Holiday rentals in Island

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Top-rated holiday rentals in Island

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Top guest favourite
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
4.95 out of 5 average rating, 365 reviews

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.

Superhost
A charming tiny home is set against a backdrop of lush greenery. The exterior features a welcoming front porch with two rocking chairs positioned on either side of the entrance, inviting moments of relaxation. A large tree provides shade and adds to the overall serene ambiance.
Tiny home in Beaver Dam
4.86 out of 5 average rating, 43 reviews

A Cozy Kentucky Retreat w/ Fishing and boating

Nestled in the serene countryside, our cozy tiny home offers the perfect escape just minutes from town. Enjoy the tranquility of nature while casting a line into the peaceful pond, complete with fishing poles to rent for your convenience. Unwind by the campfire under the stars, sharing stories and savoring the warmth of the flames. This charming retreat is ideal for those seeking a blend of comfort and adventure, making it the perfect getaway in the heart of Kentucky’s beautiful landscape.

Top guest favourite
A rustic log cabin is set against a backdrop of greenery, with a large Osage Orange tree providing shade. The cabin features a combination of natural wood exteriors and a modern addition, showcasing a warm and inviting entrance surrounded by well-maintained landscaping.
Cabin in Utica
5 out of 5 average rating, 32 reviews

Rustic Log Cabin Old Farm

Step back in time at this 1800s log cabin on historic DeLacey Farm. Surrounded by barns, wildlife, and wide-open fields, this rustic getaway sits on a nearly 100-year-old working farm—just minutes from Owensboro’s BBQ, bourbon, and small-town charm. Relax on the back deck with views of the original farm buildings, or head into town to explore the Green River Distillery and local eats. It’s the perfect blend of peaceful retreat and convenient access to everything Owensboro has to offer.

Guest favourite
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.
Home in Owensboro
4.93 out of 5 average rating, 137 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.

Guest favourite
The exterior of the home features a welcoming front porch with steps leading up to the entrance, framed by white railing. The facade is adorned with large windows and traditional shutters, complemented by a red roof that adds a pop of color.
Home in Calhoun
5 out of 5 average rating, 17 reviews

Calhoun Riverview House

Escape to this cozy riverside getaway in Calhoun, Kentucky! Nestled along the beautiful Green River, our two-bedroom, one-bath home offers a peaceful retreat surrounded by nature. Enjoy your morning coffee on the deck while taking in river views. With a fully equipped kitchen and comfortable living area this home is perfect for couples, friends, or small families looking for a serene stay. Book your stay at our Riverside Retreat and experience all that Calhoun has to offer!

Top guest favourite
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
4.91 out of 5 average rating, 552 reviews

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.

Top guest favourite
A cozy cabin stands surrounded by a well-maintained lawn, with three large windows adorning its bright red exterior. Lush greenery frames the structure, while a screened-in porch is visible, providing a serene view of the landscape. Tall trees offer shade nearby.
Cabin in Calhoun
4.93 out of 5 average rating, 43 reviews

Little Red on the Green River

Little Red on the Green is the perfect getaway if you enjoy the peacefulness of watching the river flow downstream. This simple, cute, cozy, 600 square foot, one room cabin is sure to be enjoyed. The private riverfront property is just steps from the river bank. If you like to fish, this might be the perfect spot! Calhoun boat ramp is only 2 miles away. This property is centrally located, 25 miles north-east of Madisonville, 20 miles south of Owensboro.

Top guest favourite
The kitchen features a U-shaped countertop with wooden cabinetry and a deep sink, complemented by a tile backsplash. A dining area with a round table and chairs is visible in the background, along with a decorative wall piece and clock adding subtle detail to the space.
Farm stay in Hopkinsville
4.86 out of 5 average rating, 150 reviews

Quiet country setting.

Hello! Thank you for considering staying with us during your stay in or around Hopkinsville, Ky. Whether you’re coming for work, pleasure or, to visit family, we think you’ll love staying here. It’s a warm and inviting home, with all the amenities you need for the perfect stay. We live on the farm, and will be around if you require anything during your stay. Please email if you have any questions. We look forward to hearing from you.

Top guest favourite
Cottage in Owensboro
4.97 out of 5 average rating, 428 reviews

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
Home in Livermore
5 out of 5 average rating, 3 reviews

Two Rivers Retreat

Welcome to Two Rivers Retreat – Your Serene Escape in Livermore, KY! Nestled in the heart of Livermore, where the Green and Rough Rivers meet, our cozy two-bedroom home offers the perfect blend of comfort, style, and natural charm. Whether you're here to explore the local rivers, visit with family/friends, attend a community event, or simply enjoy a peaceful getaway, Two Rivers Retreat is your ideal home away from home.

Guest favourite
The front yard features a well-maintained lawn with freshly mulched landscaping. Two flowering plants are arranged neatly in the garden, while a charming walkway leads to the front porch. Decorative lanterns are positioned near the entrance, enhancing the welcoming atmosphere.
Home in Central City
5 out of 5 average rating, 13 reviews

Guitars & Harmony

Daddy, want you take me back to Muhlenberg County…this gem is located in the heart of the Western Kentucky Coalfield. Guitars & Harmony is a charismatic, completely furnished cottage house. It encompasses two queen bedrooms and two full bathrooms, along with a fully stocked kitchen and charming family area. Each room echoes the rich, traditional, musical heritage that makes Muhlenberg County so unique.

Guest favourite
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
4.96 out of 5 average rating, 181 reviews

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. 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.

Popular amenities for Island holiday rentals

  1. Airbnb
  2. United States
  3. Kentucky
  4. McLean County
  5. Island