Holiday rentals in Oakwood

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Top-rated holiday rentals in Oakwood

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Bungalow in South Park
4.96 out of 5 average rating, 348 reviews

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.

Guest favourite
An open concept kitchen is highlighted, featuring a large black island with modern chairs. Stainless steel appliances and a stylish backsplash complement the sleek cabinetry. Natural light streams through the windows, illuminating the airy dining area in the background.
Home in South Park
4.94 out of 5 average rating, 204 reviews

TOP AIRBNB IN DAYTON! | SOUTH PARK | FENCED YARD

Stunning Three Bedroom Historical South Park bungalow - located just steps away from UD, downtown Dayton, and Miami Valley Hospital. This home features an open concept living space with white oak hardwood flooring through-out. The kitchen is fully equipped with all the modern amenities: stainless steal appliances, soft close cabinetry, granite countertops. Two Gorgeous bathrooms w/ custom tile work including a master w/ walk-in shower. Completely fenced in rear yard w/ privacy. Magical space!

Top guest favourite
A welcoming living room features a black couch, two light-colored club chairs, and a coffee table on a woven rug. Natural light fills the space through large windows adorned with white drapes. A decorative mirror and side table enhance the room's charm.
Home in Dayton
4.95 out of 5 average rating, 207 reviews

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!

Top guest favourite
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 South Park
5 out of 5 average rating, 169 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 favourite
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.

Top guest favourite
A striking blue exterior is complemented by a bright yellow door, creating a vibrant entrance. A large window beside the door allows natural light to illuminate the space within. The setting is accented by nearby greenery and a concrete path leading to the entrance.
Home in South Park
4.98 out of 5 average rating, 208 reviews

Oak Street Place in Historic South Park District

This is a one of a kind stay located in the heart of the historic South Park district. This unique property used to serve as several different types of businesses including a barbershop, grocery store and church. The space has now been completely remodeled into a stunning open concept home full of history and character. With ship lap walls and vaulted ceilings with original exposed beams, it looks like it could have been on an episode of HGTV’s Fixer Upper! Come stay at Oak Street Place!

Top guest favourite
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, 158 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 favourite
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 South Park
4.95 out of 5 average rating, 173 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 favourite
A cozy living area is presented with hardwood flooring and neutral-colored walls. A flat-screen television is positioned near a window with sheer curtains. A small plant adds a touch of greenery beside a comfortable couch, complemented by an accent chair and side table with a lamp.
Flat in Dayton
4.92 out of 5 average rating, 130 reviews

Root2Rise Quiet, Clean, Prime Location, 2 bedroom

Enjoy your own two-bedroom, first floor apartment in a quiet four-unit building. It is modestly decorated, squeaky clean and cozy. This location could not be more convenient! Walking distance to two grocery stores, retail shopping, and The Fraze Pavilion. Ten minute drive to Kettering Hospital, Miami Valley Hospital, downtown Dayton and University of Dayton. 15-20 minute drive to the Wright Patt Air Force base. Furnished and equipped with everything you need.

Top guest favourite
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, 155 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 favourite
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 South Park
4.92 out of 5 average rating, 167 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.

Superhost
The living area features two spacious sofas positioned around a central coffee table. A large flat-screen television is mounted on a light-colored wall, above a decorative fireplace. Natural light enters through large windows, enhancing the inviting ambiance of the room.
Home in Dayton
4.82 out of 5 average rating, 184 reviews

★ Trendy Spot Located in an A+ neighborhood

Welcome to Kettering! This beautiful 3 Bedroom 2 Bath home offers guests a private getaway with the whole house to yourself. Conveniently located nearby malls, restaurants, while still being secluded in a great neighborhood. Nearby Destinations: The Fraze - .6 Miles Kettering Medical Center 1.7 Miles Oregon District - 3.5 Miles University of Dayton - 3.5 Miles Downtown Dayton - 5 Miles Easy Access to I-35 and I-75

Popular amenities for Oakwood holiday rentals

  1. Airbnb
  2. United States
  3. Ohio
  4. Montgomery County
  5. Oakwood