Family-friendly vacation rentals in Middletown

Retreat to a Boho Chic Guesthouse in a Leafy Family Suburb

Get comfy swaying in the macrame hammock in a living room with a Moroccan vibe. Make breakfast in the bright kitchen and snuggle up on a cozy banquette. This guest house shares a driveway with our home, but it is completely detached and private. The bedroom sleeps two on a queen mattress, and we provide a queen sized inflatable mattress that fits easily in the living room. The property has a stocked kitchen, a washer and dryer, a lovely new bathroom, a two-car garage, and loads of aesthetic.

Tranquil Nest - Family Home with Spa Tub

Nestled in a wooded neighborhood, our home, ideal for family or friends, is just minutes away from I-75, local dining, entertainment, downtown Dayton, and Dayton International Airport. Enjoy a spacious backyard, a fully-equipped eat-in kitchen, a dedicated workspace, and an attached two-car garage. Unwind in one of the three plush bedrooms, one boasting an en-suite with a jacuzzi tub and seated shower. Experience comfort and convenience at our charming retreat. We look forward to hosting you!

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.

Comfortable Studio In Springboro

Welcome to a quiet, upscale golf course community within walking distance to Old Towne Springboro. Private 438 square foot studio apartment with a king bed, full bath, large kitchen and in unit washer and dryer. This guest suite has its own entrance that is accessed with a keypad. Location: Nestled in the Heatherwoode Golf Course community within walking distance to Old Towne Springboro and 10 min from Austin Landing. 15 minutes from Kings Island and Cincinnati Premium Outlets.

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...

4-Beds: Firepit / Game Consoles / Workstation

Please see other notes for rules / disclaimers. Half a mile from Spooky Nook & blocks away from the new Agav & Rye. At 'The Sunset Nook', we have taken every effort to add every amenity possible to make a perfect experience. One block away from Sutherland family Park (See Pics). Our home is surrounded by landscape lighting to create a relaxing/secure environment. Our guest comfort and security is a top priority; spotlight/security cameras monitor the property for guests.

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.

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.

The Cottage Retreat

Whether you are looking for a place to spend some time or just passing through we think you’ll find it quite lovely here. We are just 5 mile off of I70 and centrally located among many places of interest. Go out or stay in. The outdoor living space is pretty spectacular! Private, with a hot tub, fire pit (wood provided), turf to play corn hole. Inside delivers all the comforts of home with full kitchen, laundry, workspace and cozy fireplace.

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!