Vacation Rentals By Owner In Owensboro, KY

This 3bd 1ba is located ten minutes from downtown, five minutes from restaurants and shopping, and five minutes from the airport. Recently remodeled. Fully furnished with all the necessities. Patio and outdoor grill, firepit. Perfect for work stays or visiting family in the area.

Remodeled 3bd house near airport.

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

Exceptional(5)

Select Dates for Price

step back in time while still having some modern amenities. This charming downtown home built in 1891 will take you back to Victorian design with 10' Ceilings original hardwoods and built in cabinetry.

Historic Downtown Home with Mid Century Flair

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

Exceptional(1)

$221.71

Our Village gate is cozy and quaint yet strategically positioned in close proximity to community amenities, restaurants,shopping,and downtown area . A short distance to hop on the Greenbelt to enjoy a walk with your family .Also about 30 miles to Holiday World! Have fun with the whole family at this stylish place!Make yourself at home in this 3-bedroom Owensboro retreat. This pleasant house features 1 king bed, 1 queen bed, and 1 bunk bed, perfect for families or friends traveling together. We think our place will help you experience everything Owensboro has to offer.

Charming 3-bedroom house with king bed , pet friendly

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

Exceptional(13)

$424.98

Just blocks from the Riverfront, this 1896 Victorian beauty has stood the test of time. Enjoy the best of both worlds with authentic, rich architecture offering just a hint of modern flare. This 4 Bedroom, 3 Bath home is suited for up to 12 guests and feels like your home away from home. Pamper yourself with a weekend getaway or make your lifelong dreams come true. Enjoy the peaceful backyard and soak up the history of Old Owensboro just the way you'll always remember it.

Downtown Dream in Owensboro Ky

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

Exceptional(14)

$328.2

The City House is a renovated 4 bed / 2.5 bath home in the heart of Owensboro. The convenient location makes it easy to get to restaurants, shopping, parks, downtown or sporting events. In less than 10 minutes, you can enjoy just about everything Owensboro has to offer whether it’s barbecue, bourbon or Bluegrass!

Newly renovated- 2.5 mi to Downtown Riverfront

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

Exceptional(75)

$341.11

This 3 bed, 2 bath relaxing retreat to the country has unparalleled views of 100s of acres of farmland. It is a home that is full of light and country farmhouse charm. Located just a short 15 minute drive from town, you are only 5 minutes from entertainment such as antique shopping, alocal bar & grill, fishing. Cecil Farms Produce Farmstand and Greenhouse is just up the road to shop fresh vegetables, gifts, flowers and enjoy seasonal experiences. Outdoors is private, without direct neighbors, atop a hill. br

The Robinette House: Endless view of rolling farmland

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

Select Dates for Price

Apartment

My Old Kentucky Home: Downtown Spacious 3 Bedroom

Owensboro, Kentucky, United States

A few minute walk to Downtown Owensboro! Welcome to our charming apartment in Owensboro, KY! Experience modern comfort and historic charm in the heart of the city. Relax in the cozy living area, cook in the fully equipped kitchen, and enjoy a peaceful night's sleep in the comfortable bedroom. Explore nearby attractions, indulge in local cuisine, and make unforgettable memories. Only a few blocks from Smothers Park, Bluegrass Museum, and more!brbrBook now for an exceptional stay!brThe spacebrOur apartment in downtown Owensboro, KY offers a delightful space where you can unwind and feel at home. The living area is designed for relaxation, with comfortable seating and a warm ambiance. Stay connected with high-speed Wi-Fi or enjoy your favorite shows on the smart TV.brbrOur apartment's location is unbeatable, placing you in the heart of Owensboro. Immerse yourself in the city's rich history, visit nearby Smother's Park, or take a leisurely stroll along the riverfront. Indulge in the famous local barbecue and experience the warm Southern hospitality of the area.brbrWhether you're here for a weekend getaway, a family vacation, or a business trip, our apartment provides the ideal home base. We take pride in offering exceptional hospitality and ensuring your stay is comfortable and memorable.brbrBook now and discover the best of Owensboro, KY at our charming Airbnb. With the hospital nearby and a variety of excellent restaurants within walking distance, convenience and delightful experiences await. We can't wait to welcome you and help create unforgettable memories!brbrOther things to notebrbr13-minute walk to the Owensboro Convention Centerbr9-minute walk to the Bluegrass Museumbr11-minute walk to the RiverPark Centerbrbr9-minute drive to Owensboro Health

Bed

Bath

Sleeps

$197.58

Easily access all the Big O has to offer from this centrally located, nonsmoking home nestled in the beautiful Dogwood Azalea Area. Wake up & get going with a 5 minute stroll to Starbucks or let your nose guide you to the famous Old Hickory restaurant for some tasty bbq. Enjoy a short bike ride to Owensboro’s happening downtown (2 bikes included) or trek a nearby route to the Greenbelt. Your home includes 2 big screen Smart TVs, Free WiFi, exercise room, & lots more!

Clean & comfy 3 bdrm/2 bath home; perfect location

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

Select Dates for Price

This is a beautiful executive 2 bedroom house 5 mins from town with a private location. Its hundred percent non- refundable property. brbrIts is very calm with concrete drive and its on a acre and a half of land.

Elegant country living, Owensboro, KY

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

$483.94

Hot Tub On Hill /SHORT 40 MIN DRIVE TO HOLIDAY WORLD SPLASHIN ' SAFARI . A very spacious vacation spot the whole group will enjoy! Easy access to everything and centrally located. Close to downtown, the regional airport and all major attractions the city has to offer. Unbeatable location that puts you minutes away from boutique shopping, fine dining, concerts on the river, festivals ,nightlife and sport facilities. Pool , hot tub, Fire-Pit with outdoor patio and BBQ with enough seating for 14 , GREAT for multiple families with two separate living areas. Let the house on Hill Make your family gatherings memorable.

Hot tub/pool/firepit/ 3 bedroom Home center of town 2 Livingroom's sleeps 12

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

Exceptional(10)

$217.19

This uniquely remodeled Hill Ave. Home is the perfect home for your trip to Owensboro Now we have 3 person hot tub for your enjoyment at no extra charge! With 3 bedrooms, including 2 queen beds and 1 twin bed and a queen air bed in the den! With 1 full remodeled bath inside which has tub, shower with exhaust fan! This welcoming property offers tremendous comfort for guests. The soothing ambiance of the living room and den featuring an additional queen air bed, provides a cozy space to relax after a day of exploring. Enjoy the amenities such as central air, WiFi, washer/dryer, dishwasher, toaster, and nuwave air fryer! Dishes, pots and pans, and utensils provided! Nice deck, grill, and table. We have a tv in the living room and den with ceiling fans! For more fun we have a pingpong table and multigame table, checkers and chess, 2 decks of cards, cornhole or go across the street to the healthpark to swim, play basketball, use the walk track and use weight room or use sauna! The 1 bathroom, 1 with bath & shower to ensure that everyone can freshen up before heading out to enjoy the attractions and many tasty restaurants of Owensboro and enjoy our Hill Ave Home! The home is centrally located so you can quickly get to any part of town with grocery, gas station, hardware store and restaurants just a few blocks away! Everyone that has stayed in the Hill Ave. Home have loved it including one couple that just left this week got home and booked it again in 2 to 3 weeks! We now have a hot tub and a high chair to add to what we have to offer!

Uniquely remodeled 3 bdrm 1 bth home in safe area! Fenced in with a large deck!

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

Exceptional(9)

$228.13

Escape to comfort in our spotless, clutter-free home, where cozy meets clean! Enjoy pristine bathrooms, plush linens, and a relaxing, welcoming space that feels like your home away from home—perfect for family getaways or the business executive seeking a peaceful retreat.

Welcome to simple comfort a like new family friendly home Full of accommodation

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

Exceptional(4)

$244.36

Surrounded By 10 Wooded Acres | Furnished Lake-View Deck | Dogs Welcome w/ FeebrbrUnplug and unwind at this one-of-a-kind Owensboro vacation rental, where the charm of a log cabin meets the tranquility of a lakeside getaway. The 3-bedroom, 1-bath home promises a rejuvenating retreat with loved ones, whether you enjoy warm evenings beside the stone fireplace or lively afternoons lounging on the deck. Book today and get ready to discover the magic of this woodland gem!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 2 queen bedsbr- Bedroom 2: 1 bunk bed (twin/full)br- Bedroom 3 (Loft): 1 full bedbr- Additional Sleeping: 1 portable cribbrbrINDOOR LIVINGbr- Fireplace, flat-screen TVbr- Dining tablebr- Work deskbr- Wood-burning stove (decorative only)brbrOUTDOOR LIVINGbr- 2 decks, outdoor seatingbr- Patio, fire pit, charcoal grillbr- Lake viewsbr- 10-acre propertybrbrKITCHENbr- Refrigerator, stove/oven, microwavebr- Drip coffee maker, cooking basics, dishware & flatwarebr- Trash bags & paper towelsbrbrGENERALbr- Central heating & A/Cbr- Towels & linens, complimentary toiletries, hair dryerbr- Washer & dryerbr- Free WiFi, keyless entrybrbrFAQbr- 1 exterior security camera (facing out)br- Pet fee (paid pre-trip)brbrACCESSIBILITYbr- 2-story home, 3 steps to enterbrbrPARKINGbr- Driveway (5 vehicles)brbr-- THE LOCATION --brbr- 1 mile to Windy Hollow Campground: fishing, swimmingbr- 13 miles to Owensboro: entertainment, museums, restaurantsbr- 13 miles to Western Kentucky Botanical Gardenbr- 1 mile to Windy Hollow Speedwaybr- 84 miles to Mammoth Cave National Parkbr- 149 miles to Nashville International Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $75 fee (+ fees & taxes, dogs only, 2max)br- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 2-story home requires 3 steps to enterbr- The wood-burning stove is not available for guest usebr- Your safety matters. This property features 1 exterior security camera on the front door facing the front entry. The camera is outward facing and does not look into interior spaces. The camera records video and sound when activated by motion

Cabin

Lakefront Log Cabin in Kentucky: Fire Pit & Grill!

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

Exceptional(1)

$96.9

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!

Cozy, Furnished Corporate Rental

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

Exceptional(28)

$277.52

The Gathering Place is a 2285 sqft house with 5 bedrooms, 2 full bathrooms, large kitchen with dining space. The house was built in the 1950s, well maintained and recently remodeled. There are hardwood floors throughout the first level of the house and it is conveniently located in the center of town. The house has a finished upstairs, with two bedrooms, full bath and separate AC unit for comfort and a partially fenced backyard.

The Gathering Place

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

Exceptional(5)

$322.77

Welcome to the West Wing, that can sleep up to 14 guests! Perfect location, top-notch safety and hygienic measures, and a focus on ultimate comfort. Whether you're planning a family reunion, work trip, or on a solo adventure, our stunning property offers the perfect combination for an extraordinary experience.brbrLocated in a highly desirable location, beside Griffith Avenue and 1.2 miles from downtown. Our VRBO offers easy access to local events, restaurants, and shops. Whether you're seeking adventure, relaxation, or entertainment, our central location ensures that it's all within reach.brbrUpon entering, you'll be greeted by an expansive and beautifully decorated living area, designed with both comfort and style in mind. The open floor concept creates a seamless flow between the living, dining, and kitchen area.brbrThere are three generously sized bedrooms plus a bunk room, ensuring that everyone has their own personal retreat. Each room is furnished with comfortable beds and high-quality linens. Ensuring that you wake up feeling refreshed and rejuvenated.brbrThe bathrooms are equipped with modern fixtures, fresh towels, and toiletries that are provided for your convenience. One of the standout features located in the master bedroom is the hand rail and no-step shower, which provides easy access for guests with mobility concerns or those who prefer a step-free shower experience. Whether you require a wheelchair or simply appreciate the convenience, our no-step shower and handrail ensure that your bathing experience is comfortable and stress-free. .brbrThe fully equipped kitchen features high-end appliances, ample counter space, and all the necessary utensils and cookware. Whether you prefer a gourmet meal or a quick breakfast before heading out, this kitchen has everything you need. The open dining area offers a large table and seating for guests, creating a central hub for shared meals and lively conversations.brbrTo enhance your comfort, our VRBO provides high-speed Wi-Fi, ensuring that you can easily connect with loved ones or catch up on work. There are four large smart TV’s, allowing you to stream your favorite shows, sports, and movies. Other amenities include an on-site vending drink machine and a washer and dryer for your convenience.brbrOur VRBO also offers outdoor spaces for you to enjoy. As you step outside, you'll discover a spacious outdoor area, perfect for enjoying the beautiful surroundings. A private patio provides a setting for morning coffee or evening cocktails. These extras ensure that there's something for everyone, making your stay both enjoyable and memorable.brbrOur secure single car garage parking, ample driveway parking (3-4 vehicles), public street parking.brbrAs responsible hosts, we prioritize the safety and well-being of our guests. Our property is equipped with modern safety features, including secure locks, smoke detectors, fire extinguishers, first aid kit, ensuring your peace of mind throughout your stay. We maintain cleaning and sanitization protocols to maintain a pristine and hygienic space for our valued guests.brbrBook your stay with confidence, knowing that your comfort and well-being are our top priorities. We look forward welcoming you to your home away from home.

524 West 15th Street - SLEEPS UP TO 14

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

Exceptional(20)

$239.48

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.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.

Blue Moon Cottage: Music Room, Inground Pool

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

Exceptional(1)

$229.17

Welcome to Owensboro . Enjoy a stylish experience at this Touch of Grey Town Home nestled in the center of town . Stylish modern design and open living room concept is close to downtown regional airport and all major attractions the city has to offer. Unbeatable location that puts you minutes away from boutique shopping, fine dining, wine tasting , concerts on the river, festivals , nightlife and of coarse the Bluegrass Hall of Fame & Museum . Modern luxury design meets casual elegance.

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

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

$216.15

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

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

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

Most popular vacation rentals in Owensboro

$68.33

Remodeled 3bd house near airport.

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

$159.11

Agritourism

Charming 3 bedroom, 2 bath farmhouse just outside of Owensboro, KY

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

$148.87

Cottage

Comfy Cottage

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

$228.13

Welcome to simple comfort a like new family friendly home Full of accommodation

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

$148.81

Charming Midtown Manor 2 Bedroom + Bonus Room near Restaurants and Parks

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

$215.96

NEW LISTING! The Cabin | Tranquil Lakefront Retreat by RedAwning

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

$96.90

Cozy, Furnished Corporate Rental

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

$341.11

The Robinette House: Endless view of rolling farmland

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

$217.19

Uniquely remodeled 3 bdrm 1 bth home in safe area! Fenced in with a large deck!

Owensboro, Kentucky, United States

Bed

Bath

Sleeps

$171.75