Vacation rentals in Oakwood

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Top-rated vacation rentals in Oakwood

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Top guest favorite
A modern living area features a dark gray couch adorned with colorful pillows, paired with a mid-century chair. Natural light enters through two windows, illuminating the stylish rug while a round mirror reflects the space. A flat-screen TV is mounted on the wall, accompanied by a decorative console.
Home in Dayton
5 out of 5 average rating, 174 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.

Top guest favorite
Home in Dayton
4.94 out of 5 average rating, 221 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.

Guest favorite
A cozy sitting area showcases deep green and burgundy armchairs positioned near a wooden fireplace with intricate detailing. A small table holds decorative items, while bookshelves line the walls filled with various books. Floral wallpaper adds a touch of warmth to the space.
Home in Dayton
4.94 out of 5 average rating, 377 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.

Top guest favorite
A charming red-brick home is surrounded by lush greenery and colorful flower gardens. A stone pathway leads to the entrance, complemented by various potted plants. A small friendly dog is seen resting on the pathway, adding a welcoming touch to the serene outdoor space.
Guest suite in Dayton
4.93 out of 5 average rating, 163 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!

Guest favorite
An outdoor space features wooden lounge chairs arranged on green artificial turf. A wooden barrel sauna stands prominently, with a five-person hot tub nearby. Soft cafe lights hang overhead, creating a welcoming environment.
Home in Dayton
4.95 out of 5 average rating, 176 reviews

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.

Top guest favorite
A spacious living room is filled with natural light, featuring two comfortable sofas arranged around a coffee table. A large television is set on a dark wooden stand, while a decorative clock adds detail to the white brick fireplace. A floor lamp stands in a corner, providing additional lighting.
Home in Dayton
5 out of 5 average rating, 159 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!

Top guest favorite
A comfortable living area features a dark sofa adorned with decorative pillows and a cozy armchair. A round, tufted coffee table takes center stage, while a warm lamp provides soft lighting. The space is complemented by a patterned area rug and a framed map on the wall.
Apartment in Dayton
5 out of 5 average rating, 184 reviews

Take Flight

"Take Flight" is ready for you to enjoy during your stay in Dayton for work or play. Centrally located, this 2nd floor apartment is close to offices downtown, many nearby attractions, and main traffic arteries like I-75 and US 35. If you plan to stay in, Wi-Fi throughout the unit and a desk area in the bedroom can help you catch up on work. On the other hand, the 55" Smart TV, Blu-Ray player, books, movies and games are available if you'd rather relax.

Top guest favorite
A welcoming living space is highlighted by a sleek dark leather sofa and a cozy brown armchair. A modern coffee table sits in front, while warm lighting enhances the ambiance. The open kitchen area features stainless steel appliances and wooden cabinetry, with natural light streaming through the windows.
Bungalow in Dayton
4.94 out of 5 average rating, 219 reviews

South Park- The Purple Barney Guesthouse

Historic South Park Purple Barney guesthouse. Built in 1920 this shotgun cottage was rehabbed by me, a neighborhood activist, who stripped it down to the studs. What you'll find is a mix of historic, modern, and mid-century modern, with vaulted ceilings, skylights in both the bedroom and the spacious bathroom, and safe, snug, and quiet thanks to the insulation, new windows & doors. New Metal Roof in 2022! Your host is a Certified Service Disabled Vet.

Guest favorite
A spacious living area features a light-colored sofa and decorative cushions, arranged around a central round coffee table. Elegant artwork adorns the walls, and the room is illuminated by a modern chandelier. Window treatments offer privacy while allowing natural light to filter in.
Home in Dayton
4.91 out of 5 average rating, 175 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.

Top guest favorite
An inviting living area features a large brown leather sofa, a patterned area rug, and a decorative coffee table atop wide plank wood floors. A cozy corner chair and a lamp add warmth, while the back wall showcases a mural with 'Centerville Carriage.'
Guesthouse in Centerville
5 out of 5 average rating, 276 reviews

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.

Top guest favorite
Bungalow in Dayton
4.97 out of 5 average rating, 168 reviews

The Aviator Bungalow in Kettering

Our Aviator Bungalow in Kettering, Ohio is close to Carillon Park and University of Dayton. You will feel right at home with the amenities we offer. Our place is great for couples, solo adventurers, travelling nurses, doctors, therapists and business travelers. A nice city park is right across the street with a tennis court and basketball court, shelter and grill. Five minutes to University of Dayton/Downtown Dayton.

Top guest favorite
The exterior of Carillon Cottage features a striking blue facade with white trim, set against a backdrop of lush greenery. The structure displays a classic gable roof, with multiple windows allowing for natural light. A stone wall borders the front garden, which is accentuated by small, neatly trimmed hedges.
Home in Dayton
4.99 out of 5 average rating, 135 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!

Popular amenities for Oakwood vacation rentals

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  4. Montgomery County
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