House holiday rentals in Owensboro

4.95 out of 5 average rating, 340 reviews

The charming front porch is visible, featuring two red rocking chairs and a welcoming American flag. Lush green bushes frame the path leading up to the entrance, while a well-maintained yard provides a spacious outdoor feel. A bright blue sky complements the inviting atmosphere.

Home in Beaver Dam

Country Charm

This House is located in a quiet neighborhood one block off Main street here in Beaver Dam, KY. Enjoy a nice cozy country home while you visit. It is fully finished so you will feel right home. The property sits on a corner lot with access from both streets. The house has a front porch for lazy evening to catch some fresh air. You can pull right up underneath the carport for easy access to the back door for entry. The home offers a nice yard and fire pit. You are minutes from stores/ food.

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.

4.9 out of 5 average rating, 103 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).

4.97 out of 5 average rating, 104 reviews

A cozy living area is showcased, featuring a gray sofa adorned with patterned cushions. A wooden coffee table sits on a decorative rug, with a potted plant nearby. In the background, a partially visible kitchen area and art pieces add a touch of warmth to the space.

Home in Newburgh

RiverTown Retreat – Cozy 2BR Near River & Downtown

This is our personal home we use when lucky enough to be in the area. Our daughter married a sweet young man from here & we fell in love with this beautiful, friendly community and its adorable waterfront and downtown areas. We designed everything about this cottage to be exactly what we want & need, & we hope you appreciate all our thoughtful touches. Relax at this peaceful place to stay & enjoy Newburgh! Our location is also a great base for exploring Evansville, Owensboro, & Henderson.

A single-story home with a brick facade is presented. The driveway leads to a garage, while a well-maintained lawn features neatly trimmed grass and colorful flowerbeds. Large front windows allow for natural light, framed by light-colored siding underneath a gabled roof.

4.93 out of 5 average rating, 123 reviews

Bluegrass Commons

You will be close to everything when you stay at this centrally-located three bedroom two bath home right off the bypass that is a short drive to anywhere in Owensboro, KY for any business travelers. This is a brand new construction home in Bluegrass Commons neighborhood! New furnishings and the home sleeps 6 comfortably. Split bedroom with an open concept perfect for families. Fully stocked kitchen with a keurig coffee station. Large backyard perfect for entertaining or just grilling.

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.

5 out of 5 average rating, 180 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.

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.

4.94 out of 5 average rating, 174 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.

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.

4.99 out of 5 average rating, 168 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.

Home in Downtown Evansville

An open living area showcases original exposed brick walls and modern amenities. A spacious kitchen island is paired with stainless steel appliances. The living space features a sectional couch facing a large projector screen, with ambient lighting provided by pendant fixtures.

4.96 out of 5 average rating, 228 reviews

Rooftop Views in the Heart of Downtown!

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. Dr. Mitchell's owners' quarters above the original animal clinic now features two bedrooms, an open bunk room for kids, and three full bathrooms. You'll find the original exposed brick throughout the home which adds the perfect vibe to this modern industrial home.

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.

4.98 out of 5 average rating, 177 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.

4.85 out of 5 average rating, 161 reviews

The Bluegrass Barbie

Welcome to Owensboro, KY home to the ONLY Bluegrass Museum Hall of Fame on PLANET EARTH! Minutes away from Owensboro Convention Center, ALL sports facilities, world class dining, & one of the MOST UNIQUE stays in Owensboro, KY! Great home to stay at for sports tournaments, visiting family, visiting Holiday World, or just a weekend away! And don't forget to check out The Green River Distillery!

4.95 out of 5 average rating, 251 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.

A living room features hardwood floors and blue accent walls. Comfortable seating is provided by a sofa and two chairs, with a patterned area rug at the center. Natural light enters through a large window, and a fan hangs from the ceiling, enhancing the space's openness.

4.9 out of 5 average rating, 184 reviews

The Cabin in Town

The Cabin in Town is recently remodeled home from the 1950s with hardwood floors and original trim work. The house is centrally located in town on a nice quiet street and ready to receive guests. ****** 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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The outdoor pool area features a spacious blue swimming pool surrounded by lounge chairs and an umbrella. A vibrant pink mural decorates the surrounding wall, with lush greenery providing a natural backdrop. A pool float is visible in the water, enhancing the inviting atmosphere.

5 out of 5 average rating, 8 reviews

The Pink Limozeen

The exterior of a brick home is presented, featuring a pitched roof and multiple windows with white shutters. Neatly trimmed hedges and trees are arranged in the front yard, accompanied by a well-maintained lawn and a subtle walkway leading to the entrance.

Home in Henderson

Golf Course and Pool!

A welcoming brick home is set against a backdrop of lush greenery, featuring a spacious driveway leading to a two-car garage. Large windows provide natural light, and the front yard is landscaped with well-maintained grass and mature trees.

4.83 out of 5 average rating, 18 reviews

Pool Is Open! Waterslide!Fun!Home Away From Home!

An aerial view of the inground pool, showcasing its vibrant blue water surrounded by a spacious patio. The area includes landscaped greenery, a wooden bench, and a shaded umbrella, inviting relaxation in a serene outdoor environment.

4.98 out of 5 average rating, 65 reviews

Blue Moon Cottage: Music Room, Inground Pool

A stone monument sign is prominently displayed, marking the entrance to Victoria National Golf Club. The sign, featuring the word 'Victoria' in large lettering, is surrounded by lush greenery and open space under a partly cloudy sky.

Home in Newburgh

Victoria National Golf Course Bungalow 4BR/3Bath!

Superhost

New place to stay

Perfect for relaxation and work+100% cotton sheets

Superhost

A spacious living area is highlighted by a decorative fireplace with a round mirror above it. A modern ceiling fan hangs overhead, while a glass coffee table sits on an area rug. A compact desk and television unit are also visible, contributing to a warm atmosphere.

4.81 out of 5 average rating, 36 reviews

Bluegrass Getaway • Swim, Relax & Unwind

The image displays various areas of a spacious vacation home. A bright kitchen is seen with modern appliances and ample counter space. A cozy dining area accommodates multiple guests. Outside, a hot tub offers relaxation, and an outdoor patio with seating is visible, surrounded by greenery.

5 out of 5 average rating, 37 reviews

Hot Tub /Pool/Fire Pit & BBQ

Weekly house rentals

Superhost

A single-level home is featured with a welcoming front porch swing, framed by greenery. The entrance includes a ramp, allowing for easy access. The yard includes a pathway that leads to the front door, enhancing the welcoming atmosphere of the residence.

Home in Sacramento

4.71 out of 5 average rating, 14 reviews

CROSSROADS COTTAGE

5 out of 5 average rating, 30 reviews

A peaceful countryside scene features rolling hills and a clear pond surrounded by trees. Bare branches indicate the changing seasons, while a vibrant blue sky is dotted with soft clouds, creating a serene backdrop of nature.

Home in Olaton

Cowbell Cottage farm stay

5 out of 5 average rating, 32 reviews

A charming house stands amidst tall trees, softly illuminated by outdoor lighting in the evening. The two-story structure features a spacious deck and large glass doors, blending seamlessly with the surrounding woodland. A gravel path leads up to the entrance, enhancing the tranquil setting.

Home in Webster County

Newly Listed! Secluded 3 BR house in the Woods!

4.93 out of 5 average rating, 30 reviews

A dining area is presented with a round wooden table and two upholstered chairs. A large wall-mounted television is positioned near a dark wooden console that holds decorative items. Natural light filters through sheer curtains, illuminating the warm-toned flooring.

Home in Newburgh

Walking The River

5 out of 5 average rating, 95 reviews

An outdoor fire pit area is surrounded by six wooden Adirondack chairs, creating a cozy gathering spot on a grassy lawn. The former church building is visible in the background, framed by trees and bathed in natural light.

Home in Grandview

The Storehouse - unique retreat near Holiday World

4.9 out of 5 average rating, 52 reviews

The exterior of a charming light blue house is shown, featuring white shutters and a welcoming front porch. A decorative wreath adorns the door, while pink ornamental grasses frame the yard, adding a pop of color to the peaceful setting.

Home in Rockport

Near Holiday World & Owensboro, The Little House

A single-story brick home with a brown, shingled roof is set against a clear blue sky. Lush green shrubs frame the entrance, and a manicured lawn leads to a two-car garage. A small decorative figure is positioned near the flowerbed, adding a subtle touch to the exterior.

4.98 out of 5 average rating, 42 reviews

Horse Haven at the Heartlands

5 out of 5 average rating, 40 reviews

The exterior of the cottage showcases a welcoming blue facade with white trim. A covered porch features a comfortable swing, and large windows provide ample natural light. Lush green trees frame the peaceful setting, enhancing the cottage's serene ambiance.

Home in Henderson

Little House on the River

Private house rentals

A welcoming living area features a comfortable sectional sofa adorned with decorative pillows. A sleek coffee table occupies the center, while a modern television is positioned across from the seating. Soft lighting is provided by a ceiling fan, and large windows dressed in dark curtains allow natural light.

4.97 out of 5 average rating, 90 reviews

House Near U of Evansville and Ford Center

A single-story home with a light green exterior features dark blue shutters and a welcoming front door. A small porch leads to the entrance, surrounded by well-maintained flower beds, and a grassy yard extends to the front, under a clear blue sky.

5 out of 5 average rating, 20 reviews

Green Oasis

4.99 out of 5 average rating, 72 reviews

Historic Haynie's Corner Hideout

Aerial view of a spacious home surrounded by lush greenery and a serene lake. The property features a well-maintained lawn, a circular driveway, and a wooden fence. Nearby homes are visible along the waterfront, enhancing the sense of a peaceful community.

5 out of 5 average rating, 12 reviews

Lakeview Home by the Ball Fields

The exterior of the Hobbit House features unique architectural elements, including curved rooflines and a distinctive round window. A manicured pathway leads to the front door, with greenery surrounding the entrance and decorative outdoor lighting providing subtle illumination.

4.97 out of 5 average rating, 94 reviews

Hobbit House 2 bedroom.

A cozy living area features a brown sofa and two armchairs, arranged around a low coffee table on a large area rug. Large windows are draped with dark curtains, allowing natural light to brighten the space, complemented by a standing lamp and decorative artwork.

4.98 out of 5 average rating, 50 reviews

Northside newly updated, 2 beds!

4.97 out of 5 average rating, 60 reviews

A charming blue cottage is depicted, featuring a covered entryway and multiple awnings. Lush greenery surrounds the home, while a concrete pathway leads toward the entrance. A neighboring white building is visible in the background, set against a clear blue sky.

Home in Beaver Dam

The Bluegrass Cottage, Downtown Beaver Dam, KY

A cozy living room features a tan sofa facing a white fireplace, surrounded by natural light from multiple windows. A patterned area rug adds warmth to the space, while a small side table complements the seating. An open passage leads to the kitchen area.