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

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

4.94 out of 5 average rating, 211 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!

ValueFamilyPets

Top guest favourite

Home in Dayton

4.94 out of 5 average rating, 223 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.

FamilyValueHospitality

Guest favourite

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, 383 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.

ValueFamilyBreakfast

Guest favourite

The exterior of a blue cottage is seen, highlighted by white hydrangeas and greenery in the foreground. Large windows allow natural light to enter, and trees offer shade nearby. The inviting facade features decorative elements at the peak of the roof.

Home in Dayton

4.91 out of 5 average rating, 104 reviews

Little Boy Blue - Southpark’s 2BR Cottage withWIFI

Our peaceful and centrally-located cottage is walking distance to UD, MVH, Oregon District and Downtown. Relax in house with spacious Living, Dining, Kitchen and Bathroom or enjoy our backyard, fire pit included. There are two simple bedrooms: queen bed with 2 closets in the main; full bed in the other. Washer & dryer in basement. The living room has a 50” Samsung smart TV & WiFi! We recommend the local coffee, restaurants, local breweries and learn some Dayton history! *Key pad access.

LocationValueKitchen

Superhost

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

4.93 out of 5 average rating, 182 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.

ValueLocationDecor

Top guest favourite

The airy living room features an oversized couch, a mounted TV, and two blue armchairs. Natural light enters through large windows, highlighting the hardwood flooring. A door leads to a spacious backyard, while a light fixture provides soft illumination.

Home in Dayton

4.99 out of 5 average rating, 168 reviews

Cozy Beach House Minutes From Dayton!

Welcome and enjoy your trip in one of Dayton's best neighborhoods! Minutes from Dayton and a quick drive to the university. There is so much available at your fingertips. Wake up and grab a coffee at Warehouse 4. Stop by Trader Joes or Kroger to get your groceries. Take a walk through the many amazing parks nearby or catch a concert at Fraze Pavilion. After a day out, relax in the living room and watch your favorite shows or movies. Make yourself at home and live like a Dayton local!

ValueFamilyGrill

Superhost

Home in Dayton

4.87 out of 5 average rating, 126 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.

ValueFamilyLaundry

Top guest favourite

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, 224 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.

ValueLocationIndoor spaces

Top guest favourite

The front entrance features a welcoming porch with a red door and a stone stoop. Potted plants hang from the eaves, accented by well-maintained landscaping that includes lush greenery and mulch beds. Windows frame the entrance, providing a bright and inviting appearance.

Home in Dayton

5.0 out of 5 average rating, 17 reviews

Relax close to Carillon Park

Located close to downtown, UD and UD Arena, Carrillon Park, and Kettering! All the amenities and more! Only a 15 minute drive to Wright Patterson AFB and Beavercreek! There's a front porch and back porch to enjoy the quiet mornings and evenings! Enjoy the spacious bedrooms and bathrooms, beautiful kitchen, and dining area! Plenty of blankets and extra linens that are soft and cleaned!

FamilyLocationLaundry

Top guest favourite

A two-story home features a dark exterior complemented by white trim. A landscaped front yard includes a walkway leading to the entrance. Surrounding trees provide shade, and neighboring homes are visible in the background. A fenced backyard can be seen to the side.

Home in Dayton

4.98 out of 5 average rating, 209 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!

LocationFamilyOutdoor spaces

Top guest favourite

The exterior of the tiny home is showcased, featuring a dark green wooden facade. A single door with six panels stands prominently, complemented by a small window. Planters with greenery are positioned beside the entrance, and a wooden deck extends from the front, partially covered by snow.

Home in Dayton

4.95 out of 5 average rating, 108 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.

ValueFamilyWalkability

Top guest favourite

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, 139 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!

FamilyValueAir conditioning