡Welcome to La Casita Cardinal, a cozy 320 sq ft A-frame nestled along the serene Stillwater River, offering over 450 ft of scenic riverfront. Tucked behind main homes on a tranquil lane near the historic Buckhorn Tavern, this peaceful hideaway is ideal for couples, solo travelers, and nature enthusiasts.

Popular amenities for Middletown pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.98 out of 5 average rating, 135 reviews

A spacious living area is adorned with a light-colored seating arrangement that includes sofas and chairs. A wooden coffee table sits centrally, while large windows allow natural light to illuminate the room. The kitchen area is visible in the background, featuring modern appliances and a cozy dining space.

Home in Kettering

GORILLA HOUSE DAYTON

4.95 out of 5 average rating, 37 reviews

The exterior of a modern two-story home is presented, featuring a combination of white and dark blue siding. A prominent gabled roof and wooden accents frame the front door. A driveway leads to a two-car garage, and landscaping includes low bushes and a lawn.

Home in Middletown

NEWLY built sanctuary. Come make yourself at home!

A brick house with a well-maintained lawn is shown, featuring a single-car garage and a paved driveway. Neatly trimmed shrubs and flowering plants are positioned around the front entrance. A clear sky with scattered clouds is visible in the background.

4.91 out of 5 average rating, 103 reviews

Mama Mia’s Chic house!

4.92 out of 5 average rating, 346 reviews

The front porch of a charming home features white columns and a welcoming entrance. Lush green grass and colorful flowerbeds with blooming roses frame the walkway. Potted plants accentuate the adjacent properties, contributing to the neighborhood's inviting atmosphere.

Home in Ludlow

♥Historic Home on KY Bourbon Trail!♥Mins 2 Cincy!♥

4.91 out of 5 average rating, 223 reviews

A spacious living area is furnished with a dark sectional sofa and accented by decorative pillows. Light hardwood flooring complements the light gray walls. A large TV is positioned on a modern white cabinet, while natural light streams through white curtains, enhancing the room's openness.

Home in Cincinnati

Serene Stay in Central Cincinnati

5 out of 5 average rating, 77 reviews

A bright living room features two comfortable armchairs and a stylish sofa, arranged around a central coffee table. Decorative wall art frames are displayed above the sofa. A light fixture hangs from the ceiling, while a front door invites natural light and views of the outside.

Home in Lebanon

Walkable on E. Warren St.

4.69 out of 5 average rating, 32 reviews

The living area features a light-colored dresser topped with a television, displaying a serene fireplace scene. Decorative wall art is seen alongside a stylish mannequin. A green plant adds a touch of nature, while the wooden floor contrasts with the gray walls.

Home in Middletown

Cozy cottage in North Middletown

4.99 out of 5 average rating, 201 reviews

The living area features exposed brick walls and wooden beams, creating a blend of rustic and modern design. Comfortable seating is arranged around a central coffee table, with a large rug underfoot. A flat-screen TV is mounted on the wall, and natural light filters through large windows.

Home in Cincinnati

Charming Carriage House

Pet-friendly home rentals with a pool

5 out of 5 average rating, 4 reviews

The Paper Plane: Pool|Sauna|Poker Room|Sleeps 8

4.9 out of 5 average rating, 78 reviews

Home in Mason

Private Pool, Firepit, BBQ - A FUN place to RELAX.

4.94 out of 5 average rating, 94 reviews

A spacious home is set on a lush green lawn, surrounded by trees. A large circular driveway leads to the entrance, which features a welcoming porch. A separate garage structure is visible in the background, emphasizing accessibility within the tranquil landscape.

Home in Aurora

Unique Luxury Family Retreat

Apartment in Over-The Rhine

A well-maintained outdoor pool is surrounded by spacious patios and modern lounge chairs. The pool area is framed by an array of large windows from the surrounding building, allowing for natural light to flood the space. Green plants are positioned throughout for added ambiance.

4.95 out of 5 average rating, 57 reviews

Apartment w/Pool+Gym+ Free Onsite Parking

5 out of 5 average rating, 24 reviews

A single-story red brick house is displayed with a neatly manicured lawn. The front porch is adorned with white railings and supported by two columns. An American flag is mounted on the porch. Large windows and decorative shutters enhance the façade.

Home in Hamilton

Kingston Cottage Retreat

4.95 out of 5 average rating, 22 reviews

Family or Work Guest Cottage Next to Amazing Deli

4.89 out of 5 average rating, 46 reviews

A modern kitchen area features wooden cabinetry in contrasting tones and stainless steel appliances, including a microwave and stove. A small workspace with a chair sits adjacent to a decorative green wall. Natural light fills the space through glass doors leading to an outdoor area.

Flat in Over-The Rhine

OTR | King Bed l Free Parking | Gym | Top Floor

4.84 out of 5 average rating, 473 reviews

An inviting living space features a small dining table with two high chairs and a cozy seating area, including a light-colored armchair and a textured rug. The kitchen showcases modern cabinets and a subtle backsplash, while natural light streams through the nearby windows.

Flat in Pendleton

Stylish Flat w/ Parking Walkable

Private, pet-friendly home rentals

5 out of 5 average rating, 41 reviews

A cozy living area features a brown leather sofa and armchairs, paired with a decorative pouf. Natural light is provided by the adjacent windows, while a small table holds a potted plant. A television is positioned nearby, complementing the warm, inviting space.

Flat in Lebanon

Main Street Cottage No. 2

4.96 out of 5 average rating, 78 reviews

The exterior of a renovated home is showcased, surrounded by lush green grass and wooded areas in the background. Multiple windows reflect the natural light, and a covered entrance with a central door is visible. The building features a mix of stone and siding.

Flat in Loveland

Spacious Studio cottage near downtown Loveland

4.91 out of 5 average rating, 93 reviews

A well-lit bedroom features a spacious bed covered with a light blanket, positioned on a large area rug with floral patterns. Two windows allow natural light to enter, while a desk with a chair and a fan are situated against one wall. Decorative plants add a touch of greenery.

Home in Kettering

Lively 2 BR by The Greene/Hospitals/Fraze Pavilion

4.83 out of 5 average rating, 12 reviews

A spacious living area features a gray sofa, a coffee table, and two black chairs. A television is positioned on a low console, and the kitchen area is visible with white cabinetry and appliances. Natural light enters through a window, illuminating the open layout.

Flat in Franklin

Cozy Retreat Washer/Dryer Inside

A well-lit bedroom features a spacious bed with a cozy gray throw blanket. Dark curtains frame the windows, allowing natural light to filter in. A round mirror hangs above a modern dresser, complemented by a decorative plant and a bedside lamp.

4.96 out of 5 average rating, 26 reviews

Charming 2 Bed w/ King Near UD/WSU/DT/ Hospitals

5 out of 5 average rating, 19 reviews

Flat in Hyde Park

Basic Bryn (7) - Purple Pillows/Mattress/Sheets

A charming cottage exterior features a yellow façade complemented by green shutters. A metal roof adds character to the structure, surrounded by manicured bushes and a grassy yard. A stone walkway leads to the welcoming front porch, framed by trees in a serene woodland setting.

4.95 out of 5 average rating, 86 reviews

Shakertown Cottage-Your Home Away From Home!