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Search and Rent Monticello Condos

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Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Condo Rentals in Monticello

Woodson Bend 3 BR Condo, with Pool, AC, WiFi, Golf Course, Restaurant
Smart TV

Woodson Bend 3 BR Condo, with Pool, AC, WiFi, Golf Course, Restaurant

9.4 out of 10, Exceptional, (3)
"Very nice property. Was pleasantly surprised that the unit was more comfortable than what the photos showed. "
Woodson Bend 3 BR Condo, with Pool, AC, WiFi, Golf Course, Restaurant
Bird House on 7th Fairway Updated Lake Cumberland Condo - Woodson Bend Resort
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and ample dining space.

Bird House on 7th Fairway Updated Lake Cumberland Condo - Woodson Bend Resort

9.4 out of 10, Exceptional, (11)
"My family enjoyed our stay at Woodson Bend."
Bird House on 7th Fairway Updated Lake Cumberland Condo - Woodson Bend Resort
Woodson Bend Condo. Golf, Pool, Restaurant, Entertainment & More! Near Burnside.
Relax by the pool surrounded by lounge chairs and umbrellas, with a lifeguard stand nearby for added safety.

Woodson Bend Condo. Golf, Pool, Restaurant, Entertainment & More! Near Burnside.

8.0 out of 10, Very Good, (4)
"Nice location. All the supplies we needed were there. Very clean. A welcoming host. We really enjoyed our stay. "
Woodson Bend Condo. Golf, Pool, Restaurant, Entertainment & More! Near Burnside.
Lovely "Treehouse" 2-Bedroom Condo inside Lake Cumberland State Park
Relax on the deck with a view of the lush forest, featuring a wooden panel wall and carpeted floor.

Lovely "Treehouse" 2-Bedroom Condo inside Lake Cumberland State Park

4.0 star property
9.8 out of 10, Exceptional, (64)
"We enjoyed the condo, it was clean and area was perfect for our needs. "
Lovely "Treehouse" 2-Bedroom Condo inside Lake Cumberland State Park
Woodson Bend Resort~Lake Cumberland 27-1 Life Way 3BR, 3BA Condo
Stunning building with a central staircase and evenly spaced windows, offering a beautiful view from the upper level balcony.

Woodson Bend Resort~Lake Cumberland 27-1 Life Way 3BR, 3BA Condo

9.8 out of 10, Exceptional, (26)
"Place is great! Highly recommend!!!"
Woodson Bend Resort~Lake Cumberland 27-1 Life Way 3BR, 3BA Condo
14-2 Woodson Bend Tree Top Retreat
Relax in this serene space with a large table and six chairs, a ceiling fan, and a window offering a view of the surrounding trees and water.

14-2 Woodson Bend Tree Top Retreat

9.8 out of 10, Exceptional, (10)
"Condo was perfect for our weekend getaway. We had everything we needed to cook. Furniture and beds were nice. Owner was very responsive. Will stay here again!"
14-2 Woodson Bend Tree Top Retreat
Woodson Bend-Golf, Pool Restaurant& More-Near Burnside W/Lake View - First Floor
Relax on the covered porch with a view of the surrounding woods, featuring a table and two chairs.

Woodson Bend-Golf, Pool Restaurant& More-Near Burnside W/Lake View - First Floor

10.0 out of 10, Exceptional, (23)
"The condo was in a great location and was super nice for our family weekend to the lake!"
Woodson Bend-Golf, Pool Restaurant& More-Near Burnside W/Lake View - First Floor
NEW Cozy Condo I-4 @ Beautiful Lake Cumberland - perfect family getaway!
Outdoor dining

NEW Cozy Condo I-4 @ Beautiful Lake Cumberland - perfect family getaway!

10.0 out of 10, Exceptional, (4)
"The beds were comfy, the towels were so soft, the kitchen had what you needed! We were there to enjoy the lake and this was a perfect place to stay!"
NEW Cozy Condo I-4 @ Beautiful Lake Cumberland - perfect family getaway!
Lake Cumberland Resort Condo w/ Direct Lake Access
Sit on a rustic stone bench surrounded by a serene river and wooded area.

Lake Cumberland Resort Condo w/ Direct Lake Access

9.6 out of 10, Exceptional, (28)
"Great place, kids loved running around. Nice and relaxing after a day on the boat."
Lake Cumberland Resort Condo w/ Direct Lake Access
NEW Beautiful Condo I-3 Next to Lake Cumberland
Residential townhouses with pitched roofs and brick exteriors set amidst lush greenery.

NEW Beautiful Condo I-3 Next to Lake Cumberland

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great location! Kids love the pool"
$269 nightly
The price is $297
Aug 8 - Aug 9
Total includes taxes and fees
NEW Beautiful Condo I-3 Next to Lake Cumberland
Welcome to Lakeside Oasis – A Lakeside Getaway
Residents enjoy a serene riverside setting with a pool, tennis court, and lush greenery.

Welcome to Lakeside Oasis – A Lakeside Getaway

10.0 out of 10, Exceptional, (1)
"We were very pleased with our apartment. Beds were comfortable, bathrooms were clean, furniture was in excellent condition. The location is a very short walk to a beautiful beach. We would be very happy to stay again!"
Welcome to Lakeside Oasis – A Lakeside Getaway
Lakefront Condo at Woodson Bend Resort on Lake Cumberland
Relax by the pool with comfortable lounge chairs and a lifeguard on duty.

Lakefront Condo at Woodson Bend Resort on Lake Cumberland

9.8 out of 10, Exceptional, (7)
"Our family had a great weekend at the condo. It was a beautiful place with everything we needed."
Lakefront Condo at Woodson Bend Resort on Lake Cumberland
🍎APPLE VALLEY RESORT🛟Lake Cumberland Condo closest to Wolf Creek Dam & Park!⚓️
Guests can enjoy water activities amidst a serene natural setting with rocky outcrops and lush greenery.

🍎APPLE VALLEY RESORT🛟Lake Cumberland Condo closest to Wolf Creek Dam & Park!⚓️

3.5 star property
9.8 out of 10, Exceptional, (153)
"We loved Apple Sally’s condo! It was very clean, close to the lake, and had everything we needed for a perfect stay. Will definitely stay here again!"
🍎APPLE VALLEY RESORT🛟Lake Cumberland Condo closest to Wolf Creek Dam & Park!⚓️
Cozy Lake Cumberland Condo
Enjoy serene lakeside views and access to a variety of boats for a relaxing day on the water.

Cozy Lake Cumberland Condo

9.6 out of 10, Exceptional, (15)
"A cozy, clean and great property!"
Cozy Lake Cumberland Condo
Lake Condo by Pool & Courts - Perfect for Relaxation & Play!
Enjoy cooking in this fully equipped kitchen with a microwave, oven, and dishwasher.

Lake Condo by Pool & Courts - Perfect for Relaxation & Play!

Lake Condo by Pool & Courts - Perfect for Relaxation & Play!
Welcome to Seventh Heaven – The Perfect Getaway
Relax by the pool surrounded by lounge chairs and umbrellas.

Welcome to Seventh Heaven – The Perfect Getaway

Welcome to Seventh Heaven – The Perfect Getaway
Lake Cumberland Cozy 1 Bedroom 7-3 Woodson Bend Resort Condo Bronston Ky
Welcome to Woodson Bend Resort, set amidst lush greenery and a stone wall.

Lake Cumberland Cozy 1 Bedroom 7-3 Woodson Bend Resort Condo Bronston Ky

10.0 out of 10, Exceptional, (3)
"Tony was a terrific host. We had everything we needed. Great location next to the pool. We would definitely stay here again!"
Lake Cumberland Cozy 1 Bedroom 7-3 Woodson Bend Resort Condo Bronston Ky
Welcome to Green Lite Lakeview - Fresh Escape
Enjoy cooking in this well-equipped kitchen with stainless steel appliances, white cabinetry, and ample workspace.

Welcome to Green Lite Lakeview - Fresh Escape

Welcome to Green Lite Lakeview - Fresh Escape
Welcome to Bigelow’s Water View Bungalow – Your Lake Retreat
Enjoy a room with a high ceiling, ceiling fan, and sliding glass door leading to an outdoor dining area.

Welcome to Bigelow’s Water View Bungalow – Your Lake Retreat

9.8 out of 10, Exceptional, (10)
"We had a wonderful time - this is a beautiful and spacious condo with a great view!"
Welcome to Bigelow’s Water View Bungalow – Your Lake Retreat
Remodeled Lakefront Woodson Bend Condo- 92-2 Eagle Drive
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and oven, along with a sink and ample countertop space.

Remodeled Lakefront Woodson Bend Condo- 92-2 Eagle Drive

9.8 out of 10, Exceptional, (21)
"This is a great place to stay for a trip to Cumberland. Everything was as described. We would definitely stay again!"
Remodeled Lakefront Woodson Bend Condo- 92-2 Eagle Drive
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Monticello Hotel Reviews

Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!

Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!

10/10 Excellent
"We had a wonderful stay at this lake house in Monticello, KY on Lake Cumberland! The house was spotless and decorated so adorably—it really felt like a cozy retreat. The beds were super comfortable, and we all slept great. One of the highlights was the stunning lake view, which we enjoyed every morning and evening.The welcome kit was such a thoughtful touch and made us feel right at home from the moment we arrived. The game room was a huge hit with both the kids and the adults—we spent hours playing and laughing together.This place has everything you need for a relaxing and fun getaway. Highly recommend and would absolutely stay again!"
Elaine Y. 5-night trip
Posted 2 days ago
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!