Discover a selection of 217 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 kitchens. Prices start at $86 per night, and cabins and houses are popular options for a stay in Monticello. Either way, you'll find a rental for everyone's needs.
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, HomeAway 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 2020 property listings offer a large selection of 217 vacation rentals around Monticello. From 64 cabin rentals to 104 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a lake-view property in Monticello?

Imagine it. You and your posse, on your veranda, taking in incredible lake views with a refreshment in hand. Lakefront retreats are all about easygoing days and cozy stays. Vrbo has 72 vacation rentals near lakes ready to be booked. Open to more suggestions? Vrbo is teeming with other options to discover, including:

  • 45 lakefront vacation rentals.
  • 36 rural vacation rentals.
  • 35 water-view vacation rentals.

Can I rent a house in Monticello?

Our house vacation rentals are real accommodations for real travelers. Providing tons of space and privacy, they're perfect if you want to experience life like a local. There are 100 options currently available on Vrbo. Prices start at $75 a night. If that doesn't suit your posse's taste, we've got a number of other rental options to select from, such as:

  • Cabin: 59 vacation homes. Prices start from $89 per night.
  • Condo: 16 vacation homes. Prices start from $116 per night.
  • Hotel: 9 vacation homes. Prices start from $68 per night.

Can I stay in Monticello in a large group?

Getaways with your favorite people can be tons of fun, especially when you're staying under the same roof in an amazing new place! If you're traveling with a large group, Vrbo can help out. Cabin vacation homes are the leading choice here for large groups of travelers. Our database currently has 30 available. The rental options that are on offer for large groups in the area include:

  • If yours is a group of 6, we offer 58 vacation homes perfect for that size. Spend a night for as little as $89.
  • Need a rental property for 8 guests? We have 55 that will be perfect. You can get one for as little as $75 per night.
  • Looking for places for rent catering to 12 guests? You'll be thrilled to discover we have 26 that'll be ideal. You can secure one for as little as $225 per night.

You and the squad will be more than satisfied when you plan your Monticello getaway through us!

Where are the cheapest rentals in Monticello?

Vrbo is here to help you get together with the ones you love. Offering up a great selection of value-for-money rentals, you're sure to get an incredible hideout to suit everyone. Grabbing a rental in or around Apple Valley is an easy way to avoid burning a hole in your budget. We have 2 options and the average cost is $124 a night.