Vacation rentals in Owensboro

A clean, modern bathroom sink area features a white vanity with two spacious storage cabinets beneath. The sink is set against a light gray wall, with soap dispensers positioned on the countertop. A neutral-toned mat is placed in front of the bathtub.

4.85 out of 5 average rating, 226 reviews

Emma B's Place Close to Town and the Riverfront

Emma B's Place is newly renovated and ready for guests! Here you'll find a cozy atmosphere, comfortable beds, fully equipped kitchen, and brand new washer & dryer. The location is convenient to an award winning Riverwalk, shopping, great dining, and our central location offers a short commute to the entire city. If you prefer to stay in and relax, a 42-inch smart tv and wireless high-speed internet are available for your enjoyment. Lockbox self-entry. Your hosts live nearby if you need anything!

4.96 out of 5 average rating, 141 reviews

Home in Newburgh

The Cottage on W Main

Family friendly 2 bed 2 bath! Charming and convenient space in downtown historic Newburgh. Easy walk to the scenic riverfront and downtown area which includes ice cream shops, restaurants, shopping and hair salon. Short walk to beautiful Rivertown Trail! Come explore downtown Newburgh and with easy access to multiple sites in Evansville the location is fantastic! So many family amenities with no stairs inside house, stroller, pack-n-play, outlet covers, kids books, and highchair provided!

4.95 out of 5 average rating, 140 reviews

A fire pit area surrounded by six blue Adirondack chairs is set on a grassy lawn. Tall trees provide shade, enhancing the peaceful outdoor setting that invites gatherings and relaxation.

Home in Santa Claus

Christmas Cottage

One block away from Holiday World! This house is a close walk to the park and a 5m drive to Lincoln Boyhood National Park and many other attractions. The house has been lovingly prepared for a Christmas theme and is ready for guests with comfy bedding, updated kitchen and bathroom, large indoor and outdoor gathering area, and all sparkling clean. This house converts from an 8 person (upstairs only) to a 12-14 person (add 4 beds, bathroom, additional kitchenette, and washer and dryer).

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.

4.88 out of 5 average rating, 242 reviews

A charming cottage is framed by a snow-covered landscape. The light green exterior is complemented by dark blue front door and window shutters. Surrounding shrubbery is neatly trimmed, and a pair of lampposts stands at the entrance, enhancing the inviting facade.

Bungalow in Owensboro

The Green Garden Cottage

The Cottage House is centrally located to library and 1 1/2 miles from Riverfront. This 1930s home has hardwood floors, glass door knobs, and rounded entry ways. The kitchen has been remodeled with new appliances, cabinets and countertops. The upstairs bedroom is a large finished attic with its own heating and cooling system. We do allow pets for an additional one-time fee of $45 paid through Airbnb. No more than two dogs and we ask that animals not sleep or be on the beds.

4.94 out of 5 average rating, 31 reviews

A serene landscape showcases a calm lake surrounded by dense greenery and mature trees. The water reflects the blue sky and puffy clouds, creating a tranquil setting. Grass-covered grounds lead gently to the water's edge, offering a peaceful environment for relaxation.

Townhouse in Newburgh

Quiet home on the water downstairs duplex A

Gorgeous setting with incredible water views from this lower level one bedroom/one bath duplex unit with full bed and queen Murphy bed as well as equipped kitchen. Country living that feels like a resort with a shared deck and gazebo, water access, fire pit, fishing, hiking and wild life. Unit includes private entrance, refrigerator, range/oven, microwave, flatscreen tv, WiFi, coffee maker, dishes/utensils, pots/pans. Pets: require non-refundable pet deposit of $250.

A sheltered pavilion with a green metal roof is positioned along the waterfront. Stone columns support the structure, and views of the Ohio River can be seen in the background. Surrounding trees provide shade, enhancing the peaceful outdoor setting.

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.

Vacation home in Owensboro

A vibrant dining table is set with a large green plate containing rice, beans, and a filled tortilla, topped with a drizzle of sauce. Glasses of beverages, chips in a basket, and various sauces accompany the meal, creating an inviting atmosphere.

4.93 out of 5 average rating, 126 reviews

The little big cozy house

The little big cozy house offers you a place where you can relax and feel at home. a spacious kitchen with all the necessary elements such as The 3 bedrooms ,that invite you to rest with very suitable beds For you to spend a magnificent and comfortable night. The patio is a space where you can enjoy a grill surrounded by family or friends. This house is an excellent location that gives you quick access to any part of owensboro.

4.92 out of 5 average rating, 26 reviews

A shaded outdoor patio area features a sectional sofa with patterned cushions, a coffee table, and an outdoor dining space. The brick exterior and large windows provide a view of the surrounding greenery. A grill is positioned nearby for barbecues.

Home in Madisonville

Great space, no cleaning fees, City park view.

Forget your worries in this spacious and serene space. A home away from home. 3 bedrooms, each with Tv. Spacious kitchen and living room. Washer and dryer in basement. Beautiful view of lake and wildlife. Basement gives added space to stretch out. Ping pong, Ms. Pac-man, foosball, corn hole and kids toys. Advance notice for use of hammock, bicycles or kayak. Need more space, second home available next door for booking.

A charming cottage exterior features a light gray façade with white trim and a bold pink front door. Flanking the entrance, white rocking chairs are positioned on the porch. Lush greenery and blooming blue hydrangeas enhance the inviting front yard, with a stone wall and steps leading to the entrance.

4.94 out of 5 average rating, 143 reviews

Cottage by the River & Convention Center

Great little cottage located in the bustling newly renovated Riverfront. 3 Blocks from Convention Center & very near Bluegrass Music Hall of Fame & Museum, RiverPark Center Performing Arts, Owensboro Historical Museum, Owensboro Art Museum, Smother's Park, restaurants, shopping, churches & the Antique Mall. All in walking distance or get on the free trolley 2 blocks over. Free WIFI, Smart TVs, Free Street Parking.

4.87 out of 5 average rating, 129 reviews

A grassy backyard overlooks a river, framed by tall trees providing shade. A circular fire pit with stones is positioned centrally in the yard, inviting gatherings. The tranquil water reflects the greenery, enhancing the connection to nature.

Cabin in Falls of Rough

Waterfront Cabin with Hot Tub

Relax with the whole family in this adorable riverfront cabin. Gather around a campfire, cookout, fish, kayak, or go for a dip in the hot tub all from the backyard. And if that's not enough, take a stroll around the resort and immerse yourself in the beautiful scenery, historic falls and Green Farm, golf course clubhouse, and more! Oh and don't forget Rough River Lake and the State Park are just minutes away!

4.97 out of 5 average rating, 340 reviews

A wooden cottage entrance is framed by two large windows, adorned with potted plants. A comfortable seating area is visible adjacent to the entrance, along with a small dining table and chairs on the deck, inviting outdoor relaxation.

Cottage in Newburgh

Boho Burgh Cottage with full kitchen/clawfoot tub

The Original Cozy Cottage is located in the heart of downtown Newburgh, this wonderfully decorated cottage offers a full kitchen, claw foot tub, walk in closet, deck, and partial river views. Shops and restaurants within steps and only 15 minutes from downtown Evansville. *Please read all info before booking*

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Hotels

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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

4.95 out of 5 average rating, 306 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

A spacious living area features a large wooden dining table surrounded by several chairs. A comfortable couch and rocking chair provide additional seating. A flat-screen television is mounted on a brick wall, with windows dressed in light curtains allowing natural light to brighten the room.

4.93 out of 5 average rating, 116 reviews

This_is_HORSE_Country

5 out of 5 average rating, 8 reviews

A wooden deck overlooks a serene lake, equipped with a lightweight chair and a small grill. Surrounding greenery is reflected in the water, creating a calm environment. Sunlight filters through the trees, highlighting the natural beauty of the setting.

Cabin in Drakesboro

Private fishing retreat

4.98 out of 5 average rating, 47 reviews

Peaceful Stay | Relax & Unwind

4.88 out of 5 average rating, 105 reviews

A spacious living area features a sleek fireplace with decorative accents, complemented by a ceiling fan. A flat-screen TV is mounted above the mantel, and artwork adorns the walls. Light wood flooring contributes to the inviting ambiance, with comfortable seating arranged for relaxation.

Apartment in Owensboro

My Old Kentucky Home: Downtown Stylish 1 Bedroom

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, 244 reviews

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

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

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Vacation rentals with jacuzzis in Owensboro

A charming exterior of a gray house is framed by neatly trimmed hedges and a manicured lawn. A short concrete path leads to the front door, which features decorative details. A small orange awning adds a pop of color above the front window, set against a bright blue sky.

4.96 out of 5 average rating, 45 reviews

Hill Ave home

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, 90 reviews

The Bluegrass House

4.96 out of 5 average rating, 283 reviews

A serene lakeside view captures a quaint cabin reflected in calm waters. Lush green grass surrounds the water's edge, while trees frame the background under a blue sky dotted with clouds.

Cabin in Dixon

Crouse’s North Ninety Lake House

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

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

5 out of 5 average rating, 72 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

4.97 out of 5 average rating, 68 reviews

An inviting entrance features a small round table and two chairs under a red umbrella, surrounded by vibrant rose bushes and green landscaping. The front door is adorned with a decorative wreath, providing a warm welcome to guests.

Home in New Harmony

Quaint, Quiet & Cozy Cottage in New Harmony

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

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Other great vacation rentals in Owensboro

4.94 out of 5 average rating, 50 reviews

A cozy place that helps you feel right at home.

4.71 out of 5 average rating, 14 reviews

A covered porch area is featured, equipped with two green chairs and a table. Soft lighting is provided by string lights overhead. Enclosed by a black privacy barrier, the space offers views of the surrounding greenery and distant structures.

Home in Sacramento

CROSSROADS COTTAGE

4.99 out of 5 average rating, 74 reviews

A charming single-story home is depicted with a light pink exterior and a sloped gray roof. A paved driveway leads to a two-car garage, flanked by well-maintained shrubs and small trees. Blue skies and greenery enhance the welcoming appeal of the property.

Home in Beaver Dam

Rise and Shine on Main

4.88 out of 5 average rating, 25 reviews

A living area is highlighted by a modern television mounted on a low white console, complemented by blue LED lighting. A faux fireplace sits beneath the TV, and a comfortable blue armchair adds a pop of color. A small table and decorative wall art complete the space.

Home in Evansville

City Cottage

4.98 out of 5 average rating, 58 reviews

A cozy fire pit area is set in an open green space, featuring two red Adirondack chairs arranged around a central fire pit. The surrounding landscape includes expansive fields and distant trees, creating a serene outdoor atmosphere.

Home in Madisonville

Whippoorwill Farmhouse

4.97 out of 5 average rating, 34 reviews

A spacious wooden deck is illuminated by warm string lights, creating a welcoming atmosphere. Dining chairs are arranged around a modest table, with a grill and potted plants nearby. The backdrop features a cozy log cabin, enhancing the outdoor experience.

Cabin in Henderson

Lakeside Log Cabin: Venue • Hunting • Fishing

4.97 out of 5 average rating, 128 reviews

Soft yellow string lights are displayed overhead in the outdoor space, illuminating a stone pathway and lush green grass. A wooden deck is visible in the foreground under evening sky, creating a relaxed atmosphere for outdoor activities.

Home in Newburgh

Little Monticello