
Vacation rentals in Oakwood
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Top-rated vacation rentals in Oakwood
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Private charming home w Fenced yard and fire pit
Chic Boutique is a lovely home in the heart of Dayton. Close to downtown, University of Dayton and both Miami Valley and Kettering hospitals. Our home is completely renovated and ready for your family to enjoy. We also have a fenced yard and parking in the driveway as well as on the street. You will love the private outdoor space for BBQ's or a cozy night lounging around the firepit. The kitchen is fully stocked for meal prep, and the kitchen table expands to seat 8 people. Relax and Enjoy!
4.94 out of 5 average rating, 212 reviews
Modern Historic House in the heart of South Park
Check out this stylish and modern home in the Historic South Park District centrally located in Dayton Ohio. Located on the best street in this trendy neighborhood where you can enjoy a view of the park from the porch. Built in 1880 this newly revamped home has an open concept full kitchen, 2 bedrooms and 2 full baths. Wood flooring and 12-foot ceilings throughout. Close to downtown, Miami Valley Hospital and the University of Dayton. Within walking distance to shopping, dining and much more.
5.0 out of 5 average rating, 185 reviews
In Kettering Near UD/Oakwood/Hospitals & Dayton
UD :University of Dayton,Kettering Oakwood. squeaky clean. 3 Smart TV's "High-Speed" Internet Minutes from Children's, Kettering & Miami Valley Hospitals .15 minutes: (DAY)Dayton Airport. :(CVG) Cincinnati Airport 55 min . Kitchen, Dining Rm, Living Rm, 2 bedrooms. work desk entire house! WPAFB museum,Grocery & shopping near. free parking.Screened porch. Quiet street.. Kurig coffee... located :Kettering. Near all major highways....bike paths, parks, hiking No parties Pets on approval.
4.93 out of 5 average rating, 225 reviews
Granny Chic Home. UD area. No cleaning fee. Unique
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.
4.94 out of 5 average rating, 385 reviews
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!
4.93 out of 5 average rating, 180 reviews
Bailey House
We love to maintain very high standards of cleanliness and have our guests feel at home. You will enjoy easy access to downtown Dayton, UD, the suburbs and all that Dayton has to offer. There is a lot of space for private parking, has a fenced backyard. This house is modern and has a spacious living room, dining area, fully equipped kitchen, four nice size bedrooms with closets, free private laundry, two full bathrooms, work space and play area with a nice aerial night view.
4.85 out of 5 average rating, 128 reviews
Peaceful 3BR House Minutes From Downtown Dayton!
Welcome and enjoy your trip in one of Dayton's best neighborhoods! Minutes from downtown Dayton as well as UD and Wright State. There is so much available at your fingertips. Wake up and grab a coffee at Epic Coffee. Stop by Trader Joes, Dorothy Lane, or Kroger to get your groceries. Take a walk through one of our spectacular parks nearby or catch a concert at Fraze Pavilion. This house is the perfect home away from home for you and your family to enjoy!
5.0 out of 5 average rating, 173 reviews
Dayton Retreat, UD, MVH, Oregon Dist, KHN, &WPAFB
Welcome to Polu, named after the Hawaiian word for “blue.” Located in Dayton’s historic South Park district, this beautifully restored 1800s home blends original architectural charm with modern luxury. Step inside to tall ceilings, preserved vintage details, and elegant, thoughtfully curated décor. Designed for comfort and relaxation, Polu offers a serene and stylish retreat whether you’re visiting for business, a weekend getaway, or a special event.
4.92 out of 5 average rating, 188 reviews
Downtown Lux Stay with Heated Pool (OPEN)
This HUGE luxury 5,000+ sq ft home is the perfect getaway. 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 (10 ft deep), 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!
4.98 out of 5 average rating, 129 reviews
TOP AIRBNB IN KETTERING! | Near Downtown Dayton!
Gorgeous, professionally remodeled home on a quiet street in Kettering -- located just minutes away from University of Dayton, Carillon Historical Park, Oakwood, and downtown Dayton. This home features a fully fenced in backyard, gourmet kitchen, completely new bathrooms, and so much more. If you are looking for an amazing, over-the-top, 5 star experience -- give us an opportunity!
4.98 out of 5 average rating, 212 reviews
Tiny Home fit for a King: Near Belmont Park!
Welcome to Tiny Home for a King, a stylish 472 sq. ft. retreat in Dayton perfect for solo travelers or couples. This thoughtfully designed space blends modern amenities with charming details, offering a cozy and comfortable atmosphere ideal for relaxing, recharging, or simply feeling at home. Everything you need for a memorable stay is right here in this tiny but inviting haven.
4.95 out of 5 average rating, 112 reviews
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!
4.99 out of 5 average rating, 143 reviewsPopular amenities for Oakwood vacation rentals
Other great vacation rentals in Oakwood

Relax close to Carillon Park
5.0 out of 5 average rating, 18 reviews
Comfy Colonial the heart of Kettering : 3BR, 1BA.
4.84 out of 5 average rating, 43 reviews
Comfy & Spacious Home : Near WSU/UD/WPAFB
4.89 out of 5 average rating, 19 reviews
*Cozy-Comfortable 2 Bedroom Kettering Apartment!*
4.72 out of 5 average rating, 94 reviews
Oregon District Luxury Stay- close to UD
5.0 out of 5 average rating, 21 reviews
5 min to UD, Fire Pit, Fenced Yard, No Airbnb Fees
4.98 out of 5 average rating, 53 reviews
Wedding & Holiday Season | Dayton 4BR Family HQ
5.0 out of 5 average rating, 42 reviews
Historic south park gem (close to UD, MVH & more)
4.97 out of 5 average rating, 37 reviewsDestinations to explore
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