Family-friendly holiday rentals in Montgomery County

South Park Guest House

Historic South Park guesthouse. Built as the center of 3 sisters, this 1920 shotgun cottage and its neighbor to the right were bought by me, a neighborhood activist, who stripped them both down to the studs. What you'll find is a mix of historic, modern, and mid-century modern, with vaulted ceilings with skylights in both the bedroom and the spacious bathroom, and safe, snug, and quiet thanks to the insulation, new windows, new doors, and Berber carpet. Owned by a Certified Service Disabled Vet.

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!

* Cozy 2 bedroom home with 2 TV’s *

Relax & unwind alone, or with your family in our cozy home! Fast WiFi Fully stocked coffee bar. Conveniently located 10 minutes from the Dayton Airport, and 14 minutes to downtown Dayton. 11 minutes to Rose Music Center. Restaurants and shopping within walking distance, and Metroparks bike trail at the end of our street. Dogs are welcomed for an additional fee. No cats. Unique quirks about our little home: the ceiling coming down the steps is lower, and the bathroom is a jack-and-jill.

Vagabond’s Tiny Art Gallery BnB

Vagabond offers a cozy stay and light breakfast in an INCLUSIVE and WELCOMING mellow, private Tiny Art Gallery BnB. Located on a tree lined street in a 1940’s neighborhood, walking distance to Trader Joes, restaurants, boutiques, Fraze Pavillion and Lincoln Park. 10 minute commute downtown to sites like; UD, Dayton Art Institute, Carillon Historic Park, Levitt Pavilion, Oregon District, Front Street, Schuster, Riverscape, etc. Don’t miss Dayton’s stellar local arts and music scene!

Luxury & Wellness

Discover a sanctuary of wellness and luxury in the heart of Dayton, Ohio. Our exclusive three-bedroom, two-bath home is not just a place to stay, it's an immersive bio-hacking experience designed to rejuvenate your mind, body, and soul. Here, health technology isn't just an amenity, it's a way of life offered to our guests at no extra cost. You have seen celebrities like Joe Rogan embrace these technologies on social media, and now it's your turn to experience their transformative power.

Home w/King Suite 4 Mins to DAY Airport

Open Floor Plan. King Suite with Work Station. Private Garage. Fenced in Backyard. Hard Top Canopy on Deck. Spacious 2nd Floor Bedroom. Pet Friendly. Coffee / Tea Bar. Wifi Door Locks. Wifi Available NO PARTIES ALLOWED Pets allowed with $50/pet fee charge

Luxury Oregon District Home - Heated Pool

This HUGE luxury 5,000+ sq ft home is perfect for big groups, such as wedding party getting ready and event use to stay for the entire weekend. Close to all downtown wedding venues (The Steam Plant, Brightside, The Lift, Dayton Arcade, etc.) Comes with a huge backyard space with an in-ground heated pool, fire pit, outdoor dining, and attached gravel parking lot. This home is adorned in Gucci wallpaper and the finest finishes around; not one detail was spared. Perfect for photo ops!

Sweet & Cozy Cranberry Cottage in a vintage barn!

Welcome to the Cranberry Cottage! Enjoy the rustic barn experience while enjoying modern conveniences of this sweet romantic cottage. You'll feel like you're a million miles away from the hustle and bustle while you enjoy coffee on your own private deck. Walk up the path and cross the road and you can enjoy 150 acres with walking trails at Mount Saint John. This cottage in conveniently located close to major highways, shopping, dining and nature. Come enjoy this unique experience.

Huber Heights Hot Tub Bungalo

Forget your worries in this spacious and serene space only 2 miles away from the Rose Amphitheater, new Bucee's and 10 minutes from downtown Dayton. Spacious backyard equipped with 113 jet hotub and a firepit. The sunroom is a great spot to start the day with complementary coffee/creamer. Complete with 4 Tvs and a computer. The living room has a Nintendo Switch for family fun. Have both a charcoal and gas grills. Please take note. The pool is taken down in September.

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.

Carillon Cottage - Modern Comfort & Vintage Design

Carillon Cottage is a historic home featuring modern comfort with vintage design. This family-friendly and spacious house, which was originally built in 1905 and fully renovated in 2023, is filled with details highlighting the rich history of Dayton, Ohio. Enjoy the curated display of local photos and elegant furnishings with classical touches. We look forward to hosting you!