Vacation rentals in Monticello

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Top-rated vacation rentals in Monticello

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Tiny home in Monticello

4.97 out of 5 average rating, 160 reviews

Adorable Tiny LakeView Cottage with kayaks!

Totally remodeled inside and out! We welcome your fur babies!! Adorable tiny house with a deck & bonfire pit overlooking a spectacular view of Otter Creek on Lake Cumberland. It is located in Monticello, Ky in a rural part of the area. It’s about 12 minutes to town. There is very close (driving distance) swimming access, kayaking, boating, boat ramps, fishing & marinas. Plus, your likely to see lots of wildlife. I have kayaks available for a small daily fee to rent. Pets allowed! $50/$75fee.

Aug 10 – 17

R2,836 ZAR per night
Guest favorite

Home in Monticello

4.91 out of 5 average rating, 124 reviews

Bluegrass Gables: Lake Cumberland Cottage

Relax in the forest is this amazing 4bd/2.5ba cottage. Only minutes to the Ramsey Point boat ramp, this is your base for your Lake Cumberland vacation. Bring your boat; ample parking onsite. Don't have a boat? No problem, Beaver Creek and Conley Bottom marinas are close by. House features modern amenities and a fully stocked kitchen. Enjoy the fireplace indoors or the firepit outdoors. Forest views and fresh air galore await you, especially from the hot tub! Absolutely no smoking inside or out.

Sep 9 – 16

R5,505 ZAR per night
Guest favorite

Cottage in Monticello

4.91 out of 5 average rating, 97 reviews

Clean and Cozy. Only 175 yards from the water.

Cabin House is located at beautiful Lake Cumberland near Monticello, KY. It is located approximately 175 yards from Old Fall Creek boat ramp. This is a Free boat ramp. No dock. If you should need to rent a boat, we are located close to the resorts at Conley Bottom and Beaver Creek. The cabin is known for being clean and comfortable. It is nestled among the trees next to land overseen by the Army Corp of Engineers. The area is always beautiful no matter what season. Come and Enjoy!!

Jun 2 – 9

R1,972 ZAR per night

Popular amenities for Monticello vacation rentals

Stay near Monticello's top sights

Black Stallion Steak House11 locals recommend
El Cazador7 locals recommend
Pizza Hut7 locals recommend

Other great vacation rentals in Monticello

Guest favorite

Dome in Monticello

5.0 out of 5 average rating, 24 reviews

Dome + HotTub + Escape + Lake

Apr 6 – 13

R3,915 ZAR per night
Guest favorite

Cabin in Wayne County

4.93 out of 5 average rating, 44 reviews

Cozy cabin on private 18 acre farm near the lake.

Apr 17 – 24

R2,463 ZAR per night
Guest favorite

Tiny home in Nancy

4.89 out of 5 average rating, 53 reviews

Cabin near Wolf Creek Marina and public boat ramps

May 28 – Jun 4

R1,155 ZAR per night
Guest favorite

Home in Monticello

5.0 out of 5 average rating, 10 reviews

Lake Cumberland Beaver Creek Marina

Apr 25 – May 2

R2,524 ZAR per night
Guest favorite

Tiny home in Monticello

5.0 out of 5 average rating, 8 reviews

Stylish Skoolie Lake Cumberland

Jul 16 – 23

R1,928 ZAR per night
Guest favorite

Home in Monticello

5.0 out of 5 average rating, 31 reviews

Barndo Bliss-Luxe 2 King Suites, Fire Pit, Hot Tub

May 23 – 30

R9,704 ZAR per night
Guest favorite

Cabin in Stearns

5.0 out of 5 average rating, 29 reviews

John L. Wright Cabin

Oct 26 – Nov 2

R1,859 ZAR per night
Guest favorite

Home in Somerset

4.89 out of 5 average rating, 27 reviews

Buggs Lake Cabin

Nov 6 – 13

R1,888 ZAR per night
Guest favorite

Home in Somerset

4.86 out of 5 average rating, 28 reviews

Copper Roof Cottage

Dec 10 – 17

R1,476 ZAR per night
Superhost

Home in Somerset

5.0 out of 5 average rating, 3 reviews

Lake Cumberland Retreat #2 near Somerset and Ramps

May 20 – 27

R1,597 ZAR per night
Guest favorite

Home in Bronston

5.0 out of 5 average rating, 46 reviews

Lake Time's Yellow House near Conley & Burnside

Jun 11 – 18

R2,752 ZAR per night
Guest favorite

Home in Monticello

4.97 out of 5 average rating, 35 reviews

"Lake it Easy" at Conley Bottom & Lake Cumberland

Apr 24 – May 1

R4,138 ZAR per night

Destinations to explore

  1. Airbnb
  2. United States
  3. Kentucky
  4. Wayne County
  5. Monticello