Holiday rentals with outdoor seating in Owensboro

4.95 out of 5 average rating, 354 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

This House is located in a quiet neighborhood one block off Main street here in Beaver Dam, KY. Enjoy a nice cozy country home while you visit. It is fully finished so you will feel right home. The property sits on a corner lot with access from both streets. The house has a front porch for lazy evening to catch some fresh air. You can pull right up underneath the carport for easy access to the back door for entry. The home offers a nice yard and fire pit. You are minutes from stores/ food.

4.96 out of 5 average rating, 172 reviews

A sliding door opens onto a spacious deck, framed by a wrought iron screen. Outdoor seating is positioned on the deck, facing a green yard and trees, allowing for a serene view of nature.

Loft in Hartford

Cozy One Bedroom Apartment in the Country

What was originally a hay loft has been converted into a country chic barn apartment. We would love to host you and your friends and family (including actual kids and fur kids) on our property. Children love collecting eggs from the chicken coop and everyone loves a short hike to the creek. We are only an hour from Mammoth Cave National Park and an hour from Holiday World in Santa Claus Indiana. The local community has charming little shops, several restaurants, and The Beaver Dam amphitheater.

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.

4.92 out of 5 average rating, 120 reviews

The Bluegrass House

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).

5 out of 5 average rating, 100 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

The Storehouse, a church built in the 1890s, is nestled in the serene backdrop of Grandview, Indiana. This former sanctuary has been thoughtfully transformed into a 3 BR home, perfectly blending old-world charm with contemporary amenities. You will love the original hardwood floors and stained glass windows in every room. Less than 15 min. from Holiday World and Lincoln State Park, there is much to do. Return and unwind in the private hot tub or gather around the fire pit under the stars.

4.98 out of 5 average rating, 167 reviews

The exterior of a renovated two-story home is featured, showcasing a distinct architectural design with exposed beams. Large windows allow natural light to enter, while a welcoming front door is framed by decorative lighting fixtures. A concrete pathway leads to the entrance.

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.

A single-story home with a brick facade is presented. The driveway leads to a garage, while a well-maintained lawn features neatly trimmed grass and colorful flowerbeds. Large front windows allow for natural light, framed by light-colored siding underneath a gabled roof.

4.94 out of 5 average rating, 133 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.

An open concept living area features a plush gray sofa with accent pillows, complemented by a modern coffee table on a textured area rug. The kitchen area includes wooden cabinets and bar seating, while natural light brightens the space through a nearby window.

5 out of 5 average rating, 183 reviews

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.

The exterior of the Cozy Cottage is presented, showcasing a two-story structure with blue shutters and flower boxes. A set of wooden stairs leads to the entrance, which is framed by a tree that provides shade. The surrounding yard features green grass and a pathway.

4.95 out of 5 average rating, 201 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 spacious living area features a large flat-screen television mounted on a dark wall. Two light gray sofas are arranged around a round coffee table on a textured rug. Soft lighting from two side tables complements the warm wooden flooring.

4.99 out of 5 average rating, 181 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.

4.91 out of 5 average rating, 534 reviews

The entrance to the cabin is framed by wooden siding, featuring a central door adorned with a seasonal wreath. Natural elements, including pumpkins, are arranged on a small porch flanked by rustic decorations and a wooden fence made of branches.

Cabin in Dixon

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.

4.97 out of 5 average rating, 419 reviews

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.

Superhost

A spacious kitchen features wooden cabinets and a granite countertop island. Four wooden dining chairs surround a rectangular table. A door leads outside, and natural light enters through two windows dressed with light curtains.

Holiday home in Owensboro

4.9 out of 5 average rating, 151 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.

Popular amenities for Owensboro outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

The living area features a spacious gray sofa with blue accent pillows, complemented by a circular wooden dining table. Two lamps provide soft lighting, and wall art adds visual interest. Large windows are dressed with light curtains, allowing natural light to fill the room.

4.93 out of 5 average rating, 85 reviews

Comfortable 2 bedroom with 2 private baths, patio.

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.

4.91 out of 5 average rating, 96 reviews

Hill Ave home

5 out of 5 average rating, 36 reviews

A peaceful countryside scene features rolling hills and a clear pond surrounded by trees. Bare branches indicate the changing seasons, while a vibrant blue sky is dotted with soft clouds, creating a serene backdrop of nature.

Home in Olaton

Cowbell Cottage farm stay

4.96 out of 5 average rating, 156 reviews

A cozy living area is highlighted by a Christmas tree adorned with red and silver ornaments. Comfortable seating includes an orange chair and a spacious sofa, with festive decor and warm lighting creating a welcoming space for gatherings. A large flat-screen TV is mounted on the wall.

Home in Santa Claus

Christmas Cottage

4.99 out of 5 average rating, 78 reviews

Blue Moon Cottage: Music Room, Inground Pool

4.92 out of 5 average rating, 130 reviews

A modern living area features a brown leather sectional sofa complemented by a patterned area rug. A wooden coffee table sits at the center, surrounded by decorative pillows. Large windows allow natural light to fill the space, while artwork adorns the walls.

Home in Newburgh

Bourbon Escape

4.96 out of 5 average rating, 168 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

5 out of 5 average rating, 50 reviews

A covered porch features wooden flooring and a railing made of vertical wooden posts. Two blue chairs and a small table are arranged for outdoor seating. Lush greenery is visible in the background, enhancing the serene outdoor atmosphere.

Home in Calhoun

The Nest

Apartment rentals with outdoor seating

4.83 out of 5 average rating, 18 reviews

The living area features a mix of vintage-style furniture, including two brown leather sofas and a coffee table. A flat-screen television is mounted above a fireplace. The walls are adorned with framed artwork, reflecting a 1990s theme, and warm wooden flooring complements the space.

Apartment in Newburgh

Downtown Newburgh 2BR - Near Riverfront & Hospital

4.94 out of 5 average rating, 77 reviews

A four-poster bed with a floral patterned duvet is positioned against a light grey wall, complemented by two decorative pillows. Soft lighting from a bedside lamp creates a cozy ambiance, while yellow curtains frame the window, adding warmth to the space.

Apartment in Henderson

Suburban Chateau

Apartment in Downtown Evansville

A modern kitchen features wooden cabinetry with under-cabinet lighting. Stainless steel appliances, including a gas stove and refrigerator, are present. A central island with seating for two adds functionality, while hardwood flooring complements the space. Ductwork is visible along the ceiling.

4.89 out of 5 average rating, 19 reviews

Studio with a View

Superhost

Apartment in Evansville

4.85 out of 5 average rating, 503 reviews

Refuge at the River--Greenway/Bike path steps away

4.89 out of 5 average rating, 265 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

4.95 out of 5 average rating, 253 reviews

A historic brick building stands on a cobblestone street, framed by mature trees and shrubs. The entrance features a set of stairs leading to double doors adorned with decorative glass. A lamppost adds charm to the inviting outdoor space.

Apartment in Evansville

Victorian 1 Bedroom Guesthouse Apt on 1st Street

4.99 out of 5 average rating, 86 reviews

A spacious deck features a table and several chairs, providing an ideal space for outdoor dining. Lush trees frame the view of the Ohio River in the background, where calm waters reflect the sky. The setting offers a serene environment for relaxation.

Apartment in Owensboro

River House Suite

Apartment in Madisonville

An inviting living area showcases exposed brick walls and a mix of modern and vintage furnishings. A plush brown sofa is set opposite a pair of accent chairs. A colorful area rug adds warmth to the space, while a contemporary light fixture illuminates the room.

4.85 out of 5 average rating, 20 reviews

“Executive on Main”

Condo rentals with outdoor seating

A cozy living area is showcased with a dark gray couch adorned with several plush pillows. A small marble and wood coffee table sits on a decorative rug, complemented by a stylish accent chair. Natural light enters through draped windows, enhancing the space's comfort.

5 out of 5 average rating, 35 reviews

East Side Gem: 2BR Near Hospitals & Dining

An indoor arcade space features a Skee-Ball machine and basketball game along with various arcade consoles positioned next to a cozy sleeping area, which includes a spacious bed and a large television. Soft lighting illuminates the relaxed atmosphere.

4.77 out of 5 average rating, 13 reviews

Arcade+Patio+Newly Renovated

5 out of 5 average rating, 32 reviews

A collage of a modern townhome featuring a white bed with decorative pillows, a stylish living space with a flat-screen TV, and a serene bathroom with a walk-in shower. An outdoor seating area is shown with a fire pit, inviting relaxation.

Condo in Owensboro

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

5 out of 5 average rating, 6 reviews

Haynie's Corner Vintage

A spacious living area is furnished with a dark leather sofa and a coffee table. A ceiling fan provides ventilation, and light floods through sliding glass doors that open to a balcony. A dining area is visible in the background, completing the inviting layout.