15280+ Vacation Rentals Near Kentucky |
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Big Island Hawaii Rental - Vacation Rentals in Kentucky

Charming Farm Cottage view Horses + City Access - Near Bourbon Trail Keeneland From US $243
         

10.0 (296 Reviews)
Cottage
Charming Farm Cottage view Horses + City Access - Near Bourbon Trail Keeneland
  • Air Conditioner
  • Parking
  • Pet Friendly

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Prickly Pair Suites From US $137
         

8.2 (49 Reviews)
House
Prickly Pair Suites
  • Air Conditioner
  • Parking
  • Internet

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Pillow and Paddock B&B From US $374
         

|
10.0 (52 Reviews)
Bed & Breakfast
Pillow and Paddock B&B
  • Designated Smoking Area
  • TV
  • Balcony/Terrace

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Renovated Train Station on Thoroughbred Horse Farm From US $256
         

10.0 (286 Reviews)
House
Renovated Train Station on Thoroughbred Horse Farm
  • Air Conditioner
  • Parking
  • Pool

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The Barn at Deva's Farm: Haute Blue Grass - Chill Retreat in the countryside From US $196
         

10.0 (260 Reviews)
House
The Barn at Deva's Farm: Haute Blue Grass - Chill Retreat in the countryside
  • Air Conditioner
  • Parking
  • Pool

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The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands From US $376
         

10.0 (179 Reviews)
House
The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands
  • Air Conditioner
  • Parking
  • TV

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Authentic, Rustic, Historic Log Cabin From US $546
         

10.0 (165 Reviews)
House
Authentic, Rustic, Historic Log Cabin
  • Air Conditioner
  • Parking
  • TV

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Riverfront retreat. Stunning view. Dock. 20 minutes to downtown Louisville. From US $656
         

10.0 (157 Reviews)
House
Riverfront retreat. Stunning view. Dock. 20 minutes to downtown Louisville.
  • Air Conditioner
  • Parking
  • TV

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Luxury Places to Stay in Kentucky

Over 10000+ Luxury Places to Stay in or Near Kentucky
New
House
NEW - 29 Acre Private Hilltop Resort - Bourbon Trail - Heated Pool - Pickleball
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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New
House
Luxury Living, Derby Thrills
  • Air Conditioner
  • Parking
  • Pool

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Entire Main St. Building · Entire Downtown Building w/7 suites! By Hollyhock From US $9,995
         

New
Apartment
Entire Main St. Building · Entire Downtown Building w/7 suites! By Hollyhock
  • Air Conditioner
  • TV
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6-acre retreat in Derby City near Valhalla and Bourbon Trail From US $9,600
         

10.0 (1 Review)
House
6-acre retreat in Derby City near Valhalla and Bourbon Trail
  • Air Conditioner
  • Parking
  • Designated Smoking Area

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Historic, Luxury House in Prime Location From US $9,485
         

10.0 (1 Review)
House
Historic, Luxury House in Prime Location
  • Air Conditioner
  • Parking
  • TV

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House of David From US $8,940
         

8.8 (5 Reviews)
Apartment
House of David
  • Air Conditioner
  • Parking
  • Pet Friendly

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Celebrity Host Home. Best Derby Location! From US $8,044
         

10.0 (3 Reviews)
House
Celebrity Host Home. Best Derby Location!
  • Air Conditioner
  • Parking
  • TV

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Derby City's Finest - Luxury Home in the heart of historic Crescent Hill From US $7,918
         

New
House
Derby City's Finest - Luxury Home in the heart of historic Crescent Hill
  • Air Conditioner
  • Parking
  • TV

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Top-Rated Vacation Rentals with a Pool in Kentucky

Over 2018+ Top-Rated Vacation Rentals with a Pool in or Near Kentucky
A Cozy Cottage Near the Heart of All Louisville Attractions! From US $190
         

10.0 (393 Reviews)
Cabin
A Cozy Cottage Near the Heart of All Louisville Attractions!
  • Air Conditioner
  • Parking
  • Pool

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Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail From US $210
         

10.0 (240 Reviews)
Cottage
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail
  • Air Conditioner
  • Parking
  • Pool

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Newly remodeled! Holland Farms is located in the Golden Triangle of Northern KY! From US $1,111
         

10.0 (169 Reviews)
House
Newly remodeled! Holland Farms is located in the Golden Triangle of Northern KY!
  • Air Conditioner
  • Parking
  • Pool

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Lakehouse Hot tub & pool near Ark Encounter From US $353
         

10.0 (161 Reviews)
House
Lakehouse Hot tub & pool near Ark Encounter
  • Air Conditioner
  • Parking
  • Pool

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Parklike Estate in the Heart of Louisville w/Pool and Gardens - Family Friendly From US $1,207
         

10.0 (151 Reviews)
House
Parklike Estate in the Heart of Louisville w/Pool and Gardens - Family Friendly
  • Air Conditioner
  • Parking
  • Pet Friendly

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Luxurious Suite w/Garden on Court Square Downtown From US $175
         

10.0 (132 Reviews)
Hotel
Luxurious Suite w/Garden on Court Square Downtown
  • Air Conditioner
  • Parking
  • Pool

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1of2 Bedroom Suites at Lake Barkley Old Kuttawa, KY - w/golf cart From US $153
         

10.0 (130 Reviews)
House
1of2 Bedroom Suites at Lake Barkley Old Kuttawa, KY - w/golf cart
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  • Parking
  • Pool

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Pool | Hot Tub | Covered Porch | Patio | Game Room From US $997
         

10.0 (124 Reviews)
House
Pool | Hot Tub | Covered Porch | Patio | Game Room
  • Air Conditioner
  • Parking
  • Pet Friendly

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Pet-Friendly Vacation Rentals in Kentucky

Over 5461+ Pet-Friendly Vacation Rentals in or Near Kentucky
KY Lake Arts & Crafts Cedar Shake Home/On-site Boat Rentals with Private Dock From US $318
         

10.0 (129 Reviews)
House
KY Lake Arts & Crafts Cedar Shake Home/On-site Boat Rentals with Private Dock
  • Air Conditioner
  • Parking
  • Pet Friendly

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Steps from Downtown UK / Transylvania University From US $154
         

|
7.7 (3 Reviews)
Apartment
Steps from Downtown UK / Transylvania University
  • Air Conditioner
  • Parking
  • Pet Friendly

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Aloft by Marriott Louisville Downtown From US $131
         

|
9.0 (1004 Reviews)
Hotel
Aloft by Marriott Louisville Downtown
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Martin House - In the heart of historic downtown Lexington From US $435
         

10.0 (101 Reviews)
House
The Martin House - In the heart of historic downtown Lexington
  • Air Conditioner
  • Parking
  • Pet Friendly

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Lake Front Home with community boat ramp. Private, close to marinas and town. From US $180
         

9.6 (243 Reviews)
Cottage
Lake Front Home with community boat ramp. Private, close to marinas and town.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Charming & Inviting Apartment in Historic Downtown Paris, Ky. From US $106
         

9.8 (123 Reviews)
Apartment
Charming & Inviting Apartment in Historic Downtown Paris, Ky.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Cozy Studio home 10min from Murray and 20min from Ky Lake From US $187
         

9.8 (114 Reviews)
House
Cozy Studio home 10min from Murray and 20min from Ky Lake
  • Air Conditioner
  • Parking
  • Pet Friendly

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Dale Hollow Cabin Next To State Park With Free Fire Pit & COVERED Boat Slip From US $266
         

9.8 (86 Reviews)
House
Dale Hollow Cabin Next To State Park With Free Fire Pit & COVERED Boat Slip
  • Air Conditioner
  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in Kentucky

Over 3035+ Large Vacation Homes & Villas in or Near Kentucky
Rough River Lake House conveniently located by Axtel Marina and Nicks Boat Dock From US $364
         

9.8 (127 Reviews)
House
Rough River Lake House conveniently located by Axtel Marina and Nicks Boat Dock
  • Air Conditioner
  • Parking
  • TV

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Mint House at 800 Tower - Louisville From US $210
         

|
7.6 (79 Reviews)
Apartment
Mint House at 800 Tower - Louisville
  • Air Conditioner
  • Wheelchair Accessible
  • Balcony/Terrace

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Bourbon Trail, Buffalo Trace, Downtown Frankfort From US $475
         

10.0 (41 Reviews)
House
Bourbon Trail, Buffalo Trace, Downtown Frankfort
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Riverview Log Cabin Lodge Near Creation Museum & Arc Encounter From US $818
         

9.8 (203 Reviews)
Cabin
Riverview Log Cabin Lodge Near Creation Museum & Arc Encounter
  • Air Conditioner
  • Parking
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Wild Vines Log Cabin .5miles from Ky Lake, Hot Tub, Pool Table, 1500sqft Venue! From US $693
         

9.8 (93 Reviews)
House
Wild Vines Log Cabin .5miles from Ky Lake, Hot Tub, Pool Table, 1500sqft Venue!
  • Air Conditioner
  • Parking
  • Pet Friendly

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All You Need and More! From US $799
         

9.6 (123 Reviews)
House
All You Need and More!
  • Air Conditioner
  • TV
  • Balcony/Terrace

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The Highlands Hangout, EXPO, DOWNTOWN, restaurant row! Game room & LOCATION! From US $950
         

9.8 (38 Reviews)
House
The Highlands Hangout, EXPO, DOWNTOWN, restaurant row! Game room & LOCATION!
  • Air Conditioner
  • Parking
  • TV

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6 King Beds | Hot Tub | Highlands Mansion From US $2,141
         

10.0 (118 Reviews)
House
6 King Beds | Hot Tub | Highlands Mansion
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  • Parking
  • TV

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Wheelchair Accessible Vacation Homes in Kentucky

Over 1820+ Wheelchair Accessible Vacation Homes in or Near Kentucky
Welcome to the River City Loft! From US $186
         

10.0 (175 Reviews)
Condo
Welcome to the River City Loft!
  • Air Conditioner
  • Parking
  • TV

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Lexington Family Home about 2 Miles to UK Campus! From US $136
         

|
9.3 (3 Reviews)
House
Lexington Family Home about 2 Miles to UK Campus!
  • Parking
  • Wheelchair Accessible
  • Child Friendly

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Drury Inn & Suites Louisville North From US $118
         

|
9.6 (1005 Reviews)
Hotel
Drury Inn & Suites Louisville North
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  • Parking
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Sunrise Cabin- Hot Tub, WiFi, Firepit, Grill From US $143
         

9.4 (284 Reviews)
Cabin
Sunrise Cabin- Hot Tub, WiFi, Firepit, Grill
  • Air Conditioner
  • Parking
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Luxurious 2BR/2Bath with Outdoor Courtyard and Garage in Downtown Bardstown From US $309
         

10.0 (248 Reviews)
House
Luxurious 2BR/2Bath with Outdoor Courtyard and Garage in Downtown Bardstown
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  • Parking
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Welcome to Derby City Loft! From US $186
         

10.0 (128 Reviews)
Condo
Welcome to Derby City Loft!
  • Air Conditioner
  • Parking
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Amazing Luxury Urban Loft! West Main Street - Private Deck - Riverfront Views! From US $1,209
         

10.0 (118 Reviews)
Apartment
Amazing Luxury Urban Loft! West Main Street - Private Deck - Riverfront Views!
  • Air Conditioner
  • Parking
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Historic Flat - 2 minutes from Cincinnati From US $217
         

10.0 (66 Reviews)
Apartment
Historic Flat - 2 minutes from Cincinnati
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Kentucky Vacation Rentals and Airbnb Places to Stay Under $200

Over 6773+ Kentucky Vacation Rentals and Airbnb Places to Stay Under $200
See why everyone loves it here! 1.5 miles to Ark. From US $163
         

9.8 (197 Reviews)
House
See why everyone loves it here! 1.5 miles to Ark.
  • Air Conditioner
  • Parking
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Fairfield Farm Cottage From US $195
         

9.8 (9 Reviews)
House
Fairfield Farm Cottage
  • Air Conditioner
  • Parking
  • Balcony/Terrace

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Homestay on Main by Twin Lakes Creamery From US $115
         

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8.8 (45 Reviews)
Bed & Breakfast
Homestay on Main by Twin Lakes Creamery
  • Air Conditioner
  • Parking
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NEWPORT INN #5 - NO CLEANING FEES! FREE PARKING! WALK TO GAMES AND CONCERTS! From US $140
         

10.0 (154 Reviews)
Apartment
NEWPORT INN #5 - NO CLEANING FEES! FREE PARKING! WALK TO GAMES AND CONCERTS!
  • Air Conditioner
  • Parking
  • TV

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LAKE CUMBERLAND, ROMANTIC HOT TUB, FENCED YARD, RELAXATION, 100 meg WIFI From US $168
         

10.0 (273 Reviews)
Cottage
LAKE CUMBERLAND, ROMANTIC HOT TUB, FENCED YARD, RELAXATION, 100 meg WIFI
  • Air Conditioner
  • Parking
  • Pet Friendly

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Welcome to your home away from home at my Bardstown’s Sweet Retreat! From US $194
         

9.8 (83 Reviews)
House
Welcome to your home away from home at my Bardstown’s Sweet Retreat!
  • Air Conditioner
  • Parking
  • TV

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HOT TUB COTTAGE near Cave Run Lake, Kentucky, Red River Gorge,Morehead Kentucky From US $165
         

9.8 (61 Reviews)
Cottage
HOT TUB COTTAGE near Cave Run Lake, Kentucky, Red River Gorge,Morehead Kentucky
  • Air Conditioner
  • Parking
  • TV

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The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country. From US $164
         

10.0 (121 Reviews)
Cabin
The Cozy Cabin 2 Bedrooms 1 Bath is the perfect romantic getaway in the country.
  • Air Conditioner
  • Parking
  • TV

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Instantly Bookable Vacation Homes in Kentucky

Over 9156+ Instantly Bookable Vacation Homes in or Near Kentucky
Cottage At Brianza Gardens And Winery From US $303
         

10.0 (85 Reviews)
House
Cottage At Brianza Gardens And Winery
  • Air Conditioner
  • Parking
  • TV

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Carriage House, 7 minutes from downtown Louisville From US $239
         

10.0 (47 Reviews)
House
Carriage House, 7 minutes from downtown Louisville
  • Air Conditioner
  • Parking
  • TV

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Robin's Nest luxury cabin, Red River Gorge From US $321
         

9.8 (157 Reviews)
House
Robin's Nest luxury cabin, Red River Gorge
  • Air Conditioner
  • Parking
  • TV

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3 Bedroom Downtown Townhouse, Close to All! From US $207
         

9.4 (64 Reviews)
House
3 Bedroom Downtown Townhouse, Close to All!
  • Air Conditioner
  • Parking
  • TV

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The River's Edge Oasis.Relax & unwind.Casual luxury close to downtown Lville From US $334
         

10.0 (203 Reviews)
House
The River's Edge Oasis.Relax & unwind.Casual luxury close to downtown Lville
  • Air Conditioner
  • Parking
  • TV

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Woodland secluded cabin on 7 acres, with private dock and kayaks From US $389
         

9.6 (102 Reviews)
Cabin
Woodland secluded cabin on 7 acres, with private dock and kayaks
  • Air Conditioner
  • Parking
  • Designated Smoking Area

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Private Cottage at Lake Cumberland Resort- a gated lakefront Community From US $502
         

9.4 (133 Reviews)
Cabin
Private Cottage at Lake Cumberland Resort- a gated lakefront Community
  • Air Conditioner
  • Parking
  • Pet Friendly

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3BR 1.5BA w/King Bed/Hot Tub in Heart of RRG! From US $556
         

9.0 (99 Reviews)
Cabin
3BR 1.5BA w/King Bed/Hot Tub in Heart of RRG!
  • Air Conditioner
  • Pet Friendly
  • TV

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About Kentucky Vacation Rentals

With more than 15280 Kentucky vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Bigislandhawaiirental and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Kentucky.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Bigislandhawaiirental Kentucky, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Kentucky. Places to stay near Kentucky are 892.42 ft² on average, with prices averaging US $344 a night.

Bigislandhawaiirental makes it easy and safe to find and compare vacation rentals in Kentucky with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Kentucky

Type Count
Vacation Homes 7597
Holiday Apartments 2433
Cabin Rentals 1978
Hotels 1655
Cottages 459
B&B 155
Others 128
Villas 46
Resorts 41
Ski Chalet Rentals 35

Use these Quick Filters to Find a Vacation Rental in Kentucky

★ Pro Tip: Bigislandhawaiirental makes it easy to compare the best listings on Bigislandhawaiirental homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Bigislandhawaiirental homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Kentucky.

Weather in Kentucky

View the weather forecast for Kentucky before booking your Kentucky Vacation Rentals to confirm your best time to go.

December - February
High 59°F       Low 28°F
March - May
High 78°F       Low 40°F
June - August
High 89°F       Low 66°F
September - November
High 81°F       Low 40°F

Top Attractions Around Kentucky, US

Bigislandhawaiirental offers a large selection of top attractions around Kentucky. Research things to do on your vacation before you visit Kentucky.


Ark Encounter Newport Aquarium Mammoth Cave National Park Kentucky Exposition Center Creation Museum Rupp Arena University of Kentucky University of Louisville Kentucky Horse Park Churchill Downs KFC Yum Center Red River Gorge Fourth Street Live! Louisville Slugger Museum Newport on the Levee National Corvette Museum Fort Campbell Kentucky International Convention Center Louisville Palace Keeneland Racing Course Louisville Zoo Kentucky Lake Kentucky Kingdom Fayette Mall Cumberland Falls Louisville Mega Cavern Freedom Hall Murray State University Waverly Hills Sanatorium Kroger Field

Other Places to Stay Near Kentucky, US


Louisville 2,159 Properties Jefferson County 1,581 Properties Lebanon 1,324 Properties Marion County 1,300 Properties Lexington 1,274 Properties Fayette County 593 Properties Paducah 507 Properties Downtown 480 Properties Lake Barkley 423 Properties Downtown Louisville 421 Properties Wolfe County 408 Properties Northside District 407 Properties

Complexes around Kentucky, US


Summer Downtown Louisville 32 Properties Elizabethtown Inn 29 Properties Ark 33 Properties Inn Lexington 9 Properties Cozysuites Sky 18 Properties Inn 5 Properties Hopkinsville 15 Properties Cave Run 11 Properties Frontdesk 7 Properties Somerset 10 Properties Comfort Keeneland 3 Properties Downtown Lexington Rupp Arena Alltech 3 Properties The Bellwether Hotel 7 Properties Covington 6 Properties Boutique Hotel Henderson 7 Properties
See More Complexes

Kentucky Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Kentucky?

There are a lot of options in Kentucky. If you plan on staying in the Kentucky area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Kentucky:

How many vacation rentals are available in Kentucky?

Currently, the total number of properties listed in 2026 is over 15280 in the Kentucky area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Kentucky.