House holiday rentals in Owensboro

Find and book unique houses on Airbnb

Top-rated house rentals in Owensboro

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

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The exterior of a single-story home features light gray vinyl siding and a dark gray roof. White window shutters complement the windows, and a covered porch is positioned at the entrance. A grassy lawn surrounds the house, with a clear sky and scattered clouds above.
Home in Owensboro
4.84 out of 5 average rating, 243 reviews

Emma B's Place Close to Town and the Riverfront

Emma B's Place is newly renovated and ready for guests! Here you'll find a cozy atmosphere, comfortable beds, fully equipped kitchen, and brand new washer & dryer. The location is convenient to an award winning Riverwalk, shopping, great dining, and our central location offers a short commute to the entire city. If you prefer to stay in and relax, a 42-inch smart tv and wireless high-speed internet are available for your enjoyment. Lockbox self-entry. Your hosts live nearby if you need anything!

Guest favourite
A spacious living area is furnished with a large sectional sofa, complemented by decorative pillows. A ceiling fan provides airflow, while natural light filters through the window blinds. A guitar hangs on the wall, and a wall-mounted artwork adds a pop of color.
Home in Owensboro
4.91 out of 5 average rating, 110 reviews

The Bluegrass House

Welcome y'all! Serene hot tub, fenced-in back yard (2-dog limit, extra charge). Airport shuttle (separate fee). Nestled near parks, 3 miles from Edge Ice/Sports Arena. Immerse yourself in cultural richness at Bluegrass Music Hall of Fame and Owensboro Symphony Orchestra. Enjoy free summer outdoor entertainment on the Riverfront. Holiday World (30+min). Experience southern style with breakfast at Windy Hollow Biscuit House, & ribs, mutton or burgoo at Moonlight BBQ (visited by celebrities).

Top guest favourite
A cozy living area features a brown leather sofa paired with a plush cream-colored armchair. A large patterned rug anchors the space, while a wooden coffee table provides a functional centerpiece. An acoustic guitar leans against the armchair, adding a creative touch.
Home in Evansville
4.98 out of 5 average rating, 271 reviews

Haynie's Hangout

Haynie’s Hangout was featured in Evansville Living. Located in the Art's District and within walking distance of restaurants. Ideal for business travel. Spacious desk for work needs. Very close to downtown attractions. Charming two bedroom shotgun home with stylish and hip decor. All bedding is high quality. Cozy living room with large smart TV/LG and internet access for Netflix, etc. Leaf antenna provides local TV channel access. Equipped kitchen! Washer/Dryer. Patio! Photo ID required.

Top guest favourite
A charming home with white siding and a pitched roof is showcased. The front entrance features a yellow door, flanked by two black chairs. Green grass and neatly trimmed shrubs create a welcoming atmosphere along the stone pathway leading to the entrance.
Home in Newburgh
4.96 out of 5 average rating, 142 reviews

Little Monticello

Little Monticello is a spacious 3 bedroom home one block away from the beautiful river front. Great walking paths. Walking distance to downtown Newburgh dining and shops. The master bedroom has a king size bed , bedroom # 2 has a queen size bed and dressing table. Bedroom #4 has a full size bed.. Bedrooms 1&2 have TV’s in them. The side porch is great for relaxing or hanging out with the little ones. There is a full size washer and dryer located in the kitchen area behind the barn door.

Top guest favourite
An open concept living area features a plush gray sofa with accent pillows, complemented by a modern coffee table on a textured area rug. The kitchen area includes wooden cabinets and bar seating, while natural light brightens the space through a nearby window.
Home in Owensboro
5 out of 5 average rating, 181 reviews

4bed3BR Near Conv Ctr/Fisher Pk/30to HolidayWorld

METICULOUSLY CLEAN, updated 3 bedroom home, 4 beds each with tv, private Home is 3 miles from Convention center, River Park Center, Bluegrass Museum, Science Museum, Botanical Garden. It’s also minutes from baseball fields (Fischer) 30 min to Holiday world, private and fenced backyard with lighted patio. Home is well stocked with ALL you may need! If the home is empty previous night, early check in, no charge! - Wifi - Roku TV in all bedrooms - Washer and Dryer - Stocked kitchen.

Guest favourite
The exterior of the Cozy Cottage is presented, showcasing a two-story structure with blue shutters and flower boxes. A set of wooden stairs leads to the entrance, which is framed by a tree that provides shade. The surrounding yard features green grass and a pathway.
Home in Owensboro
4.95 out of 5 average rating, 184 reviews

The Cozy Cottage

Join us for a relaxing stay at the Cozy Cottage! Inside you will find everything you need to make for a cozy stay whether you’re with us for short weekend or a month. Outside you will find plenty of spaces to sit and enjoy the view of the Ohio River just 2 blocks away. The Cozy Cottage is conveniently located less than 5 minutes from downtown Owensboro and popular attractions such as the Convention Center, Bluegrass Museum, Botanical Gardens, and Jack C. Fisher Park.

Top guest favourite
An open-concept living area is highlighted by exposed brick walls and wooden flooring. A comfortable seating arrangement includes a sofa and two chairs, inviting relaxation. The kitchen features modern appliances and a breakfast bar with stools, with natural light streaming through large windows.
Home in Downtown Evansville
4.93 out of 5 average rating, 106 reviews

Downtown Haven Retreat

Welcome to the Dr. J.R. Mitchell House! Built in 1909 as what is believed to be the first animal clinic in Evansville, this century-old home has been renovated and modernized. This downstairs apartment was Dr. Mitchell’s original animal clinic while his family’s quarters was located upstairs. Inside, you’ll discover urban comfort at our 2 bed, 2 bath apartment and be just steps away from shopping, dining, and all that the downtown riverfront area has to offer.

Top guest favourite
A spacious living area features a large flat-screen television mounted on a dark wall. Two light gray sofas are arranged around a round coffee table on a textured rug. Soft lighting from two side tables complements the warm wooden flooring.
Home in Owensboro
4.99 out of 5 average rating, 175 reviews

Midtown Cottage- Self Check-In & Centrally Located

Enjoy your stay in Owensboro, KY in this cozy, warmly decorated home! This home is centrally located to everything Owensboro has to offer, a short drive from downtown and the award winning riverfront. Wifi and parking are included. Enjoy a stylish experience at this centrally-located home. You will enjoy relaxing either in the home or the lovely backyard space. Whether you are in town for work or play indulge in the comfort and tranquility of this modern house.

Guest favourite
A single-story home with a light blue exterior sits in a quiet neighborhood. The well-maintained front yard features small shrubs and landscaping, while a paved driveway provides easy access. Trees in the background showcase autumn colors, enhancing the peaceful environment.
Home in Evansville
4.87 out of 5 average rating, 102 reviews

Kozy Kathleen

*Currently listed as top 10 AirBnbs in Evansville, IN. *Kozy family home in a quite neighborhood with 2 car capacity drive way including street parking if necessary. *Full of amenities needed for any length of stay. Close to I-69 and HWY 41 for any travel requirements. *Less than 5 miles from the heart beat of Evansville (Ford center/ downtown/ and Eastland mall). *"The Kozy Kathleen" = Real Hoosier home with authentic mid-west feel.

Top guest favourite
A tidy living room showcases a plush, purple sofa and a cozy armchair, accompanied by a decorative lamp and coffee table. A white fireplace serves as a focal point, while natural light filters through the window coverings, creating a welcoming ambiance.
Home in Owensboro
4.98 out of 5 average rating, 179 reviews

Granny Smith's

Granny Smith's is an endearing home in the heart of Owensboro, located in a historic neighborhood. The house features one sizable bedroom, tidy living room, full kitchen, cozy dining area, and a tub/shower bathroom. There is also relaxed outdoor living areas either on the front porch or back screened in patio. Property also has a small detached carport with a driveway. There is also parking on the street.

Top guest favourite
Home in Owensboro
4.95 out of 5 average rating, 264 reviews

2 bedroom w/free on-site parking. Near downtown

When you stay at this centrally located accommodation, your family will be close to everything. The backyard is fenced in and has a fire pit. The sofa has one pullout bed. The master suite has one queen bed. The second bedroom has two XL twin beds. Complete kitchen with dishwasher, plates, utensils, and washer and dryer. No more than two pets. Pets must be under 30 pounds each.

Guest favourite
A cozy living area features a mix of comfortable seating, including two blue armchairs and a leather sofa. A patterned area rug sits on polished wooden flooring. A dining area is visible in the background, illuminated by natural light from the window.
Home in Owensboro
4.89 out of 5 average rating, 269 reviews

Brick Bungalow

1150 Sq Ft House, two bedrooms with queen beds, office, separate dining area in quiet neighborhood in the center of town. We do allow pets for an additional one-time fee (per visit)of $45 paid through Airbnb. No more than two dogs and we ask that animals not sleep or be on the beds. Thank you!

Popular amenities for house rentals in Owensboro

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Avg. price$145 SGD$159 SGD$159 SGD$163 SGD$165 SGD$169 SGD$173 SGD$165 SGD$163 SGD$158 SGD$159 SGD$159 SGD
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Quick stats about house rentals in Owensboro

  • Total holiday rentals

    Explore 80 holiday rentals in Owensboro

  • Nightly prices starting at

    Owensboro holiday rentals start at $89 SGD per night before taxes and fees

  • Verified guest reviews

    Over 5,850 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    80 of Owensboro holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Owensboro rentals

  • 4.9 Average rating

    Owensboro stays are highly rated by guests – averaging 4.9 out of 5!

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