Home Vacation Rentals By Owner In Owensboro, KY

Showing 37 Of 37 Vacation Rentals
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Exceptional(3)

$94.49

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Private Vacation Home

Cozy, Furnished Corporate Rental

Owensboro, Kentucky, United States

Travel, Medical Pros and Corporate Rental Friendly! Welcome to this adorable 2 Bedroom 1 Bath Home. Near Legion Park, KWC, Brescia University, Owensboro Health and minutes from shopping, dining and the downtown Riverwalk. brbrSay Goodbye to impersonal hotels and spread out in this adorable, furnished home with new furnishings and amenities. Room to work, rest and play!brbrComing to Owensboro for an extended period We offer short/long term flexible pricing. We're looking forward to your stay!
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$355.75

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Private Vacation Home

Luxe Retreat Home @ Griffith Ave – Prime Location! ➠ 524W

Owensboro, Kentucky, United States

THE TRUE NORTH presents… Luxe Retreat Home @ Griffith Ave – Prime Location! ➠ 524WbrbrWelcome to your ultimate group getaway, just 1.2 miles from downtown! This stylish and spacious home comfortably sleeps up to 10 guests and combines convenience, comfort, and modern design. Perfect for family reunions, golf trips, wedding groups, or extended stays, it's the ideal base for exploring everything the area has to offer.brbrSoak up relaxing evenings on the private patio, cook together in the fully equipped kitchen, or unwind in the cozy living room after a day downtown. Every detail is designed with your comfort in mind.brbr HIGHLIGHTS br ️ Sleeps 10 Guests – Perfect for families, groups, and gatheringsbr 4 Bedrooms + Sleeper Sofa – Three large bedrooms + bunk room + extra sleeping spacebr Fully Equipped Kitchen – Everything you need to cook, dine, and gatherbr Fast Wi-Fi + Smart TVs – Stream, work, and stay connected with easebr Garage + Parking – Secure carport and large driveway for multiple vehiclesbr Private Patio + Backyard – Relax and enjoy peaceful outdoor spacebr Washer & Dryer – Convenient laundry on the main levelbr☕ Starter Supplies Provided – Coffee, creamer, soap, detergent, paper goodsbr Pets allowed (charges apply per pet)brbr LIVING AREAbrKick back and relax in a bright, open living space featuring comfy seating, a smart TV, and plenty of room to unwind after exploring downtown. The sleeper sofa adds flexibility for larger groups, while the layout ensures everyone can gather together comfortably.brbr ️ KITCHEN & DININGbrThe modern, fully stocked kitchen has everything you need to cook and connect—including a full-size fridge, oven, stove, microwave, dishwasher, and coffee maker. Whether you're preparing family breakfast or late-night snacks, you'll have all the essentials at your fingertips.brbrThe adjacent dining area easily seats your group, creating the perfect setup for shared meals and conversation.brbr ️ BEDROOMS & BATHROOMSbr ️ Bunk Room: 1 Bunk bedbr Bedroom 1: 2 Double Bedsbr Bedroom 2: 1 Queen Bedbr Bedroom 3: 2 Double Bedsbr​​​​​​​br ️ Living Room: Includes a sleeper sofa for additional sleeping spacebr Bathrooms (2 full) – Bright, clean, and fully stocked with essentialsbrbr OUTDOOR SPACEbrStep outside to enjoy your private patio and backyard, perfect for coffee in the morning or wine in the evening. The quiet residential location offers a relaxing atmosphere, while the secure garage and ample parking make arrival easy and worry-free.brbr LOCATION ADVANTAGESbr 1.2 miles from downtown—easy access to shopping, dining, and entertainmentbr Close to great local restaurants and cafesbr Near Griffith Avenue for convenient routes and quick access to area attractionsbr Peaceful neighborhood setting—enjoy the best of both worlds: quiet and close to everythingbrbr OTHER THINGS TO KNOWbr✨ Starter amenities provided: dish soap, Tide pods, coffee, creamer, sugar, toilet paper, paper towels, and bath towelsbr Fastest available Wi-Fi for streaming and remote workbr Guests have exclusive access to the entire home, backyard, patio, and garagebrbr READY TO MAKE MEMORIES brThis home is the perfect blend of space, comfort, and location—designed for families, friends, and groups looking to stay near it all. Book your stay with THE TRUE NORTH and experience your next unforgettable getaway.
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Exceptional(1)

$160.9

/ Nightly
Private Vacation Home

Cozy Cottage home

Owensboro, Kentucky, United States

When you stay at this centrally accommodation, your family will be close to everything. The backyard is fenced in and has a fire pit. The sofa has one pull out bed. The master suite has one queen bed. The second bedroom has two XL twin beds. Complete kitchen with dishwasher, plate's, utensils, and washer and dryer. No more than two pets. Pets must be under 50 pounds each
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Sleep 6

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Exceptional(38)

$203.94

/ Nightly
Private Vacation Home

Quiet neighborhood/2 car garage/fire pit/backyard privacy fence/PET FRIENDLY

Owensboro, Kentucky, United States

Located close to the Downtown Convention Center/Ballparks/Golfing/ and Colleges. Safe neighborhood to walk/jog. Enjoy the private backyard/parking your car in the garage. This is a Home Away From Home
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Exceptional(15)

$137.59

/ Nightly
Apartment

Private 1 bdrm apartment in the heart of the city. Pet friendly.

Owensboro, Kentucky, United States

Built in 1916 in the heart of the city, this private apartment has easy access to all the main arteries in town and less than .5 miles of all amenities you may want. One bedroom, one bathroom apartment. Fully stocked kitchen with washer and dryer. Pet friendly (no fenced yard). Apartment is attached to another unit (2 bedroom), connected with a locked door. Message me for information on renting both units.
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$274.42

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Private Vacation Home

Blue Moon Cottage: Historic Owensboro Home w/ Pool, Music Room, Location

Owensboro, Kentucky, United States

Welcome to Blue Moon Cottage, a charming home nestled in the heart of Owensboro, that offers a lovely blend of vintage allure and modern comfort. Built in 1935 and recently remodeled, this historic home exudes both character and contemporary elegance. brbrRelax by the pool and cozy outdoor seating area, or indulge in the beautifully decorated interiors which includes a room dedicated to bluegrass music, a musical genre that originated in this area.brbr** New roof and siding in 2025. Updated photos coming soon!brbrMain floor —brMaster bedroom w/ dresser, king bedbrLaundry room w/ washer, dryer, iron, ironing board, steamerbrMaster bathroom w/ walk-in dual shower & large whirlpool tubbrMusic room w/ futon, Bluetooth/vinyl record player, bluegrass album collection, guitar & mandolinbrLiving room w/ 55 4K smart tv, gas fireplace & large sectional sofabrDining room w/ seating for 6brKitchen (fully-stocked) w/Jenn Air gas stove/double oven, Whirlpool fridge w/ ice & water dispenser, Keurig Dual coffee maker (pods & carafe)brbrUpstairs—brBedroom 2 w/ king bed, vanity, dresser & walk-in closet brBathroom 2 w/ shower & oversized tub combobrWorkspace w/ desk & swivel chairbrFamily room w/ sleeper sofa, 55 4K smart tv & tv stand w/ fireplace insertbrBedroom 3 w/ king bed, dresser, loveseat & walk-in closetbrbrBackyard/pool area—brPatio furniture w/ gas fire pitbrBBQ gas grillbr4 Resin lounge chairs brBench w/ umbrellabrbrHigh-speed fiber optic internet provided for working, gaming, or streaming your favorite movies/shows.brbr**Pool is open May 15th-October 1st (or later if the weather permits)brbrCentrally-located in the charming Dogwood-Azalea neighborhood, one block from Frederica St.
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Exceptional(3)

$132.7

/ Nightly
Apartment

Private 2 bdrm apartment in the heart of the city. Pet friendly.

Owensboro, Kentucky, United States

Built in 1916 in the heart of the city, this private 2 bedroom apartment has easy access to all the main arteries in town and less than .5 miles all amenities you may want. Two bedrooms, one full bathroom apartment with fully stocked kitchen, washer and dryer.brThis is a house converted to two apartments, this listing 2 bedroom on the back side, and a 1 bedroom on the front side. The units are connected by a locked door. Contact me to rent both sides pending availability.
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Exceptional(42)

$182.34

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Private Vacation Home

The Bluegrass House

Owensboro, Kentucky, United States

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).brbrThis quaint space boasts a celebration of rich southern culture decor, and a cozy fireplace. br Soothe yourself in the year-round hot tub, private fenced-in backyard , soft wicker chairs on the deck, and spacious firepit to celebrate friendships and family. Cuddle with your mate on the long swing and tuck a little one in on the baby swing.brbrHouse is located in a neighborhood that is right off Frederica Street which is the main street of Owensboro and very close to several restaurants and other activities.brbrPlease review the house rules regarding pets if you plan on booking the property and bringing a pet.brbrIn addition, please keep eye on children around the hot tub area located on the back year during your stay.brWe accept pets by request only. Please note that the pet fee is not part of the booking fee. Any additional pet fee will be requested immediately after booking and after the request is approved. Dogs are only allowed regarding pets. No dogs over 50 lbs. each and limit two. Pricing is as follows.brbr1 dog under 50 lbs. 2 to 3 nights. $ 35.00 Two Dogs it is $70.00brbr1 dog under 50 lbs. 4 to 7 nights $ 70.00 Two Dogs it is $140.00brbr1 dog under 50 lbs. 7 to 30 nights $ 200.00 Two Dogs it is $250.00brbrWe reserve the right to cancel a booking if guests to not adhere to the additional pet fee and rules. brbrWhen you leave the house, your pet must be brought with you if going out for long periods of time (more than 2 hours) and should be in a crate if out for short periods. (Even the most well-behaved dogs will act differently when left in a strange environment. Dogs left alone, even crated, may bark and disturb other neighbors.brbrPlease ensure that your pet is on leash while out and around the house. brbrPlease be sure to pick up and dispose of any poop. brbrPlease do NOT walk the dog in the neighbor`s yard.brbrPlease eat and drink main course meals in the kitchen area and keep pets off of furniture.brbrReport any damages immediately.brbrThank you!
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Exceptional(1)

$365.21

/ Nightly
Private Vacation Home

Cozy Stylish 2 BR Home w/ Pool / Relax & Enjoy

Owensboro, Kentucky, United States

Whether you're here for a relaxing getaway, a fun trip with family and friends, or a business stay, this home offers the perfect blend of comfort and convenience. Step outside to enjoy a private backyard with a refreshing pool—perfect for sunny days or unwinding after a long day. Spacious, cozy, and inviting, it’s a place where you can truly relax and feel at home from the moment you arrive.
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Exceptional(31)

$120.01

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Private Vacation Home

The Cabin In Town - With A Rustic Flare

Owensboro, Kentucky, United States

The Cabin in Town is recently remodeled home from the 1950s with hardwood floors and original trim work.brbrThe house is centrally located in town on a nice quiet street and ready to receive guests.brbrIt accommodates five, with three bedrooms and one bath.brbrAmenities are included, and the house is fully furnished.brbrThe home is ready for guests - for either a short or longer stay. Let us know how we can be of assistance!
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Exceptional(38)

$137.92

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Private Vacation Home

Bluegrass Bungalow 2 bedrooms with large porch

Owensboro, Kentucky, United States

This 2-bedroom bungalow is perfect for your escape to Owensboro. With 1 queen bed and 2 twin beds, guests can enjoy a cozy stay in this cool retreat. AC, WiFi, and heating are available for your convenience. Book now and enjoy everything this bungalow has to offer.
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Exceptional(2)

$245.03

/ Nightly
Private Vacation Home

Black remodeled farmhouse minutes to downtown Owensboro

Owensboro, Kentucky, United States

Welcome to our completely remodeled 50's farmhouse located minutes from highway 54, downtown, and Owensboro Health Hospital. You are minutes from restaurants, bars, shopping, and entertainment. Enjoy the country feel right on the edge of town. 9 minutes to downtown.brbrThe home is family-friendly and boasts lots of indoor and outdoor space.brbrEnjoy the scenic rolling hills and country feel from the yard, while still enjoying the convenience of the short commute to all that Owensboro has to offer.brThe spacebrThe home features 3 bedrooms, 2 baths, and is family friendly. We provide toys and games to make all members of the family comfortable.brbrThe home also has good wifi those who work remotely.brbrThe home sits on 2 acres with room to enjoy the outdoors minutes away from shopping, restaurants, entertainment.brbr• Once or twice a week we must visit the property to maintain the grass in the yard. We will try our best to provide you with advanced notice and will be in and out as quickly as possible.
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Exceptional(25)

$131.39

/ Nightly
Private Vacation Home

The Green Garden Cottage is +1200 square feet house, centrally located

Owensboro, Kentucky, United States

The Cottage House is centrally located close to library, various amenities and 1 1/2 miles from Riverfront activities. This 1930s built home has all manner of charm including hardwood floors, glass door knobs, tall ceilings and rounded entry ways. The kitchen has been recently remodeled with new appliances, cabinets and countertops. The upstairs bedroom is a large finished attic with its own heating and cooling system. We do welcome pets, but please ask about our pet policy before booking.
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Exceptional(17)

$298.41

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Private Vacation Home

315 West 14th Street

Owensboro, Kentucky, United States

Newly redone 3 bedroom 2.5 bath home in the heart of Owensboro. Easy access to downtown and shopping. Amazing area to stroll the sidewalks and enjoy one of the best neighborhoods in town. A perfect home base if your visiting or having family over.
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Exceptional(23)

$184.73

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Private Vacation Home

1 King Bed + 1 Queen Bed + 2 Full Bathrooms Kitchen + Laundry Room + Patio

Owensboro, Kentucky, United States

Welcome to your home away from home at The Village Cottage! While you’ll feel tucked away in a peaceful, family-friendly neighborhood, this cozy 2-bed, 2-bath home offers the perfect retreat for anyone visiting Owensboro. Within just a few minutes, you can reach the convention centre, downtown, hospital, grocery stores, cafes, restaurants, movie theatre and the green belt. Whether your in town visiting family & friends or on a business trip, we look forward to hosting you!
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$320.2

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Spacious Private 3BR / 2BA Home — Sleeps 8 Comfortably

Owensboro, Kentucky, United States

This 3-bedroom house is perfect for your escape to Owensboro. Inside, guests find two queen beds and a cozy bunk bed, ideal for families or groups. The home features two bathrooms, each with a refreshing shower and convenient hair dryer. Enjoy a beautiful, serene space where comfort meets simplicity. Whether you’re relaxing indoors or exploring nearby, this tremendous house offers a welcoming retreat. We look forward to hosting you at our place.brFully furnished 3BR/2BA home in the center of Owensboro, close to hospitals, medical facilities, shopping, restaurants, entertainment, and sports complexes. Ideal for travel nurses, medical professionals, business travelers, and families seeking a comfortable mid-term stay. Unique and stylish space with high-speed Wi-Fi, smart TVs, blackout curtains, and everything needed for a true home away from home. Convenient 40 min to Holiday World .Great Walkable neighborhood close to workout facilities.
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$264.74

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Private Vacation Home

Spacious 5-bedroom house in charming Owensboro with AC, WiFi

Owensboro, Kentucky, United States

Escape to a delightful 5-bedroom house in Owensboro. This charming property features 2 queen beds, 1 king bed, 2 twin beds, and 1 futon, perfect for families or groups. With 3 bathrooms offering a bathtub, shower, and hair dryer, guests will feel right at home. Additional spaces include a living room with a library, television and sofa and a large family room with a sofa, (suitable for sleeping), withbrGames for adults and children. There is an enclosed screened in patio area at the back of the house. Enjoy your time in Owensboro at our fabulous house.l
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Home Most popular vacation rentals in Owensboro

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$517.70

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Spacious Home with Heated Swimming Pool + Hot Tub + Event Room + SLEEPS 23

Owensboro, Kentucky, United States

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$94.49

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Cozy, Furnished Corporate Rental

Owensboro, Kentucky, United States

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$132.70

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Private 2 bdrm apartment in the heart of the city. Pet friendly.

Owensboro, Kentucky, United States

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$160.90

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Private vacation home

Cozy Cottage home

Owensboro, Kentucky, United States

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Sleep 6

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$184.73

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1 King Bed + 1 Queen Bed + 2 Full Bathrooms Kitchen + Laundry Room + Patio

Owensboro, Kentucky, United States

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Sleep 4

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$193.24

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Centrally Located Mid Century Traditional Home

Owensboro, Kentucky, United States

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$199.93

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Center of city private Town Home W/fire pit &BBQ

Owensboro, Kentucky, United States

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Sleep 4

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$212.77

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Private vacation home

The Haven on Hill Ave

Owensboro, Kentucky, United States

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$365.21

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Cozy Stylish 2 BR Home w/ Pool / Relax & Enjoy

Owensboro, Kentucky, United States

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$298.41

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315 West 14th Street

Owensboro, Kentucky, United States

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Most Popular Cities in Kentucky