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Pleasureville Vacation Rentals

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Bedrooms

Bathrooms

Amenities

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Distance from

5 mi
49 rentals in Pleasureville.
Beautiful Cottage in Gorgeous Rural Setting, vacation rental in Pleasureville
Beautiful Cottage in Gorgeous Rural Setting, vacation rental in Pleasureville
Beautiful Cottage in Gorgeous Rural Setting, vacation rental in Pleasureville

Beautiful Cottage in Gorgeous Rural Setting

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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The following properties within 20 miles of Pleasureville match all your filters:
Bourbon Trail, Ark Encounter, Family Gatherings, vacation rental in Pleasureville
Bourbon Trail, Ark Encounter, Family Gatherings, vacation rental in Pleasureville
Bourbon Trail, Ark Encounter, Family Gatherings, vacation rental in Pleasureville

Bourbon Trail, Ark Encounter, Family Gatherings

Rental Home
4 bedrooms
3 bathrooms
Sleeps 29
Match: Sleeps
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Historic home freshly renovated on the Bourbon Trail, vacation rental in Pleasureville
Historic home freshly renovated on the Bourbon Trail, vacation rental in Pleasureville
Historic home freshly renovated on the Bourbon Trail, vacation rental in Pleasureville

Historic home freshly renovated on the Bourbon Trail

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Upscale Kentucky Bourbon Trail & Close to Louisville, vacation rental in Pleasureville
Upscale Kentucky Bourbon Trail & Close to Louisville, vacation rental in Pleasureville
Upscale Kentucky Bourbon Trail & Close to Louisville, vacation rental in Pleasureville

Upscale Kentucky Bourbon Trail & Close to Louisville

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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KY Bourbon Trail Home, King Bed, FirePit, Near Louisville, vacation rental in Pleasureville
KY Bourbon Trail Home, King Bed, FirePit, Near Louisville, vacation rental in Pleasureville
KY Bourbon Trail Home, King Bed, FirePit, Near Louisville, vacation rental in Pleasureville

KY Bourbon Trail Home, King Bed, FirePit, Near Louisville

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Your Kentucky Home Away From Home, vacation rental in Pleasureville
Your Kentucky Home Away From Home, vacation rental in Pleasureville
Your Kentucky Home Away From Home, vacation rental in Pleasureville

Your Kentucky Home Away From Home

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful restored Victorian farmhouse, vacation rental in Pleasureville
Beautiful restored Victorian farmhouse, vacation rental in Pleasureville
Beautiful restored Victorian farmhouse, vacation rental in Pleasureville

Beautiful restored Victorian farmhouse

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Unique Downtown Studio with an Industrial Vibe, vacation rental in Pleasureville
Unique Downtown Studio with an Industrial Vibe, vacation rental in Pleasureville
Unique Downtown Studio with an Industrial Vibe, vacation rental in Pleasureville

Unique Downtown Studio with an Industrial Vibe

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Bourbon Trail River House, vacation rental in Pleasureville
Bourbon Trail River House, vacation rental in Pleasureville
Bourbon Trail River House, vacation rental in Pleasureville

Bourbon Trail River House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Downtown Main Street Suite w/ Hi-Speed Wifi, vacation rental in Pleasureville
Downtown Main Street Suite w/ Hi-Speed Wifi, vacation rental in Pleasureville
Downtown Main Street Suite w/ Hi-Speed Wifi, vacation rental in Pleasureville

Downtown Main Street Suite w/ Hi-Speed Wifi

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Private Home Gallery | Louisville| New Listing | Hot Tub | Modern | Bourbon, vacation rental in Pleasureville
Private Home Gallery | Louisville| New Listing | Hot Tub | Modern | Bourbon, vacation rental in Pleasureville
Private Home Gallery | Louisville| New Listing | Hot Tub | Modern | Bourbon, vacation rental in Pleasureville

Private Home Gallery | Louisville| New Listing | Hot Tub | Modern | Bourbon

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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New Modern Townhome, sleeps 6! Mod Farm 1217, vacation rental in Pleasureville
New Modern Townhome, sleeps 6! Mod Farm 1217, vacation rental in Pleasureville
New Modern Townhome, sleeps 6! Mod Farm 1217, vacation rental in Pleasureville

New Modern Townhome, sleeps 6! Mod Farm 1217

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Hillside Hideout With Scenic Bluegrass Setting!, vacation rental in Pleasureville
Hillside Hideout With Scenic Bluegrass Setting!, vacation rental in Pleasureville
Hillside Hideout With Scenic Bluegrass Setting!, vacation rental in Pleasureville

Hillside Hideout With Scenic Bluegrass Setting!

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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NEW - Luxury farmhouse on Bourbon Trail with hot tub - 4 mi to Bulleit, vacation rental in Pleasureville
NEW - Luxury farmhouse on Bourbon Trail with hot tub - 4 mi to Bulleit, vacation rental in Pleasureville
NEW - Luxury farmhouse on Bourbon Trail with hot tub - 4 mi to Bulleit, vacation rental in Pleasureville

NEW - Luxury farmhouse on Bourbon Trail with hot tub - 4 mi to Bulleit

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Upscale Kentucky Bourbon Trail & Close to Louisville, vacation rental in Pleasureville
Upscale Kentucky Bourbon Trail & Close to Louisville, vacation rental in Pleasureville
Upscale Kentucky Bourbon Trail & Close to Louisville, vacation rental in Pleasureville

Upscale Kentucky Bourbon Trail & Close to Louisville

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Le Coop Ultra Luxury 2 bed Urban Loft on Bourbon Trail.  Downtown Shelbyville KY, vacation rental in Pleasureville
Le Coop Ultra Luxury 2 bed Urban Loft on Bourbon Trail.  Downtown Shelbyville KY, vacation rental in Pleasureville
Le Coop Ultra Luxury 2 bed Urban Loft on Bourbon Trail.  Downtown Shelbyville KY, vacation rental in Pleasureville

Le Coop Ultra Luxury 2 bed Urban Loft on Bourbon Trail. Downtown Shelbyville KY

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Creek Front Camping - Secluded, Scenic and Comfortable, vacation rental in Pleasureville
Creek Front Camping - Secluded, Scenic and Comfortable, vacation rental in Pleasureville
Creek Front Camping - Secluded, Scenic and Comfortable, vacation rental in Pleasureville

Creek Front Camping - Secluded, Scenic and Comfortable

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Secluded getaway for 2, vacation rental in Pleasureville
Secluded getaway for 2, vacation rental in Pleasureville
Secluded getaway for 2, vacation rental in Pleasureville

Secluded getaway for 2

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Upscale Kentucky Bourbon Trail & Close to Louisville, vacation rental in Pleasureville
Upscale Kentucky Bourbon Trail & Close to Louisville, vacation rental in Pleasureville
Upscale Kentucky Bourbon Trail & Close to Louisville, vacation rental in Pleasureville

Upscale Kentucky Bourbon Trail & Close to Louisville

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Horse farm on the Kentucky Bourbon Trail, vacation rental in Pleasureville
Horse farm on the Kentucky Bourbon Trail, vacation rental in Pleasureville
Horse farm on the Kentucky Bourbon Trail, vacation rental in Pleasureville

Horse farm on the Kentucky Bourbon Trail

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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SLEEPS 6! Loft w/1 Queen & 2 Doubles, Bar, 2 TVs, vacation rental in Pleasureville
SLEEPS 6! Loft w/1 Queen & 2 Doubles, Bar, 2 TVs, vacation rental in Pleasureville
SLEEPS 6! Loft w/1 Queen & 2 Doubles, Bar, 2 TVs, vacation rental in Pleasureville

SLEEPS 6! Loft w/1 Queen & 2 Doubles, Bar, 2 TVs

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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oasis 522!, vacation rental in Pleasureville
oasis 522!, vacation rental in Pleasureville
oasis 522!, vacation rental in Pleasureville

oasis 522!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Peaceful, Beautiful Views, 10 miles to State Capitol, vacation rental in Pleasureville
Peaceful, Beautiful Views, 10 miles to State Capitol, vacation rental in Pleasureville
Peaceful, Beautiful Views, 10 miles to State Capitol, vacation rental in Pleasureville

Peaceful, Beautiful Views, 10 miles to State Capitol

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Horses, Bourbon and More .... Shelbyville Condo, vacation rental in Pleasureville
Horses, Bourbon and More .... Shelbyville Condo, vacation rental in Pleasureville
Horses, Bourbon and More .... Shelbyville Condo, vacation rental in Pleasureville

Horses, Bourbon and More .... Shelbyville Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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New Modern Townhome, sleeps 6. Mod Farm 1219, vacation rental in Pleasureville
New Modern Townhome, sleeps 6. Mod Farm 1219, vacation rental in Pleasureville
New Modern Townhome, sleeps 6. Mod Farm 1219, vacation rental in Pleasureville

New Modern Townhome, sleeps 6. Mod Farm 1219

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Bagdad Bungalow on Bourbon Trail, vacation rental in Pleasureville
Bagdad Bungalow on Bourbon Trail, vacation rental in Pleasureville
Bagdad Bungalow on Bourbon Trail, vacation rental in Pleasureville

Bagdad Bungalow on Bourbon Trail

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Horse Farm in Kentucky Bourbon Country! Book a Farm Tour and Horse Experience!, vacation rental in Pleasureville
Horse Farm in Kentucky Bourbon Country! Book a Farm Tour and Horse Experience!, vacation rental in Pleasureville
Horse Farm in Kentucky Bourbon Country! Book a Farm Tour and Horse Experience!, vacation rental in Pleasureville

Horse Farm in Kentucky Bourbon Country! Book a Farm Tour and Horse Experience!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Two Bourbon Barrel Cabins, vacation rental in Pleasureville
Two Bourbon Barrel Cabins, vacation rental in Pleasureville
Two Bourbon Barrel Cabins, vacation rental in Pleasureville

Two Bourbon Barrel Cabins

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Lagrange Loft - Small Town USA - Bourbon Trail, vacation rental in Pleasureville
Lagrange Loft - Small Town USA - Bourbon Trail, vacation rental in Pleasureville
Lagrange Loft - Small Town USA - Bourbon Trail, vacation rental in Pleasureville

Lagrange Loft - Small Town USA - Bourbon Trail

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Heritage House 1900’s home part/close to the Bourbon Trail, vacation rental in Pleasureville
Heritage House 1900’s home part/close to the Bourbon Trail, vacation rental in Pleasureville
Heritage House 1900’s home part/close to the Bourbon Trail, vacation rental in Pleasureville

Heritage House 1900’s home part/close to the Bourbon Trail

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Farmhouse Hannah near Louisville, vacation rental in Pleasureville
Farmhouse Hannah near Louisville, vacation rental in Pleasureville
Farmhouse Hannah near Louisville, vacation rental in Pleasureville

Farmhouse Hannah near Louisville

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill, vacation rental in Pleasureville
Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill, vacation rental in Pleasureville
Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill, vacation rental in Pleasureville

Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Beautiful, Peaceful Lakefront home in ❤️ of Bourbon Country in Shelbyville, KY, vacation rental in Pleasureville
Beautiful, Peaceful Lakefront home in ❤️ of Bourbon Country in Shelbyville, KY, vacation rental in Pleasureville
Beautiful, Peaceful Lakefront home in ❤️ of Bourbon Country in Shelbyville, KY, vacation rental in Pleasureville

Beautiful, Peaceful Lakefront home in ❤️ of Bourbon Country in Shelbyville, KY

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Peaceful, lakefront house on Guist Creek Lake/ Shelbyville-Bourbon Trail, vacation rental in Pleasureville
Peaceful, lakefront house on Guist Creek Lake/ Shelbyville-Bourbon Trail, vacation rental in Pleasureville
Peaceful, lakefront house on Guist Creek Lake/ Shelbyville-Bourbon Trail, vacation rental in Pleasureville

Peaceful, lakefront house on Guist Creek Lake/ Shelbyville-Bourbon Trail

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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King Bed-Hot Tub-Arcade! Perfect for couples and families. Close to I-71., vacation rental in Pleasureville
King Bed-Hot Tub-Arcade! Perfect for couples and families. Close to I-71., vacation rental in Pleasureville
King Bed-Hot Tub-Arcade! Perfect for couples and families. Close to I-71., vacation rental in Pleasureville

King Bed-Hot Tub-Arcade! Perfect for couples and families. Close to I-71.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Rec Farm: Cabin | Rec Barn | HotTub | Fire Pit, vacation rental in Pleasureville
The Rec Farm: Cabin | Rec Barn | HotTub | Fire Pit, vacation rental in Pleasureville
The Rec Farm: Cabin | Rec Barn | HotTub | Fire Pit, vacation rental in Pleasureville

The Rec Farm: Cabin | Rec Barn | HotTub | Fire Pit

Rental Home
3 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
More info
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Charming 1900’s house close to downtown Shelbyville, vacation rental in Pleasureville
Charming 1900’s house close to downtown Shelbyville, vacation rental in Pleasureville
Charming 1900’s house close to downtown Shelbyville, vacation rental in Pleasureville

Charming 1900’s house close to downtown Shelbyville

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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Luxury Log Cabin 10 minutes from Frankfort, KY, vacation rental in Pleasureville
Luxury Log Cabin 10 minutes from Frankfort, KY, vacation rental in Pleasureville
Luxury Log Cabin 10 minutes from Frankfort, KY, vacation rental in Pleasureville

Luxury Log Cabin 10 minutes from Frankfort, KY

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Blue Wing Landing Inn -Secluded on 240 acres!, vacation rental in Pleasureville
Blue Wing Landing Inn -Secluded on 240 acres!, vacation rental in Pleasureville
Blue Wing Landing Inn -Secluded on 240 acres!, vacation rental in Pleasureville

Blue Wing Landing Inn -Secluded on 240 acres!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
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Affiliated with FlipKey
LIKE NEW! Sleeps 10+ Lakeside Farmhouse - 45 Acres, vacation rental in Pleasureville
LIKE NEW! Sleeps 10+ Lakeside Farmhouse - 45 Acres, vacation rental in Pleasureville
LIKE NEW! Sleeps 10+ Lakeside Farmhouse - 45 Acres, vacation rental in Pleasureville

LIKE NEW! Sleeps 10+ Lakeside Farmhouse - 45 Acres

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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LUKE BRYAN CONCERT-Mulberry Orchard 2 miles-�DERBY STAY, vacation rental in Pleasureville
LUKE BRYAN CONCERT-Mulberry Orchard 2 miles-�DERBY STAY, vacation rental in Pleasureville
LUKE BRYAN CONCERT-Mulberry Orchard 2 miles-�DERBY STAY, vacation rental in Pleasureville

LUKE BRYAN CONCERT-Mulberry Orchard 2 miles-�DERBY STAY

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Like New Cabin near Lexington & Louisville - Sleeps 16, vacation rental in Pleasureville
Like New Cabin near Lexington & Louisville - Sleeps 16, vacation rental in Pleasureville
Like New Cabin near Lexington & Louisville - Sleeps 16, vacation rental in Pleasureville

Like New Cabin near Lexington & Louisville - Sleeps 16

Rental Home
4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
More info
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Historical Blue Wing Landing Inn, near the Ark Encounter., vacation rental in Pleasureville
Historical Blue Wing Landing Inn, near the Ark Encounter., vacation rental in Pleasureville
Historical Blue Wing Landing Inn, near the Ark Encounter., vacation rental in Pleasureville

Historical Blue Wing Landing Inn, near the Ark Encounter.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
More info
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Bourbon Trail / Ark Encounter / Horse Racing: Cabin, Fishing, Hunting, & Firepit, vacation rental in Pleasureville
Bourbon Trail / Ark Encounter / Horse Racing: Cabin, Fishing, Hunting, & Firepit, vacation rental in Pleasureville
Bourbon Trail / Ark Encounter / Horse Racing: Cabin, Fishing, Hunting, & Firepit, vacation rental in Pleasureville

Bourbon Trail / Ark Encounter / Horse Racing: Cabin, Fishing, Hunting, & Firepit

Rental Home
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Bottled in Bond: Featured on HGTV, Heart of Bourbon Trail, Sleeps 10, vacation rental in Pleasureville
Bottled in Bond: Featured on HGTV, Heart of Bourbon Trail, Sleeps 10, vacation rental in Pleasureville
Bottled in Bond: Featured on HGTV, Heart of Bourbon Trail, Sleeps 10, vacation rental in Pleasureville

Bottled in Bond: Featured on HGTV, Heart of Bourbon Trail, Sleeps 10

Condo/Apartment
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Stone Spring Farm situated in the center of Kentucky's Bourbon Country, vacation rental in Pleasureville
Stone Spring Farm situated in the center of Kentucky's Bourbon Country, vacation rental in Pleasureville
Stone Spring Farm situated in the center of Kentucky's Bourbon Country, vacation rental in Pleasureville

Stone Spring Farm situated in the center of Kentucky's Bourbon Country

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Luxury lodge in the heart of the Bluegrass, vacation rental in Pleasureville
Luxury lodge in the heart of the Bluegrass, vacation rental in Pleasureville
Luxury lodge in the heart of the Bluegrass, vacation rental in Pleasureville

Luxury lodge in the heart of the Bluegrass

Rental Home
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
More info
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Mid-Century Modern Lake House, vacation rental in Pleasureville
Mid-Century Modern Lake House, vacation rental in Pleasureville
Mid-Century Modern Lake House, vacation rental in Pleasureville

Mid-Century Modern Lake House

Rental Home
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
More info
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⭐️NEW!  - Large & Small Groups | Sleeps up to 16 |6br's | 6 baths - 3,000 sqft., vacation rental in Pleasureville
⭐️NEW!  - Large & Small Groups | Sleeps up to 16 |6br's | 6 baths - 3,000 sqft., vacation rental in Pleasureville
⭐️NEW!  - Large & Small Groups | Sleeps up to 16 |6br's | 6 baths - 3,000 sqft., vacation rental in Pleasureville

⭐️NEW! - Large & Small Groups | Sleeps up to 16 |6br's | 6 baths - 3,000 sqft.

Rental Home
6 bedrooms
6 bathrooms
Sleeps 17
Match: Sleeps
More info
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Showing results 1-49 of 49
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