Family-friendly vacation 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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Top guest favorite
Guest suite in Yellow Springs
4.99 out of 5 average rating, 496 reviews

Family- and Eco-Friendly Studio Close to Downtown

* Great play spaces for kids of all ages * 7-minute walk to downtown Yellow Springs * Large table for working, crafting, eating * Free parking for up to four vehicles * Great amenities * 4 Comfy beds (king bed, full bed, full sofa bed and queen air mattress) * Super clean Close to: - Parks & playgrounds - Dave Chappelle shows - Shopping - Restaurants - Glen Helen Nature Preserve - Scenic bike path - and more. It is not suitable for those with difficulty climbing stairs.

Top guest favorite
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.
Guesthouse in Maineville
4.95 out of 5 average rating, 275 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

Guest favorite
A cozy living area features a spacious sofa and a wooden chair positioned beside a wood-burning stove. Natural light fills the room through two windows adorned with sheer purple curtains. A decorative area rug lies on the wooden floor, with a mirror reflecting the serene outdoor view.
Cottage in Somerville
4.88 out of 5 average rating, 103 reviews

Quaint Stream Side Cottage 15m Oxford&Hamilton Oh

Charming and quaint 800sqft cottage on a beautiful farm in the hills! Come relax in a corner of nature just 15min East of Oxford, Ohio. Wake up to a small stream, and the distant gentle sound of nature and farm animals awakening. Plus amazing views on the horizon. Soak up the enjoyment of natures small little expressions. This cottage accommodates 1-5 guests with one queen bed, a full size sleeper sofa and a very comfy twin mattress. Comes with an equipped kitchen and high speed internet.

Top guest favorite
Guesthouse in Waynesville
5 out of 5 average rating, 167 reviews

Greystone Cottage in Historic Waynesville

Peaceful cottage on Main Street, just outside the business area. Walk to the shops and restaurants or bike .6 miles to the Ohio to Erie Trail. Equipped kitchenette sufficient to prepare light meals, outdoor grill, patio and lawn for outdoor games. Queen bed and Queen sleeper sofa. There is room for inside bike storage. Greystone Cottage is located close to the Little Miami Bike Trail, canoeing, King’s Island, the Ren Fest, Caesar's Creek, walking distance to restaurants and unique shops.

Top guest favorite
Guesthouse in Lebanon
4.95 out of 5 average rating, 502 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 favorite
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.
Guesthouse in Hamilton
4.98 out of 5 average rating, 254 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 favorite
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.
Apartment in Monroe
4.97 out of 5 average rating, 158 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 favorite
An elegant bungalow is showcased, featuring a light blue exterior with black shutters. The porch, supported by white columns, creates a welcoming entrance. Surrounding greenery and a large tree provide shade, complemented by a fenced yard. The inviting structure reflects its historic charm.
Bungalow in Springboro
4.96 out of 5 average rating, 122 reviews

Best Location in Springboro Ohio!

Welcome to Stayin on Main, our charming bungalow located in historic downtown Springboro. We are located Two miles off of 1-75., between Dayton and Cincinnati. The unit was completely renovated in 2019. Everything is new, plumbing, cabinets, electricity, furniture, and appliances. Shopping, restaurants, and major attractions, for example, WPAFB, National Air Force Museum, Wright State, Kings Island, UD, Lacomedia Dinner Theater Waynesville, and Lebanon. And much more...

Guest favorite
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, 214 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.

Guest favorite
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, 232 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 favorite
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.
Apartment in Oregonia
4.99 out of 5 average rating, 145 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.

Top guest favorite
The exterior of a single-story brick home is shown, featuring a double garage, manicured lawn, and flower beds with yellow blooming flowers. A driveway leads up to the home, surrounded by peaceful greenery and trees in the background.
Apartment in Middletown
5 out of 5 average rating, 163 reviews

SouthView Acres (No Hidden Fees!)

We are ready to welcome you to SouthView Acres! Enjoy a comfortable stay in our mother-in-law suite with its own private entrance. Private parking, quiet location and minutes away from I75 access. Enjoy cable TV and wifi. Our home is on 10 acres where you are welcome to walk the trails or warm yourself by the fire pit at night. A convenient location for business or pleasure travelers. No hidden fees.

Popular amenities for Middletown family-friendly rentals

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

  • Total vacation rentals

    Explore 30 vacation rentals in Middletown

  • Nightly prices starting at

    Middletown vacation rentals start at G$10,464 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,110 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 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!