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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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Apartment in Fairborn

4.9 out of 5 average rating, 480 reviews

World Traveler! WPAFB,Coffee,W/D,Business,Ext-Stay

Experience this executive style studio apartment, enjoy your stay in style! 10 minutes to Air Force Museum, Wright State University, Nutter Center, Fairborn Library, YMCA, Central Park w/ play area/free Splash Pad! 15 -20 minutes to Dayton, University of Dayton(22min), I-75, I-70, Yellow Springs, Young's Jersey Dairy Farm, John Bryan State Park, Rose Music Note: Strict cleaning and sanitizing measure are in place to ensure the health and safety of our guests. Thank you for your understanding.

May 7 – 14

R1,510 ZAR per night

Guest suite in Yellow Springs

4.98 out of 5 average rating, 383 reviews

Hoot 'n' Haller Studio

My studio is close to parks, art and culture, shopping, restaurants and dining, great views, hiking at Glen Helen Nature Preserve, and the bike path. You’ll love this new space with modern styling, fun furniture, and lots of space. It's perfect for couples, solo adventurers, business travelers, and families with kids. It was built as a maker's studio, so it's great for small retreats for sewers, knitters, and scrapbookers, as well. It is not suitable for those with difficulty climbing stairs.

Nov 20 – 27

R2,771 ZAR per night

Cottage in Dayton

4.98 out of 5 average rating, 258 reviews

The Blue Heron Guest House

Whether you are traveling solo for work, or for recreation with your family, our lovely two bedroom, 1200 square foot guest house is ideal. One of two houses on the property (we live in the other) designed and built in 1920 as a summer residence for a local family. These 5.5 acres of park-like setting are situated on the serene Stillwater River. Tucked away, in the midst of the suburbs, surrounded by trees, gardens and the sound of birds, this gem of a place is a perfect home away from home.

Feb 13 – 20

R2,286 ZAR per night

Apartment in Hamilton

4.97 out of 5 average rating, 191 reviews

Apt B at The Benninghofen House

Welcome to The Benninghofen House, a boutique hotel and venue in the heart of Hamilton, Ohio. A Queen Anne Victorian in the historic Dayton Lane neighborhood, we are near Spooky Nook Sports Champion Mill, Miami University, Pyramid Hill Sculpture Park, The Donut Trail, Lake Lyndsay, The Benison, Jungle Jim's, Kings Island, disc golf, and more! We offer 4 rental apartments. Guests can enjoy our lush backyard and grand front porch. Schedule yoga and massage or a private event during your stay.

Aug 14 – 21

R3,492 ZAR per night

Home in Dayton

4.95 out of 5 average rating, 273 reviews

“Helen’s House” Granny Chic 2 Baths 2 Beds

Helen's House is ideally located in Southeast Dayton near the I-75 interchange. Just 1.5 miles from the city center. Close to the University of Dayton Campus, Wright Patterson Air Force Base, the historic Woodland Cemetery. Grocery stores and restaurants are 2-10 minutes from the home. Built in 1900 with original woodwork and wallpaper, we offer the ultimate Granny Chic experience and a step back in time. Helen's House is perfect for couples, adventurers, business travelers, and families.

Feb 19 – 26

R1,927 ZAR per night

Loft in Lebanon

4.9 out of 5 average rating, 164 reviews

Wonderful spacious loft in downtown Lebanon Ohio

Simplify Guest Homes are located inside a beautiful historic building located on Mulberry Street and Mechanic, right in the heart of downtown Lebanon. Available is Simplify 1 located on the top floor along with Simplify 2 below. Both offer a cozy and clean environment. Whether you want to hang out with friends and family or explore the town, this is the perfect space for that. Almost everything is walking distance from Simplify with many cafes, eateries and stores in the surrounding area.

Dec 18 – 25

R3,225 ZAR per night

Home in Dayton

4.89 out of 5 average rating, 407 reviews

Air Force Museum Getaway! WPAFB & Downtown too...

The best place to stay when visiting the National Air Force Museum. It's open year round, entrance is free, and you even can walk there if you want :) You will also be very close to all the Wright Patterson AFB entrances and only 5 minutes to Wright State University, only 10 minutes to the Nutter Center (for watching various shows) and Downtown Dayton - including the Oregon District, University of Dayton, Schuster Center, Miami Valley Hospital, and others. Perfect for vacation or work!

Jul 4 – 11

R1,979 ZAR per night

Tiny home in Yellow Springs

4.98 out of 5 average rating, 486 reviews

Yellow Springs Tiny House

The Yellow Springs Tiny House is a super insulated 400 square foot energy efficient home, partially powered by solar panels. You have all the amenities of a home including laundry, fully equipped kitchen, private bathroom, loft area, cathedral ceilings, high speed internet with smart TV (Netflix, Prime, Hulu, YoutubeTV, Disney+). It is all new, opened in June 2018. Just a few blocks from downtown, bikeway, Yellow Springs Brewery, Mills Park Hotel, Little Art Theater, and more.

Jan 4 – 11

R2,109 ZAR per night

Guest suite in Yellow Springs

4.89 out of 5 average rating, 405 reviews

Spring Lea Loft Apt - for Nature Lovers - GoSOLAR!

Private large Studio Apartment, upper story of building, private entry & parking, kitchenette, washer/dryer, Mini-split AC/Heat. Solar powered w/grid 1.5miles from YS. Glen Helen hiking nearby, J. Bryan State Park up the road/trail. Bike roads & bike trail. Basic kitchen needs provided - HotPlate, microwave, Kuerig, fridge/freezer, table & 2 chairs, Queen Bed & New fullsize futon couch No Pets due to allergies. We'd love to host your stay in Y.S.! Great place for outdoor lovers!

Jul 15 – 22

R1,755 ZAR per night

Farm stay in Xenia

4.91 out of 5 average rating, 524 reviews

Chicken Coop Extraordinaire

Come roost in our chicken coop! DIRECT ACCESS TO OUR NATION'S LARGEST NETWORK OF PAVED TRAILS! Bike available to borrow. Boat available for a moonlit cruise. Our 1800's homestead was a stop on the Underground Railroad & a land grant to a Revolutionary War Veteran. Modern amenities with 1 bedroom & roll away bed for an additional guest. Complete kitchen with milk, juice, oatmeal & farm fresh eggs! Campfire & gas grill available. Trailer parking. Shuttle to nearby restaurants.

Apr 9 – 16

R2,105 ZAR per night

Home in Hamilton

4.94 out of 5 average rating, 142 reviews

Country Estate Home

When you pull in you will first notice the big green space of 3+ acres to enjoy with your family. Once inside this classic brick estate home you will find 5 bedrooms, eat in kitchen, family room and formal dining room. All the comforts of your own home while you are away, including grill/outdoor area, laundry, fully furnished kitchen with cooking/dishware/vitamix. Great for parents visiting college students, an escape with friends, & families traveling with loved ones.

Oct 27 – Nov 3

R8,045 ZAR per night

Guest suite in Park Hills

4.98 out of 5 average rating, 292 reviews

A Place For Everyone/ NO STEPS/ No Cleaning

This is my personal home and I welcome you to be my guest, relax, make yourself at home and leave the cleaning to me. My favorite things are the accessibility features, the privacy, and no steps. There is 1 Bedroom with Queen bed, a Queen size bed Murphy Hutch, 2 couches and a twin air mattress. Private suite on ground level of house (private entrance) in beautiful Park Hills. You have your own parking right next to your entrance and close to everything.

Dec 6 – 13

R1,685 ZAR per night

Vacation rentals for every style

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Popular amenities for Middletown family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Cabin in Richmond

4.89 out of 5 average rating, 242 reviews

Cozy cabin w/ pool, hot tub, gazebo & gardens

Sep 9 – 16

R3,547 ZAR per night

Cabin in Loveland

4.93 out of 5 average rating, 76 reviews

Log Cabin w/ Hot Tub on Ranch w/ Lake!

May 12 – 17

R15,263 ZAR per night

Home in Covington

4.92 out of 5 average rating, 289 reviews

3 BR House 3.5 miles from Downtown Cincinnati

Aug 3 – 10

R5,504 ZAR per night

Home in US

4.82 out of 5 average rating, 110 reviews

1905 Queen Ann Historic Mansion

Jul 17 – 24

R18,586 ZAR per night

Family- and pet-friendly home rentals

Home in Loveland

4.77 out of 5 average rating, 286 reviews

Harper, Two Bedroom House in Historic Loveland

Mar 23 – 30

R1,759 ZAR per night

Home in Dayton

4.88 out of 5 average rating, 209 reviews

Dayton Dreamcatcher House

Jun 25 – Jul 2

R2,099 ZAR per night

Home in Cincinnati

4.9 out of 5 average rating, 183 reviews

Serene Stay in Central Cincinnati

Oct 13 – 20

R3,771 ZAR per night

Cabin in Burlington

4.84 out of 5 average rating, 122 reviews

Rabbit Hash Apartment, Creation Museum, Ark,Casino

Dec 30 – Jan 6

R2,650 ZAR per night

Home in Cincinnati

4.94 out of 5 average rating, 365 reviews

Private 1br apt near OTR/downtown Cincinnati

Sep 29 – Oct 6

R1,392 ZAR per night

Apartment in Yellow Springs

4.96 out of 5 average rating, 472 reviews

The Downtown Den at the 1866 House

Sep 8 – 15

R3,470 ZAR per night

Home in Dayton

4.93 out of 5 average rating, 186 reviews

Entire house- Dayton/U D /KETTERING/OAKWOOD /WPAFB

Jul 3 – 10

R3,612 ZAR per night

Apartment in Covington

4.97 out of 5 average rating, 518 reviews

The Slanted House - “marvelous gem of a home”

Dec 20 – 27

R2,669 ZAR per night

Family-friendly home rentals with a pool

Home in Highland Heights

4.81 out of 5 average rating, 139 reviews

☆Riverview ☆Close to Downtown ☆Lrg Modern Home

Nov 10 – 17

R6,862 ZAR per night

Apartment in Cincinnati

4.88 out of 5 average rating, 702 reviews

Hip Eclectic 1 bedroom in OTR w/free parking

Apr 20 – 27

R1,930 ZAR per night

Home in Lawrenceburg

4.8 out of 5 average rating, 167 reviews

Downtown Lawrenceburg

Sep 5 – 12

R2,635 ZAR per night

Condo in Cincinnati

4.84 out of 5 average rating, 106 reviews

Come for a Romantic Stay & enjoy this bliss

Apr 7 – 14

R2,782 ZAR per night

Home in Cincinnati

4.91 out of 5 average rating, 264 reviews

Luxury OTR Townhome w/ Large Private Rooftop Patio

Aug 15 – 22

R4,264 ZAR per night

Apartment in Cincinnati

4.83 out of 5 average rating, 456 reviews

Spacious Home: Walk to Everything & FREE Parking

Nov 22 – 29

R5,359 ZAR per night

Home in Lebanon

4.92 out of 5 average rating, 79 reviews

Big Families Welcome

Apr 16 – 23

R19,607 ZAR per night

Home in Loveland

4.73 out of 5 average rating, 139 reviews

4BR Retreat w/ Pool backing up to Farm

Nov 7 – 14

R15,040 ZAR per night

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

Total rentals
50 properties
Wifi availability
50 properties include access to wifi
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Total number of reviews
590 reviews
Nightly prices starting at
R371 ZAR before taxes and fees

Destinations to explore