Vacation rentals in Owensboro

4.98 out of 5 average rating, 137 reviews

Cottage in Owensboro

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.

An open-concept living area is highlighted by modern furnishings and natural light. A sectional sofa is paired with a circular coffee table, while a well-equipped kitchen with bar seating is visible in the background. Stylish artwork complements the neutral color palette.

4.94 out of 5 average rating, 110 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.

4.96 out of 5 average rating, 284 reviews

A charming cabin is reflected on the calm surface of a pond, surrounded by lush greenery and trees. Fluffy clouds are visible in the blue sky above, complementing the peaceful rural setting. A small boat is moored nearby, adding to the serene atmosphere.

Cabin in Dixon

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.

4.97 out of 5 average rating, 165 reviews

The cottage features a welcoming front porch adorned with red shutters and a bright red door. Two large, round rocking chairs are positioned on the porch, surrounded by greenery and a blue planter. The pathway leads to the spacious entrance.

Cottage in Maceo

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 ONLY ONE bedroom which can be made into EITHER two California twins OR one California king -Wifi ..Smart TV... use your Netflix and so on with this TV ...... Kitchen has everything you need ..Eating/work space. Comfortable recliner chairs ... Use of pool/ plenty of places to roam on farm .

4.88 out of 5 average rating, 105 reviews

The entrance features a welcoming hallway with warm wooden flooring and soft grey walls. A simplistic table stands against the wall, adorned with decorative items. Light is provided by an intricate chandelier, creating an inviting atmosphere. Two doors are visible, leading to additional spaces.

Apartment in Owensboro

My Old Kentucky Home: Downtown Stylish 1 Bedroom

A few minute walk to Downtown Owensboro! Welcome to our charming Airbnb 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! Book now for an exceptional stay!

4.95 out of 5 average rating, 131 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 kitchen space is presented, featuring dark cabinetry and a speckled granite countertop. A coffee maker sits prominently on the counter beside decorative items. Natural light enters through a nearby door, highlighting the organized shelves with baskets and a welcome sign.

5 out of 5 average rating, 145 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.

4.97 out of 5 average rating, 379 reviews

Lush trees with vibrant green and yellow leaves create a canopy in a tranquil forest. Sunlight filters through the branches, illuminating the forest floor covered in fallen leaves. The scene conveys a serene natural environment, ideal for exploration and relaxation.

Cottage in Owensboro

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.

A screened-in patio features a curved wicker seating arrangement with plush cushions. A minimalistic lamp stands beside the seating, while a fan is mounted on the ceiling. A framed artwork is displayed on the wall, offering a subtle decorative touch.

4.97 out of 5 average rating, 159 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.

4.98 out of 5 average rating, 271 reviews

A two-story building features a spacious deck with a railing, overlooking the river. A staircase leads to the upper entrance, while a small seating area with colorful chairs is visible by the shoreline. The sky displays soft pink and orange hues at sunset.

Loft in Newburgh

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.

A hallway featuring a light-toned rug runs alongside white cabinetry and multiple doors. A farmhouse-style sliding door is positioned at the end of the hall, contributing to the modern design. Natural light is provided by a stylish ceiling fixture.

4.95 out of 5 average rating, 217 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.

4.98 out of 5 average rating, 137 reviews

Bungalow in Owensboro

Bluegrass Bungalow: Historic Charm, Modern Comfort

Welcome to the Bluegrass Bungalow, a charming 1924 two-bedroom, one-bath home that seamlessly blends historic charm with modern amenities. Located near the Ohio River and downtown, this cozy retreat is just moments from top restaurants and shopping. Enjoy the preserved vintage details alongside a fully renovated kitchen and bath, including a spacious walk-in shower.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Popular amenities for Owensboro vacation rentals

Self check-in

Pet friendly

Hot tub

Laptop-friendly workspace

Gym

Stay near Owensboro's top sights

Moonlite Bar-B-Q Inn18 locals recommend

Bluegrass Music Hall of Fame & Museum32 locals recommend

Spirits at The Miller House23 locals recommend

O.Z. Tyler Distillery18 locals recommend

The Famous Bistro18 locals recommend

Old Hickory Bar-B-Que11 locals recommend

Dog friendly vacation rentals in Owensboro

A bright living room is featured with a comfortable sofa and decorative throw pillows. A television is situated on a spacious console against a light-colored wall. Natural light enters through a front window, complemented by sheer blue curtains. The ceiling fan adds to the cozy ambiance.

4.98 out of 5 average rating, 47 reviews

Peaceful Stay | Relax & Unwind

Guest suite in Evansville

A guest suite is displayed with a comfortable queen bed adorned with a patchwork quilt. A small kitchenette is visible, featuring a mini fridge and microwave. A bathroom is partially shown, revealing a sink and toilet. Warm green walls create a cozy ambiance.

4.81 out of 5 average rating, 245 reviews

Private Suite/Sleeps 3/Center Town/Pets OK!

4.94 out of 5 average rating, 80 reviews

A well-kept outdoor space is shown, featuring a black swing and a gas grill surrounded by lush greenery. Stone pathways and beds of colorful plants add interest, while a blue umbrella provides shade. The area suggests a peaceful setting for relaxation.

Home in Huntingburg

Spacious 1450 sf 2 BR Private Suite Apartment

4.94 out of 5 average rating, 31 reviews

A charming duplex unit is shown from the exterior, featuring a light grey facade and an inviting front porch. Surrounding gardens include well-maintained landscaping with flowers and greenery. A garage is visible on the left side, and a shared deck and gazebo are seen in the background.

Townhouse in Newburgh

Quiet home on the water downstairs duplex A

4.96 out of 5 average rating, 141 reviews

A charming one-story house with a light yellow exterior is highlighted by white trim and a gabled roof. The front porch, supported by two columns, features a brick pathway leading to the door. Black shutters flank the windows, set against a backdrop of lush greenery.

Home in Newburgh

The Cottage on W Main

4.88 out of 5 average rating, 252 reviews

Two adjacent bedrooms are visible through an open door. One room features a king-sized bed dressed in a white quilt, with elegant drapery framing a bright window. The other room displays a cozy bed with layered bedding and a soft pink accent, along with tasteful decorative furnishings.

Apartment in Evansville

Semper Fulgens: Historic Riverfront Home

5 out of 5 average rating, 8 reviews

A grassy area is bordered by tall trees, providing a natural backdrop. Stacked logs are present in the distance, offering a rustic element. The space is open and offers a peaceful, private environment, suited for tents or vehicles.

Campsite in Evansville

Park RV, Tent or Camper While Traveling

Cottage in Falls of Rough

A covered patio area features a wooden ceiling with visible wooden beams and ceiling fan. Seating arrangements consist of wicker chairs positioned around a table, complemented by potted ferns. Natural greenery surrounds the space, enhancing the serene outdoor setting.

4.91 out of 5 average rating, 103 reviews

Cooter Valley on The Rough

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Vacation rentals with jacuzzis in Owensboro

4.92 out of 5 average rating, 239 reviews

The wooden cabin features a traditional design with a peaked roof and a red door. Surrounded by trees and under a clear sky, it is situated near the Ohio River, with gravel pathways leading to the entrance and an expansive view of the water visible in the background.

Cabin in Cannelton

Isaak's Hideaway - "Newly Remodeled"

4.87 out of 5 average rating, 131 reviews

A peaceful covered porch is visible, featuring two red rocking chairs. Lush green grass extends from the porch to the riverbank, where a calm river flows, and a fire pit is located nearby. Trees provide shade and enhance the serene outdoor setting.

Cabin in Falls of Rough

Waterfront Cabin with Hot Tub

4.97 out of 5 average rating, 125 reviews

The log cabin is set on a hillside surrounded by trees, featuring a red metal roof and large windows. A wooden deck leads to the entry, providing views of the Ohio River and nearby farmland. The natural setting contributes to a peaceful ambiance.

Cabin in Leavenworth

BIG TIMBER RIVER CABINS, "The Hawk's Nest"

4.94 out of 5 average rating, 278 reviews

A rustic log cabin with a two-story design is surrounded by lush greenery. The spacious front porch features wooden decking, outdoor furniture, and a hot tub, inviting relaxation. Large windows allow natural light to brighten the cabin's interior, offering views of the idyllic landscape.

Cabin in Derby

Derby Serenity

5 out of 5 average rating, 34 reviews

A relaxing hot tub is illuminated with blue lighting, offering a view of the lake at sunset. Two glasses of wine and a bottle are positioned on the edge, enhancing the serene atmosphere created by the warm water and colorful sky.

Home in Falls of Rough

On The Rocks

4.91 out of 5 average rating, 89 reviews

A spacious living room features a large sectional sofa and an armchair, complemented by a decorative area rug. Natural light enters through light-filtering curtains, while a round coffee table sits at the center. A barrel accent adds a rustic touch.

Home in Evansville

Farm House on Oakhill

4.91 out of 5 average rating, 23 reviews

A relaxing hot tub is situated on a wooden deck, surrounded by a gazebo draped with soft curtains. The outdoor area features a grassy lawn and a brick home nearby, with trees in the background reflecting seasonal changes.

Home in Newburgh

Modern Ranch 3 BDRM, sleeps 6 + HOT TUB

Vacation home in Evansville

An indoor pool area features a long, narrow pool, surrounded by large windows that allow natural light to fill the space. The tiled floor is complemented by potted plants, and wicker chairs with cushions are arranged nearby for seating.

4.96 out of 5 average rating, 161 reviews

Nugent House

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Other great vacation rentals in Owensboro

4.94 out of 5 average rating, 34 reviews

The bathroom features a spacious layout with wooden cabinetry and a large mirror above the dual sinks. A corner bathtub is highlighted, and light-colored flooring enhances the overall atmosphere. A door leads to a private area, contributing to the functionality of the space.

Home in Dale

X Marks the Spot(Blue)1.5 miles from Holiday World

4.94 out of 5 average rating, 50 reviews

A cozy place that helps you feel right at home.

4.88 out of 5 average rating, 25 reviews

Home in Evansville

City Cottage

4.98 out of 5 average rating, 64 reviews

A vintage cabin stands surrounded by lush greenery, while warm lights glow from its windows as dusk approaches. The cabin's log exterior is showcased against a colorful sunset, and a gravel path leads towards the entrance, creating a welcoming feeling in the serene setting.

Cabin in Madisonville

My Old Kentucky Home Log Cabin Private Retreat

5 out of 5 average rating, 14 reviews

Green River Getaway

4.87 out of 5 average rating, 46 reviews

A screened-in porch features comfortable seating with vibrant turquoise cushions and coordinating pillows. A coffee table sits at the center, surrounded by wicker furniture. Sheer white curtains frame the windows, allowing natural light to fill the space and provide a connection to the outdoors.

Cottage in Westview

Serene Lakefront Cottage Home, relax and enjoy!

5 out of 5 average rating, 12 reviews

A covered patio with wooden beams provides a shaded area for outdoor relaxation. A seating arrangement is positioned around a central fire pit, surrounded by potted plants and greenery. A neatly maintained lawn extends around the patio, contributing to an inviting outdoor space.

Home in Evansville

Huge Home for Everyone!