Holiday Rentals in Kentucky

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Kentucky holiday rentals
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Best Holiday rentals and Airbnb offers in Kentucky

Best family friendly Kentucky holiday rentals

Among the 19189 accommodations in Kentucky, here are the 4 best family friendly rentals

Charming 3-bedroom House "Cavern" With Tons Of Amenities In Cave City. - Kentucky
9.6 20 reviews
Kentucky
02/10 – 03/10
SG$381/nightfor 1 night

Charming 3-bedroom House "Cavern" With Tons Of Amenities In Cave City.

3 10
apartment , Cave City
This Cave City holiday home, "Cavern", is centrally located in Cave City, Kentucky, offering easy access to Mammoth Cave National Park and attractions such as the Mammoth Cave Wildlife Museum and Dinosaur World.
Sleeping up to 10 guests in three bedrooms (king, queen, and bunk beds) plus a sofa bed, the property boasts a kitchen with fridge, microwave, and dishwasher, a bathroom with hairdryer, a dedicated office space, and a terrace/balcony plus garden.
Capital City Condo #10 - Kentucky
8.4 8 reviews
Kentucky
03/07 – 04/07
SG$212/nightfor 1 night

Capital City Condo #10

1 2
apartment , Frankfort
Capital City Condo #10, a one-bedroom apartment in Frankfort, Kentucky, offers convenient access to attractions such as the Kentucky Governor's Mansion and the Rebecca Ruth Candy Museum, with their precise distances needing further clarification.
This self-catering flat sleeps two guests and features a balcony, Wi-Fi, a Smart TV, and air conditioning, alongside essential amenities; nearby, explore Parque Cove Spring and the Audubon Center and Buckley Wildlife Sanctuary.
La Casa Delle Pesche - Kentucky
9.2 7 reviews
Kentucky
03/07 – 05/07
SG$113/nighttotal: SG$226 (2 )

La Casa Delle Pesche

1 2
house , Georgetown
La Casa delle Pesche, a Georgetown, Kentucky property, is situated 24 kilometres from Blue Grass Airport.
This two-bedroom house, boasting 167 square metres of floor space, comfortably accommodates seven guests and includes a fully equipped kitchen, private garden, free parking, and Wi-Fi.
Lake Front Cabin - Private Dock - Kentucky
9.7 112 reviews
Kentucky
13/09 – 20/09
SG$206/nighttotal: SG$1442 (7 )

Lake Front Cabin - Private Dock

1 2
cabin , Burnside
This Burnside A-frame cottage is situated in the Echo Point neighbourhood on Cumberland's South Fork, a 24km drive from Burnside town and its shops.
Sleeping up to five guests in two bedrooms and one bathroom, this pet-friendly lodge boasts a private dock, access to a boat ramp, and a relaxing back deck with lake views; a fridge, freezer, microwave, air conditioning and Wi-Fi are also included.

Top cities

Best pet friendly Kentucky holiday rentals

Among the 19189 accommodations in Kentucky, here are the 4 best pet friendly rentals

On 220 Acres! Hot Tub Haven In West Liberty - Kentucky
10 3 reviews
Kentucky
03/07 – 05/07
SG$530/nighttotal: SG$1060 (2 )

On 220 Acres! Hot Tub Haven In West Liberty

4 12
house , West Liberty
This West Liberty holiday home is situated approximately 117 kilometres from Tri-State Airport, in a region requiring further specification for precise proximity to local attractions.
The 186-square-metre property boasts four bedrooms, three bathrooms, sleeps 27 guests, and includes a fully equipped kitchen, Wi-Fi, laundry facilities, parking, and a garden.
Peaceful Private 3 Br New Home Near Mammoth Cave. - Kentucky
9.8 71 reviews
Kentucky
25/07 – 26/07
SG$266/nightfor 1 night

Peaceful Private 3 Br New Home Near Mammoth Cave.

3 4
apartment , Cave City
This Cave City holiday home, a three-bedroom property sleeping seven, is located 5-8 km from Mammoth Cave National Park, offering easy access to the Mammoth Cave Visitor Centre, Mammoth Cave Wildlife Museum, and Kentucky Repertory Theatre.
The self-catering house boasts a fully equipped kitchen, including a fridge, microwave, and dishwasher, plus a garden, parking, and air conditioning; guests can enjoy TVs in each bedroom and outdoor space with a covered porch and back deck with barbecue.
Mayor's Family House Hot Tub, Piano & 2 Kitchens - 5 Minutes To Ark - Sleeps 16+ - Kentucky
9.6 35 reviews
Kentucky
02/10 – 03/10
SG$896/nightfor 1 night

Mayor's Family House Hot Tub, Piano & 2 Kitchens - 5 Minutes To Ark - Sleeps 16+

4 10
apartment , Williamstown
This Williamstown holiday home, situated within 3.2km of the William Arnold Log House and Webb Park, and 4.2km from the Ark Encounter, offers convenient access to local attractions.
The 279 square metre property boasts four bedrooms, three bathrooms, sleeps eighteen guests, and includes a Jacuzzi, tennis court, and fully equipped kitchen with free Wi-Fi.
Cozy Mountain Cabin Near Red River Gorge, Hollerwood And More! Pet Friendly - Kentucky
9.8 10 reviews
Kentucky
27/06 – 04/07
SG$197/nighttotal: SG$1379 (7 )

Cozy Mountain Cabin Near Red River Gorge, Hollerwood And More! Pet Friendly

1 2
cabin , Stanton
The Mountain Laurel cabin, a self-catering retreat near Stanton, Kentucky, sits on 10 private acres (approximately 4 hectares) within the Daniel Boone National Forest, minutes from attractions such as the Red River Gorge and Natural Bridge State Park.
This one-bedroom lodge offers 60 square metres of living space, sleeping up to four guests, and boasts a fully equipped kitchen including a dishwasher, a garden, air conditioning, and covered porches; complimentary amenities include bath soap, oatmeal, tea, and sweeteners, plus on-site hiking opportunities and a gas grill.

Frequently asked questions about holiday rentals in Kentucky

  • What are the must-see sights in Kentucky, United States?

    Kentucky offers a fantastic mix of attractions. For history buffs, Mammoth Cave National Park, the world's longest known cave system, is a must-see, along with the Shaker Village of Pleasant Hill, showcasing a preserved 19th-century Shaker community. Louisville's Muhammad Ali Center celebrates the life and legacy of the boxing legend, while Churchill Downs, home to the Kentucky Derby, is iconic. Frankfort, the state capital, boasts the Kentucky State Capitol building and the Old State House.
  • What are the best Airbnb and vacation rentals in Kentucky?

  • What are the vacation rentals like in Kentucky?

    If you're considering a vacation rental in Kentucky, you'll be pleased to know that there are many types of vacation rentals on offer. You can book into a house, apartment, villa, bungalow, or loft. You'll be sure to find the right vacation rental for your needs. Yes! You can stay in an unusual vacation rental in Kentucky, like a converted barn, a treehouse, a yurt, a tipi, or even a historic mansion.
  • Are there any unique natural phenomena in Kentucky, United States?

    Absolutely! Mammoth Cave's vast underground network is a geological wonder. Red River Gorge, with its stunning sandstone arches and cliffs, offers incredible hiking and rock climbing opportunities. The unique landscape of the Cumberland Plateau, with its diverse flora and fauna, is another highlight.
  • What are the most popular Airbnbs in Kentucky?

  • Can you find any unique vacation rentals in Kentucky?

    Try a Hot Brown, an open-faced sandwich topped with turkey covered with a cheesy mornay sauce, bacon, and tomato (all toasted under a broiler and served hot). You'll also want to try some spoonbread, a moist corn souffle that's said to be a Native American dish. For something sweet, try the Derby Pie, an iconic chocolate-walnut pie.
  • What essentials should you bring to Kentucky, United States?

    Comfortable walking shoes are a must, especially if you plan on exploring caves or hiking. Layers of clothing are recommended as Kentucky's weather can be unpredictable. Sunscreen, insect repellent, and a hat are also advisable, particularly during warmer months. A reusable water bottle will be useful, especially while exploring outdoors.
  • What are the best vacation rentals with a pool in Kentucky?

  • What dishes should you try in Kentucky?

    The best time to visit Kentucky is between April and June, and in the fall months between August and September.Well, you can swig bourbon and watch horse racing, but there is so much more to do in Kentucky. Go see some live music, maybe take in a Bluegrass concert, drink some craft beer or eat some great food, delve into history, go caving or explore the great outdoors. There's plenty to keep you occupied!
  • What famous events or festivals are happening in Kentucky, United States?

    The Kentucky Derby, held annually at Churchill Downs in Louisville, is internationally renowned. The Kentucky State Fair, a large agricultural fair, takes place in Louisville each autumn. Numerous smaller, regional festivals celebrating Kentucky's heritage and culture occur throughout the year. For example, the Fancy Farm Picnic, a political event with a unique atmosphere, is a long-standing tradition.
  • What are the best rentals for families and kids in Kentucky?

  • When is the best time to go to Kentucky?

    The best time to visit Kentucky is between April and June, and in the fall months between August and September.
  • Where can you find the best restaurants serving local dishes in Kentucky, United States, and what are the must-try specialties?

    For authentic Kentucky cuisine, try the restaurants in Louisville's NuLu neighbourhood or explore eateries in Lexington's Distillery District. Must-try dishes include Kentucky burgoo (a hearty stew), hot brown (a creamy turkey casserole), and bourbon balls (chocolate-covered bourbon-infused sweets). Many restaurants also offer variations of fried chicken and barbecue.
  • What are the best rentals or Airbnbs with a jacuzzi in Kentucky?

  • What can you do in Kentucky?

    Well, you can swig bourbon and watch horse racing, but there is so much more to do in Kentucky. Go see some live music, maybe take in a Bluegrass concert, drink some craft beer or eat some great food, delve into history, go caving or explore the great outdoors. There's plenty to keep you occupied!
  • What are some less-famous attractions in Kentucky, United States that are worth a visit?

    The Abraham Lincoln Birthplace National Historical Park in Hodgenville offers a glimpse into the early life of the 16th US president. The Cumberland Falls State Resort Park, known for its moonbow, a rare lunar rainbow, is a hidden gem. My Old Kentucky Home State Park in Bardstown, with its beautiful architecture and historical significance, is another worthwhile destination.
  • What are the best activities for engaging with locals and understanding their culture in Kentucky, United States?

    Visiting local farmers' markets provides a chance to interact with producers and sample regional produce. Attending smaller, community festivals and events offers opportunities to meet locals and experience Kentucky's culture firsthand. Exploring smaller towns and engaging in conversations with residents in local establishments can also offer valuable insights.
  • What unique natural landscapes and terrain features can travellers explore in Kentucky, United States?

    Kentucky boasts diverse landscapes. The rolling hills of the bluegrass region contrast sharply with the rugged terrain of the Red River Gorge and the cavernous depths of Mammoth Cave. The Mississippi River also forms a significant part of the state's western border, offering scenic views and opportunities for river-based activities.
  • How many days are ideal for a trip to Kentucky, United States, and what are some itinerary suggestions?

    Seven to ten days allows for a good exploration of Kentucky's highlights. A possible itinerary could include: days 1-3 exploring Louisville (Muhammad Ali Center, Churchill Downs, bourbon distilleries), days 4-5 at Mammoth Cave National Park, days 6-7 in the Red River Gorge, and a final day in Lexington before departure. This is just a suggestion, and itineraries can be adjusted based on interests.

Nearby regions

Best Kentucky holiday rentals with a pool

Among the 19189 accommodations in Kentucky, here are the 4 best rentals with a pool

Pool*pickleball Bldg*hottub*speakeasy*bourbontrail - Kentucky
10 88 reviews
Kentucky
03/07 – 05/07
SG$2841/nighttotal: SG$5682 (2 )

Pool*pickleball Bldg*hottub*speakeasy*bourbontrail

1 12
apartment , Mount Washington
This Bourbon Barrel Retreat near Mount Washington, Kentucky offers five bedrooms and three bathrooms sleeping twelve guests, situated a short drive from Bardstown, Louisville, and Lexington, providing easy access to distilleries, wineries and state parks such as My Old Kentucky Home State Park (approximately 40km away).
The property boasts two unique on-site buildings: a Bourbon Speakeasy and a Pickleball Sports Lounge, alongside a 9-metre pool, hot tub, extensive outdoor space including a fire pit and Blackstone grill, plus a fully equipped kitchen and high-speed Wi-Fi throughout.
Spacious Nulu 1br Cozysuites 05 - Kentucky
Kentucky
08/08 – 15/08
SG$167/nighttotal: SG$1169 (7 )

Spacious Nulu 1br Cozysuites 05

1 2
apartment , Louisville
This two-bedroom flat is located in Downtown Louisville, a short walk from Nulu Market Place and Louisville Slugger Field, offering convenient access to local attractions.
With a floor area of 60 square meters, this accommodation for up to three guests includes a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, on-site parking, a shared swimming pool, and a garden.
Remodeled Lakefront Woodson Bend Condo- 92-2 Eagle Drive - Kentucky
9.8 23 reviews
Kentucky
04/08 – 08/08
SG$472/nighttotal: SG$1888 (4 )

Remodeled Lakefront Woodson Bend Condo- 92-2 Eagle Drive

3 7
apartment , Burnside
This waterfront apartment is located near Burnside, Kentucky, within 20 kilometres of Burnside Marina, Daniel Boone National Forest, and Cumberland River, offering stunning views and easy access to water activities. The apartment has excellent user ratings.
The property has 3 bedrooms, ideal for families or groups of friends, and can comfortably accommodate up to 9 guests. Amenities include free Wi-Fi, a patio, a fireplace, a fully equipped kitchen, a swimming pool, and a garden, providing everything you need for a relaxing and enjoyable stay.
Whispering Woods Cottage | Hot Tub | Pool - Kentucky
9.8 97 reviews
Kentucky
09/07 – 15/07
SG$250/nighttotal: SG$1500 (6 )

Whispering Woods Cottage | Hot Tub | Pool

1 1
cabin , Burnside
Whispering Woods, a lakeside cottage within the Lake Cumberland Resort community near Burnside, Kentucky, offers easy access to three community swimming pools and a tennis court.
This one-bedroom cottage sleeps two, boasting a fully equipped kitchen (fridge, freezer, microwave, dishwasher), a private hot tub (additional cleaning fee applies), a smart TV, and air conditioning, all within a gated community with 24-hour security.

Best Kentucky holiday rentals with parking

'Grandma's Farm House' On 125 Acres W/ Fire Pit! - Kentucky
10 140 reviews
Kentucky
06/08 – 09/08
SG$275/nighttotal: SG$825 (3 )

'Grandma's Farm House' On 125 Acres W/ Fire Pit!

2 4
house , Beattyville
This house is located just 19 miles from Bear Track Park in Beattyville, offering a secluded and peaceful getaway on 125 acres. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The property features two bedrooms and one bathroom, accommodating up to six guests comfortably within its 121 square metres of space. Guests can enjoy a fully equipped kitchen, a cozy outdoor fire pit, and free Wi-Fi access throughout the house.
Log Cabin, 5 Miles From Town, But Very Country Setting - Kentucky
9.7 289 reviews
Kentucky
06/08 – 09/08
SG$163/nighttotal: SG$489 (3 )

Log Cabin, 5 Miles From Town, But Very Country Setting

2 4
apartment , Science Hill
This family-friendly holiday home is located in a peaceful rural area near Science Hill, Kentucky, just 14.5 kilometres from SomerSplash and 19.3 kilometres from Cave Hill Vineyard. The property has received excellent ratings for its cleanliness, location, and overall user experience.
The 84 square metre property has two bedrooms, one bathroom, and can accommodate up to seven guests. You'll enjoy a fully equipped kitchen, a private garden, a swimming pool, and a terrace, perfect for relaxing and enjoying the Kentucky countryside.
Bluegrass Retreat With Hot Tub! Near Horse Park! - Kentucky
9.9 137 reviews
Kentucky
04/10 – 21/10
SG$654/nighttotal: SG$11118 (17 )

Bluegrass Retreat With Hot Tub! Near Horse Park!

3 6
apartment , Lexington-Fayette
This apartment is located in Central Kentucky, just a short drive from Lexington's downtown, the Kentucky Horse Park, Keeneland, and the Ark Encounter. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The three-bedroom home comfortably accommodates up to six guests and features a well-equipped kitchen, a relaxing outdoor space with a hot tub, and a range of amenities including a Smart TV, a computer desk, and a two-car garage.
The Rustic Suite On Bourbon Trail - Kentucky
9.6 33 reviews
Kentucky
25/07 – 26/07
SG$216/nightfor 1 night

The Rustic Suite On Bourbon Trail

1 4
apartment , Loretto
This newly constructed suite in Loretto is situated approximately 3.5 kilometres from the Abbey of Gethsemani and the Kentucky Railway Museum, providing convenient access to My Old Kentucky Home State Park and Graham Memorial Park.
This 48 square metre apartment accommodates up to four guests, featuring one bedroom with a king-size bed and a loft sleeping area, a fully equipped kitchen, a luxurious bathroom with a dual-head shower, and a terrace or balcony, with parking available for large trailers upon advance notice.
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