Family-friendly holiday rentals in Middletown

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Middletown

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite
A vibrant kids' playroom features a colorful climbing wall with various holds, a play kitchen, and a spacious area covered with a large, patterned rug. Light enters through a window, and playful animal illustrations adorn the walls, offering a cheerful environment for imaginative play.
Home in Liberty Township
4.9 out of 5 average rating, 105 reviews

KingsIsland~Sauna~Arcade~22miZoo~5Bd3ba~PlayArea

This property is your gateway to comfort and convenience. Unwind in the personal sauna room attached to the PrimarySuite, which offers a private retreat. The kids' playroom is a haven of joy, while the GameRoom promises endless entertainment. A fully equipped kitchen awaits your culinary adventures. This home ensures you're close to everything the city has to offer. Book now for a perfect blend of relaxation and exploration! 3mil LibertyCntr 3.9mil VOA 9mil KingsIsland/GreatWolfLodge 22mil Zoo

Guest favourite
A charming red barn-style guesthouse is shown among lush greenery, with wooden seating in the foreground. Seasonal decorations enhance the welcoming entrance, while a porch is visible, inviting relaxation. Tall grasses frame the scene, contributing to the peaceful atmosphere of the property.
Guest house in Maineville
4.95 out of 5 average rating, 259 reviews

The Barn at Serenity Acre

Take it easy at this unique and tranquil getaway, where relaxation abounds. We are located in Warren county, the playground of Ohio. - total and complete renovation in 2021 - fully equipped kitchen - cozy bedroom / living room - spacious bathroom with claw foot tub to soak or shower in, vanity, and robes - walking trails in woods behind our property, access to pool (seasonal), close to restaurants, stores, vineyard, historic towns, very close to Kings Island, bike trails, and so much more

Top guest favourite
Guest house in Lebanon
4.95 out of 5 average rating, 480 reviews

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

Guest favourite
The climbing gym features a wooden structure with high ceilings and sloped roofs. Colorful holds are mounted on the walls, complemented by various climbing accessories like mats and silks hanging from the beams. An inviting atmosphere promotes active engagement and community interaction.
Guest suite in Cincinnati
4.96 out of 5 average rating, 173 reviews

The CRUX Climbing Getaway

Welcome to The CRUX Sanctuary Community Climbing Gym! This retro inspired space is a perfect getaway for experienced climbers, small families, or anyone looking for a fun place to stay in Cincinnati. Conveniently located just 5 minutes from downtown Cincinnati, and a short drive from amazing views, diverse restaurants, and local attractions. This remodeled and 100% solar powered church is one of many unique spots in our Price Hill neighborhood. Find us by searching for thecruxsanctuary.

Top guest favourite
The historic home features a two-story façade with white siding and black shutters. A welcoming porch is highlighted by rocking chairs and potted plants. A well-maintained lawn adds to the inviting exterior, which showcases architectural details typical of early 19th-century design.
Home in Lebanon
4.99 out of 5 average rating, 163 reviews

General Mitchel Historic Home in Downtown Lebanon

Ormsby Mitchel was a Major General during the Civil War, and this was his home. This updated historic home was built in 1814 and is in the heart of downtown Lebanon. Local shops and restaurants are within walking distance. Easy access to local attractions like Kings Island and the Miami Valley Casino. We offer 3 bedrooms, 2 full baths, and plenty of space to spread out. A charming place to stay when traveling for work, a romantic weekend, a getaway with friends, or a family gathering.

Top guest favourite
The living area features wooden walls and a stone fireplace, complemented by soft-glow electronic candles. A cozy armchair is positioned near a window, while a round, textured coffee table sits at the center, adorned with a vase of dried flowers.
Guest house in Hamilton
4.98 out of 5 average rating, 248 reviews

Waterfront Cabin | Peaceful Pondside Escape

Seeking an escape for some peace and quiet? Welcome to The Little Cabin retreat, located on our 50-acre family farm in Ross, Ohio! Let us take you away from the distractions of life to a place where you can soak up nature in a cozy cabin, all within 30 minutes of downtown Cincinnati. You may fish in the lake if you'd like, or take a ride in the paddle boat, or simply enjoy sitting on the porch listening to the birds. Chances are, you may spot wild turkey or whitetail deer scampering by.

Top guest favourite
Tiny home in New Richmond
4.97 out of 5 average rating, 471 reviews

Stargazers' Retreat: A Tiny Home on the Riverside

Welcome to The Stargazers' Retreat at Visions on the River - A Tiny Home community on the Riverside. This newly built tiny home is #1 of 3 and set along the banks of the Ohio River, minutes away from the historic river town of New Richmond, OH and a 25-min drive to Downtown Cincy and Northern KY. This space is perfect for anyone looking to retreat and reconnect with nature. Take part in our adventure! With over 450 Five-Star happy guest reviews we are confident you will love it here!

Top guest favourite
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
4.97 out of 5 average rating, 153 reviews

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

Guest favourite
A cozy living area showcases two cream-colored couches positioned around a dark coffee table. Natural light enters through a large window, enhancing the space. A sleek ceiling fan is visible, and a small dining area is arranged with a table and two chairs against the wall.
Home in Miamisburg
4.94 out of 5 average rating, 204 reviews

The Linden Guesthouse - bike/hike/golf/shop/visit

This updated stylish 2 bed/1.5 bath single story guesthouse is perfect for work, group trips, fun, or family visits. The kitchen has dishes, cookware utensils, and pantry basics (oil, seasonings, sugar & flour). A Keurig single-serving and carafe coffee maker with k-cups and coffee filters is provided. The guesthouse has two living spaces, a dining room, a kitchen, a utility room with a washer and dryer, a private patio with outdoor seating, and a grill.

Top guest favourite
An inviting living area features a large brown leather sofa, a patterned area rug, and a decorative coffee table atop wide plank wood floors. A cozy corner chair and a lamp add warmth, while the back wall showcases a mural with 'Centerville Carriage.'
Guest house in Centerville
5 out of 5 average rating, 264 reviews

The Carriage House in the Heart of Uptown

The Carriage House in the Heart of Uptown Centerville!! Historic Charm with Modern Comfort. Built in 1897 and fully renovated in 2017, making it one of Centerville’s true hidden gems. Just steps from local restaurants, coffee shops and a scoop (or two) of Graeter’s Ice Cream. It’s perfectly located for your stay. Whether you’re planning a romantic weekend, visiting family, or simply looking to relax, this cozy retreat is the ideal place to unwind.

Guest favourite
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
4.9 out of 5 average rating, 218 reviews

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!

Top guest favourite
A spacious living room features warm hardwood flooring and ample recessed lighting. A large sectional sofa sits on a decorative rug, facing a flat-screen TV. Windows allow natural light to illuminate the space, with a bar area and a few stools in the background.
Flat in Oregonia
4.98 out of 5 average rating, 132 reviews

Green Acres Farm-Apartment

Reconnect with nature at this unforgettable escape on a farm in the heart of Warren County. Private 900 sq. ft. two bedroom, 1 bath, living room and kitchenette looking out over 18 acres of privacy. Minutes to Caesar’s Creek Lake and hiking trails, the Renaissance Festival, Little Miami River canoeing and bike trails, Kings Island and World Equestrian Center. Right in between Cincinnati and Columbus minutes off of I-71.

Popular amenities for Middletown family-friendly rentals

Quick stats about holiday rentals that are family-friendly in Middletown

  • Total holiday rentals

    Explore 30 holiday rentals in Middletown

  • Nightly prices starting at

    Middletown holiday rentals start at £37 per night before taxes and fees

  • Verified guest reviews

    Over 1,110 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 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!