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Monticello Holiday Rentals

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50 rentals in Monticello.
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Beautiful Vacation Home on Lake Cumberland, Monticello, KY, holiday rental in Monticello

Beautiful Vacation Home on Lake Cumberland, Monticello, KY

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Rustic Cabin - Year Round Lake View, holiday rental in Monticello

Rustic Cabin - Year Round Lake View

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Watch the sun set on the lake, two minute drive from Beaver Creek Marina!, holiday rental in Monticello

Watch the sun set on the lake, two minute drive from Beaver Creek Marina!

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Vacationers' Delight at Conley Bottom, holiday rental in Monticello

Vacationers' Delight at Conley Bottom

2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Beautiful Farmhouse near Lake Cumberland, holiday rental in Monticello

Beautiful Farmhouse near Lake Cumberland

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lake Cumberland Ky Summer Home In Monticello, holiday rental in Monticello

Lake Cumberland Ky Summer Home In Monticello

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Hidden Hilltop Hideaway, holiday rental in Monticello

Tentrr Signature Site - Hidden Hilltop Hideaway

1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps
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Look-Out Lodge on Lake Cumberland, holiday rental in Monticello

Look-Out Lodge on Lake Cumberland

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Lake House Hideaway #1, Only 2 miles from Jamestown Marina!!, holiday rental in Monticello

Lake House Hideaway #1, Only 2 miles from Jamestown Marina!!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Premium Condo by Lake Cumberland Park! Perfect Location! Newly Updated! Comfy!, holiday rental in Monticello

Premium Condo by Lake Cumberland Park! Perfect Location! Newly Updated! Comfy!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Lake House Hideaway #2-Only 1 Mile above Jamestown Marina!, holiday rental in Monticello

NEW! Lake House Hideaway #2-Only 1 Mile above Jamestown Marina!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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3 Bdrm Lake House Getaway - Three Minutes To Launch!, holiday rental in Monticello

3 Bdrm Lake House Getaway - Three Minutes To Launch!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Jamestown Marina - Boating, fishing, hiking & hunting on Lake Cumberland, holiday rental in Monticello

Jamestown Marina - Boating, fishing, hiking & hunting on Lake Cumberland

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Lakefront Home-Walk to Ramp and Pool, holiday rental in Monticello

Beautiful Lakefront Home-Walk to Ramp and Pool

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Lake Front Home with community boat ramp.Private, yet close to marinas and town, holiday rental in Monticello

Lake Front Home with community boat ramp.Private, yet close to marinas and town

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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3 BR/2 BA Luxury Cabin -Close To The Lake!, holiday rental in Monticello

3 BR/2 BA Luxury Cabin -Close To The Lake!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Enjoy the winter season at Lake Cumberland, holiday rental in Monticello

Enjoy the winter season at Lake Cumberland

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Overlooks Jamestown Marina & State Dock, Lakeview House, 4Br/3Ba, Sleeps 10, holiday rental in Monticello

Overlooks Jamestown Marina & State Dock, Lakeview House, 4Br/3Ba, Sleeps 10

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Lake House Hideaway #3, Only 2 miles from Jamestown Marina, holiday rental in Monticello

Lake House Hideaway #3, Only 2 miles from Jamestown Marina

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lake Front Home Wonderful Views Secluded Yet Close to Somerset, holiday rental in Monticello

Lake Front Home Wonderful Views Secluded Yet Close to Somerset

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Large Lake House 5 min from Jamestown Marina Ping Pong/Foosball table, Sleeps 10, holiday rental in Monticello

Large Lake House 5 min from Jamestown Marina Ping Pong/Foosball table, Sleeps 10

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Lake Cumberland Cabin with lake view, holiday rental in Monticello

Beautiful Lake Cumberland Cabin with lake view

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Loft Cabin with Hot Tub * LakePointe Resort - no cleaning fees!, holiday rental in Monticello

Loft Cabin with Hot Tub * LakePointe Resort - no cleaning fees!

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Americana Jacuzzi Lake View Cabin 2  3/4 mile to marina- NO CLEANING FEE!, holiday rental in Monticello

Americana Jacuzzi Lake View Cabin 2 3/4 mile to marina- NO CLEANING FEE!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Gated Community Home with Spectacular Lake View, holiday rental in Monticello

Gated Community Home with Spectacular Lake View

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Lake Cumberland/Conley Bottom area-Log Cabin Rental, Private, Lake Access .25 Mi, holiday rental in Monticello

Lake Cumberland/Conley Bottom area-Log Cabin Rental, Private, Lake Access .25 Mi

2 bedrooms
1 bathroom
Sleeps 9
Match: Sleeps
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Americana Hot Tub Cabin * LakePointe Resort - no cleaning fees!, holiday rental in Monticello

Americana Hot Tub Cabin * LakePointe Resort - no cleaning fees!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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'No Wake Zone' is  Lakefront and close to the boat  ramp, holiday rental in Monticello

'No Wake Zone' is Lakefront and close to the boat ramp

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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3 Bedroom Lake View Family Cabin  3/4 mile to marina! NO CLEANING FEE, holiday rental in Monticello

3 Bedroom Lake View Family Cabin 3/4 mile to marina! NO CLEANING FEE

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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2 Bedroom Family Cottage#3 Cumberland Marina-NO CLEANING FEE!, holiday rental in Monticello

2 Bedroom Family Cottage#3 Cumberland Marina-NO CLEANING FEE!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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As close to the Lake as you can get!!! Lake Cumberland Marina/ Alligator Dock 2, holiday rental in Monticello

As close to the Lake as you can get!!! Lake Cumberland Marina/ Alligator Dock 2

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Award Winning Hot Tub Cabin * LakePointe Resort - no cleaning fees!, holiday rental in Monticello

Award Winning Hot Tub Cabin * LakePointe Resort - no cleaning fees!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Don't Miss This Beautiful Custom Built Lake House, holiday rental in Monticello

Don't Miss This Beautiful Custom Built Lake House

5 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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Ultimate Getaway on Lake Cumberland, Great Location and Rare Private Dock & Ramp, holiday rental in Monticello

Ultimate Getaway on Lake Cumberland, Great Location and Rare Private Dock & Ramp

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Nancy Kentucky 1800s log cabin, holiday rental in Monticello

Nancy Kentucky 1800s log cabin

1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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'Beary' Cute Hot Tub Cabin * LakePointe Resort - no cleaning fees!, holiday rental in Monticello

'Beary' Cute Hot Tub Cabin * LakePointe Resort - no cleaning fees!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Visit a Piece of Paradise!, holiday rental in Monticello

Visit a Piece of Paradise!

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Jamestown Marina & State Dock Location, 4 BR/2BA, Sleeps 12, holiday rental in Monticello

Jamestown Marina & State Dock Location, 4 BR/2BA, Sleeps 12

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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The Hot Tub Cabin at the Barn * LakePointe Resort - no cleaning fees!, holiday rental in Monticello

The Hot Tub Cabin at the Barn * LakePointe Resort - no cleaning fees!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lake Time Cottage, 3 Bedroom 2 Bath, <3 Mile from Jamestown, holiday rental in Monticello

Lake Time Cottage, 3 Bedroom 2 Bath, <3 Mile from Jamestown

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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LakePointe's 'Super Cabin' - No Cleaning Fees!, holiday rental in Monticello

LakePointe's 'Super Cabin' - No Cleaning Fees!

2 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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*************** Award Winning Cabin * LakePointe - no cleaning fees!, holiday rental in Monticello

*************** Award Winning Cabin * LakePointe - no cleaning fees!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cabin in the Woods * LakePointe Resort - no cleaning fees! Cabin B, holiday rental in Monticello

Cabin in the Woods * LakePointe Resort - no cleaning fees! Cabin B

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Hornets Nest by the water, holiday rental in Monticello

The Hornets Nest by the water

3 bedrooms
1 bathroom
Sleeps 9
Match: Sleeps
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*************** Award Winning Cabin * LakePointe - no cleaning fees!, holiday rental in Monticello

*************** Award Winning Cabin * LakePointe - no cleaning fees!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Monticello Home w/ Multi-Level Deck on 2+ Acres!, holiday rental in Monticello

Monticello Home w/ Multi-Level Deck on 2+ Acres!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lake Cumberland Home: ½ Mi to Beaver Creek Marina!, holiday rental in Monticello

Lake Cumberland Home: ½ Mi to Beaver Creek Marina!

5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Lakefront Home w/ Multi-Level Deck, Near Somerset!, holiday rental in Monticello

Lakefront Home w/ Multi-Level Deck, Near Somerset!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Lake Cumberland Family Condo w/ Pool & Tennis, holiday rental in Monticello

NEW! Lake Cumberland Family Condo w/ Pool & Tennis

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Lake Cumberland Home w/ Deck + Water Access!, holiday rental in Monticello

NEW! Lake Cumberland Home w/ Deck + Water Access!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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