
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.

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.

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

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.

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.

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

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.

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

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...

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.

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!

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.

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
Family-friendly home rentals with a hot tub

Modern Remodel Steps to Downtown, Glen, & Antioch

Nature Spa House | •Pool •Hot Tub •Sauna •Pvt Lake

The Cottage Retreat

Boutique Stay - Hot Tub, Home Office & Fenced Yard

The Homespun Landing

Spacious 4BR Ranch w Hot Tub in Quiet Neighborhood

Arcade + Hot Tub Retreat | Sleeps 8 | Near WPAFB

Stargazers' Retreat: A Tiny Home on the Riverside
Family- and pet-friendly home rentals

Loveland Farm 26 Beautiful Acres 3 ponds

Home in Xenia

Entire Home close to uptown Oxford and Miami U

Jesse Brooke Farm

Cozy Country Studio Suite

Heartland - 2nd Floor Upper Level

Walk to Trails! 5mi to Day Airport

StayStonybrook - Fairfield Township
Family-friendly home rentals with a pool

Peaceful Paradise LOWER Fam 2BR Hot Tub/Pool/SAUNA

2A2J Barn Getaway/ beautiful Pool and Sauna

Downtown Lux Stay with Pool

Lake Front w/ Pool! Between Ark & Creation Museum.

Mod Lodge Close to Cincinnati Big Pool EV Charger

Downtown Loft with Pool & Rooftop

Huber Heights Hot Tub Bungalo

Art Studio at Turtle Hill, 5-Acre Oasis Near City
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!
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- Kings Island
- Great American Ball Park
- Creation Museum
- Cincinnati Zoo & Botanical Garden
- Perfect North Slopes
- Cincinnati Music Hall
- Newport Aquarium
- Paycor Stadium
- University of Cincinnati
- John Bryan State Park
- Duke Energy Convention Center
- University of Dayton
- Cincinnati Art Museum
- Xavier University
- Heritage Bank Center
- Smale Riverfront Park
- Hard Rock Casino Cincinnati
- Big Bone Lick State Historic Site
- Jungle Jim's International Market
- TQL Stadium
- National Underground Railroad Freedom Center
- Eden Park
- Contemporary Arts Center
- Krohn Conservatory





