
Vacation rentals in Owensboro
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Top-rated vacation rentals in Owensboro
Guests agree: these stays are highly rated for location, cleanliness, and more.

Private Guest House close to everything!
The Private Guest House is set on our property which is located on a corner (1.5 acre lot) close to the east side of Evansville. The convenient large circle drive makes it easy to enter and exit. The east side of Evansville offers Malls, Shopping, Restaurants, Bars, Entertainment, Gyms, Starbucks, and Theaters. The property is located only 10 minutes from Downtown and the Ford Center due to close proximity to Lloyd Expressway. Check out the Casino and Riverfront if you’re in the Downtown Area!

The Woodford Retreat Cottage
Take it easy at this unique getaway.. Completely renovated 2,000 sq ft home with a beautiful river view, 3 bedrooms, 2 family rooms, 2 full bathrooms, fully stocked kitchen. The back yard is fenced with a deck, patio table and glider. This property is located a few blocks from the Owensboro Convention Center, Bluegrass museum, and multiple downtown restaurants. This property adjoins English park. Excellent rental for a weekend of downtown adventures or just enjoying the river view.

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.

Crouse’s North Ninety Lake House
If you want a place where you can be socially distanced, this is the place! (discounts for weekly or monthly stays.) The cabin is set in a 90 acre area surrounded by woods with two small lakes (fishing, walking trails and paddle boating available at no extra charge). There is only one other cabin on the 90 acres. Nearest town, Dixon (3 miles), Madisonville (20 miles, Henderson 21 miles), Evansville, IN (has a regional airport about 35 miles). Truly a relaxing getaway place.

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.

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.

Hattie's Hill Cottage
Cottage sits behind our home (see photo). NOTE- Main house may have large groups. Pool and outside areas share spaces. Near Owensboro, Rockport, Hawesville & Lewisport. There is ONE bedroom which can be made into EITHER two California twins OR one California king -Wifi. We have a Smart TV you may use your Netflix and so on with. Kitchen is well stocked with necessities. Eating/work space is provided. Comfortable recliner chairs. Access to the grounds.

Handcrafted Cabin in Woodsy Heaven
PLEASE read listing before booking. Custom built wood cabin nestled in the rolling hills of western Kentucky. Cozy decor with vintage theme, handcrafted wood floors, and outdoor space overlooking wooded property. Rustic studio space full of modern amenities. Close proximity to 5450 acre Wildlife Management Area with hiking, horseback riding, fishing, hunting, and swimming. Perfect location to get back to nature. Great peaceful weekend or overnight getaway.

Nature Lovers Retreat
This charming cottage is the perfect getaway for nature lovers. Relax in this home’s cheerful and cozy atmosphere, located on the edge of Ben Hawes Park with over 4 miles of beautiful walking trails and 7.5 miles of bike trails in this gorgeous 297 acre forest. Enjoy all the comforts of home, including free WiFi, TV, washer and dryer, full kitchen, and free parking. This special retreat is also only 1 mile from Ben Hawes Golf Course.

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.

Riverfront Loft Above Honey Moon Coffee Shop
Located right on the riverfront in downtown Newburgh. Perfect access for walking, hiking, running, or bike riding on the popular riverfront trail. With epic views of the Ohio River including a 2nd story balcony view of beautiful sunrises and sunsets, our stylish loft apartment is located directly over Honey Moon Coffee shop. 2 complimentary drip coffees are included with your stay.

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.
Popular amenities for Owensboro vacation rentals
Other great vacation rentals in Owensboro

Hill Ave home

The Farmers Loft- Second floor

Green River Getaway

TheeHeirloom+Historic Venue&Home

A Cozy Kentucky Retreat w/ Fishing and boating

Heartland Hideaway

Rustic Log Cabin Old Farm

The Nest
Quick stats about vacation rentals in Owensboro
Total rentals
130 properties
Nightly prices starting at
R695 ZAR before taxes and fees
Total number of reviews
7.9K reviews
Family-friendly rentals
90 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
10 properties have a pool
Frequently Asked Questions
Are there pet-friendly vacation rentals in Owensboro?
Four-legged friends are welcome in Owensboro. Choose from more than 50 vacation rentals for guests traveling with pets.
Do apartment rentals in Owensboro have a kitchen?
Absolutely! We offer over 20 apartment rentals with a kitchen in Owensboro. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Owensboro?
Yes! Work meets play with ease at over 50 vacation rentals in Owensboro featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Owensboro have wifi?
Absolutely! We offer over 70 house rentals with wifi in Owensboro. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Owensboro?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 20 homes with a kitchen, over 20 homes with wifi, over 20 homes with free parking, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do apartment rentals in Owensboro have air conditioning?
Absolutely! We offer over 20 apartment rentals with air conditioning in Owensboro. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Owensboro have free parking?
Absolutely! We offer over 20 apartment rentals with free parking in Owensboro. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Owensboro?
Owensboro has more than 80 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
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