Discover a selection of 243 vacation rentals in Monticello that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $90 per night, and houses and cabins are popular options for a stay in Monticello. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Monticello
Destination guide

The remote city of Monticello awaits you

Enjoy the wineries and other features of Monticello. Well known for its lake, boating and fishing, this relaxing city won't disappoint. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.


Activities and attractions in and around Monticello

Are you hoping to find things to do while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Monticello has to offer. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Lake Cumberland Winery (10.2 mi / 16.4 km)
  • Lake Cumberland Golf Club (17 mi / 27.4 km)
  • Waitsboro Hills Golf Course (19.4 mi / 31.3 km)
  • SomerSplash (24.7 mi / 39.8 km)
  • Dale Hollow Lake State Resort Park Golf Course (27.3 mi / 43.9 km)
Natural features

Exploring the natural features in Monticello

Whether you're an adventurous traveler or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Monticello. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Lake Cumberland State Resort Park (14.7 mi / 23.7 km)
  • Mountain View Park (17.6 mi / 28.3 km)
  • General Burnside State Park (18 mi / 28.9 km)
  • Pulaski County Park (20.1 mi / 32.3 km)
  • Split Bow Arch Overlook (20.7 mi / 33.2 km)
  • Bandy Creek Visitors Center (22.6 mi / 36.3 km)

How many vacation rentals are available around Monticello?

Our 2021 property listings offer a large selection of 243 vacation rentals around Monticello. From 207 house rentals to 81 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.