Owner Direct Vacation
Rentals in Monticello

There are a lot of options in Monticello. If you plan on staying in the Monticello area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Monticello:

• Luxury Rustic Estate on Lake Freeman
• Waterfront Lake Shafer - Hot Tub + Fireplace
• Lake Freeman house w/boat dock. Minutes from Indiana Beach/Lake Shafer
• Lake front house with beautiful views and walking distance to Indiana Beach.
• Relaxing Cottage Nestled on Lake Freeman with Private Beachfront & Pool
• The Lake House Everyone Wants w/two decks, great amenities & optional Pontoon!
• Charming Cottage on Lake Shafer-optional Pontoon! Screened gazebo and swim deck!
• Gorgeous lake front cottage. Enjoy those summer nights on the lake
• Lakeside Paradise
• Tranquil Lake Cottage

There are 1 vacation rentals with private pools near Monticello. Top-rated homes that have access to a swimming pool include:

• Best Western Plus Brandywine Inn & Suites

If you are looking for a family-friendly vacation home in Monticello, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Monticello:

• Dave's Last Resort-House on the Lake home
• Family Friendly completely remodeled secluded vacation spot near Lake Shafer
• Alexanders Landing

Currently, the total number of properties listed in 2026 is over 184 in the Monticello area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Monticello.