Monticello vacation rentals

We found 106 vacation rentals — enter your dates for availability

Select from 45 homes, 10 cottages, and other vacation rentals in Monticello to find one that's perfect for your trip. Vacation homes offer the best amenities for your stay with friends, family, or just your pet, like cable TV and a washer and dryer. At the end of the day, you'll be sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Monticello

Why visit Monticello

  • Outdoor Adventures: Monticello is perfect for outdoor enthusiasts, offering activities like hiking, fishing, and boating in its beautiful parks and marinas.
  • Scenic Views: Experience stunning landscapes and picturesque countryside, ideal for relaxing getaways and family outings.
  • Family-Friendly Atmosphere: Monticello provides a welcoming environment, making it suitable for families seeking fun and adventure together.
  • Diverse Accommodations: Choose from a variety of vacation rentals, including cozy cabins and spacious homes, tailored to your needs.
  • Nearby Attractions: Explore surrounding areas for even more outdoor activities and unique experiences.

Popular types of accommodation in Monticello

Planning a getaway to Monticello? The excitement begins with finding the perfect vacation rental. Discover a range of options, from houses to cozy cabins and charming cottages. Whether you need large bedrooms or full bathrooms, Monticello has ideal accommodations to suit your needs. Explore the best vacation rentals that promise comfort and convenience for your trip.

  • Houses: The top choice for visitors in Monticello, offering spacious and comfortable stays perfect for families or groups.
  • Cabins: A popular second option, these rustic retreats provide a cozy atmosphere for a nature-inspired getaway.
  • Cottages: Charming and quaint, cottages in Monticello are ideal for couples or small families seeking a peaceful escape.
  • Condos: A convenient fourth option, condos offer modern amenities and easy access to local attractions.
  • Chalets: These unique accommodations provide a blend of luxury and nature, making for an unforgettable stay in Monticello.**

Top attractions in and around Monticello

Monticello, Kentucky, is an ideal destination for outdoor enthusiasts and adventure seekers. With its beautiful marinas, parks, and national parks, visitors can enjoy a variety of eco-friendly experiences perfect for families. Whether you're exploring scenic views or engaging in outdoor activities, Monticello offers a memorable vacation filled with natural beauty and adventure.

  • Conley Bottom Marina: Located within Monticello, this marina offers thrilling outdoor adventures on Lake Cumberland, perfect for boating, fishing, and relaxing on the beach with family and friends.
  • Lake Cumberland State Resort Park: Just 13 miles from Monticello, this national park is renowned for its stunning scenery, adventurous hiking trails, and an abundance of outdoor activities, making it a nature lover's paradise.
  • Wayne County Hospital: Situated in Monticello, this medical center provides essential services with a focus on family care and community health, embodying a supportive and professional environment.

Things to do recommended for couples

Monticello offers charming experiences for couples. Enjoy a scenic boat ride on Lake Cumberland, explore the beautiful natural trails at the nearby Daniel Boone National Forest, or savor a romantic dinner at a local restaurant, making unforgettable memories together in this serene setting.

Things to do recommended for families

Families will appreciate the scenic beauty of Lake Cumberland, where you can enjoy boating, fishing, and swimming. Visit the Wayne County Historical Museum for a glimpse into local history, or explore the nearby Daniel Boone National Forest for hiking and picnicking adventures.

Things to do recommended for groups

Groups visiting Monticello can enjoy a guided tour of the historic sites, partake in fishing or boating on Lake Cumberland, and explore the scenic beauty of the Daniel Boone National Forest, offering hiking trails and picnic areas perfect for gathering and relaxation.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Monticello

When planning your trip—whether you're traveling with friends, family, pets, or seeking extended stays—be sure to prioritize your preferences with the right filters. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Monticello with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Monticello with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Monticello: For many families, a trip isn't truly complete without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties offer amenities like food bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Monticello: If you're searching for vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Monticello

Monticello, Kentucky, offers a delightful blend of outdoor adventures and scenic beauty, making it an ideal destination for families and those seeking a relaxing escape. Explore the surrounding countryside, where you can enjoy stunning views and a friendly atmosphere. Nearby areas provide additional opportunities for outdoor activities and business-friendly environments, ensuring a well-rounded travel experience. Whether you're looking for seclusion or family-friendly vibes, Monticello has something for everyone.

  • Lake Cumberland: Nestled 12 miles from Monticello, Lake Cumberland is a picturesque destination known for its stunning natural beauty and recreational opportunities. This expansive lake is perfect for outdoor enthusiasts seeking a romantic getaway or an adventure-filled family trip. Visitors can enjoy a variety of activities such as hiking along scenic trails, camping under the stars, or simply relaxing by the water. The area is home to the Lake Cumberland State Resort Park, where you can explore walking paths, scenic overlooks, and picnic areas, all while soaking in the breathtaking views of the lake.
  • Jamestown: Located 16 miles from Monticello, Jamestown is a charming city that offers a blend of outdoor recreation and scenic landscapes. Known for its welcoming atmosphere, Jamestown is ideal for couples and families alike. Outdoor activities abound, with well-maintained campgrounds and hiking trails that allow visitors to immerse themselves in nature. The nearby Lake Cumberland and national state parks provide ample opportunities for fishing, boating, and exploring the great outdoors, making it a perfect stop for those seeking adventure and tranquility.
  • Alpha: Just 10 miles away from Monticello, Alpha is a hidden gem that attracts visitors looking for an adventurous outdoor experience. This city is surrounded by stunning landscapes and is in close proximity to national parks and a marina. Alpha offers various recreational areas and a resort for those wishing to unwind and enjoy the natural beauty of the region. With its diverse outdoor activities, including hiking, boating, and exploring the nearby lakes, Alpha is an excellent choice for thrill-seekers and nature lovers alike.

Best time to go to Monticello

If you're planning a trip to Monticello, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.6°F (2.0°C)Light RainMostly CloudyAverageSlightly Low
February40.1°F (4.5°C)Light RainMostly CloudyAverageSlightly Low
March48.0°F (8.9°C)Light RainMostly CloudyAverageSlightly Low
April56.8°F (13.8°C)Light RainMostly SunnyAverageAverage
May65.8°F (18.8°C)Light RainMostly SunnyAverageAverage
June73.6°F (23.1°C)Light RainMostly SunnySlightly HighSlightly High
July76.3°F (24.6°C)Light RainMostly SunnySlightly HighSlightly High
August74.8°F (23.8°C)Light RainMostly SunnySlightly HighSlightly High
September69.4°F (20.8°C)Light RainMostly SunnyAverageAverage
October58.6°F (14.8°C)Light RainMostly SunnySlightly LowAverage
November47.5°F (8.6°C)Light RainMostly SunnySlightly LowAverage
December41.4°F (5.2°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is a breeze

Planning your next getaway? Being flexible with your travel dates can lead to great savings, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even more significant discounts. To discover a Vrbo property that meets your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options for your trip.

Save more with One Key

When you book a qualifying Vrbo for your group getaway, you'll receive OneKeyCash on the full amount of your reservation. Being the organizer truly has its benefits. By joining our One Key rewards program, you can unlock special member discounts and earn OneKeyCash on eligible stays. Sign up today and begin reaping the rewards.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board provides you with a convenient way to plan your travel. You can start new trips, pick up right where you left off, or review and organize your travel plans with ease. Any properties you've saved or booked in the past are now neatly categorized under Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The remote area of Monticello awaits your stay

Enjoy the wineries and other features of Monticello. This relaxing city is known for its lake, boating and fishing. If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Monticello

Do you want to find things to do while you're in town? Venture out of your vacation home and experience everything that makes Monticello a fun place to get away. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • SomerSplash (23.3 mi / 37.5 km)
  • Dale Hollow Lake State Resort Park Golf Course (27.4 mi / 44 km)
  • Lake Cumberland Winery (7.9 mi / 12.6 km)
  • Natural Arch Scenic Area (15.9 mi / 25.6 km)
  • The Links Resort Golf Course (14.7 mi / 23.7 km)

Exploring the natural features in Monticello

Whether you're an active traveler or just want to spend some time taking in the scenery, Monticello is a great spot to appreciate mother nature. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Cumberland Point Recreation Area (9.4 mi / 15.1 km)
  • Lake Cumberland State Resort Park (12.7 mi / 20.4 km)
  • Wolf Creek National Fish Hatchery (16.7 mi / 26.9 km)
  • Yahoo Falls (18.5 mi / 29.8 km)
  • Pickett State Park (19.1 mi / 30.7 km)
  • Twin Arches (27.1 mi / 43.6 km)

Frequently asked questions

What is the best area to stay in Monticello, Kentucky, United States of America when booking a vacation rental?
When considering a vacation rental in Monticello, Kentucky, the area near the picturesque Lake Cumberland is an excellent choice. This neighborhood offers a serene atmosphere with beautiful waterfront views and easy access to various recreational activities. Lake Cumberland is renowned for its boating, fishing, and swimming opportunities, making it a fantastic spot for water enthusiasts.

Additionally, staying close to the Monticello city center provides convenient access to local dining options and shops, allowing visitors to immerse themselves in the charming community vibe. Nearby, you'll find the historic Mill Springs Battlefield, which is a significant Civil War site that offers fascinating insights into the region's history.
How much does it cost to rent a vacation home in Monticello?
Prices for vacation rentals in Monticello vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Monticello to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Monticello vacation house rentals?
You can find great discounts on house rentals in Monticello on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Monticello?
In Monticello, vacation houses are the most common type of rental, with about 41 available throughout the area. These homes typically feature spacious layouts, multiple bedrooms, and amenities such as fully equipped kitchens and outdoor areas for relaxation, making them ideal for families or larger groups. In addition to vacation houses, there are around 10 cottages that offer a more quaint and cozy atmosphere, often situated near natural attractions. There are also several cabins and mobile homes, which provide unique and rustic experiences for travelers looking to immerse themselves in the area's scenic surroundings.
Are there any family house rentals in Monticello?
In Monticello, Kentucky, families will find a solid selection of vacation rentals, with around 47 options available. The area is known for its beautiful lakes and outdoor activities, making it an excellent spot for family gatherings. Many of these homes come with spacious living areas, fully equipped kitchens great for preparing family meals, and outdoor spaces for children to enjoy.

Visitors can easily access nearby attractions such as Lake Cumberland, which offers opportunities for boating, fishing, and swimming. Additionally, the region is dotted with parks and nature trails, ideal for hiking and picnicking.
Can I rent a vacation home with a pool or hot tub in Monticello?
In Monticello, Kentucky, travelers can find a selection of vacation homes available for rent that include pools or hot tubs, with around 10 options to choose from. This charming town is situated near Lake Cumberland, providing a scenic backdrop for a relaxing getaway. Many of these rentals come equipped with private pools, inviting hot tubs, and spacious outdoor areas, ideal for families or groups looking to unwind after a day of exploring the beautiful surroundings.

Travelers can expect amenities such as fully equipped kitchens, comfortable living spaces, and often outdoor patios or decks that enhance the experience of enjoying the tranquil Kentucky landscape.
Can I find long-stay vacation rentals in Monticello?
A long-stay vacation rental in Monticello is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Monticello?
In Monticello, Kentucky, travelers will find a variety of pet-friendly house rentals available, with around 24 options to choose from. Many of these rentals offer spacious living areas, fully equipped kitchens, and outdoor spaces, making them ideal for families or groups traveling with pets. Some properties may feature amenities such as fenced yards, ensuring a safe environment for your furry companions to enjoy the outdoors.

The surrounding area is rich in natural beauty, with opportunities for outdoor activities. Nearby Lake Cumberland is a highlight, offering a range of recreational options like boating, fishing, and hiking. The lake's scenic parks often welcome pets, allowing for enjoyable outings with your four-legged friends. Additionally, Monticello has a friendly atmosphere, with local shops and eateries that may accommodate pets, enhancing the overall experience for travelers.
Are there any remote work vacation rentals in Monticello?
In Monticello, Kentucky, there are plenty of remote work vacation rentals available, with about 63 options to choose from. Many of these properties are equipped with essential amenities for a productive work environment, including reliable Wi-Fi, dedicated workspaces with desks and chairs, and comfortable living areas for relaxation after a day of work.

Travelers can expect a range of accommodations, from cozy cabins to spacious family homes, often set against the backdrop of the beautiful Lake Cumberland region. This area not only offers tranquility for remote work but also recreational opportunities, such as fishing and boating, making it an ideal blend of productivity and leisure. Additionally, the local community features inviting restaurants and shops, providing convenience for those staying in the area. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Monticello vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Monticello with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Monticello?
In Monticello, popular vacation rental amenities cater to travelers seeking comfort and convenience. Most properties feature fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many rentals also include decks or patios, providing a serene outdoor space to relax and enjoy the surrounding nature. Onsite parking is commonly available, which is a significant advantage for those traveling with vehicles. Additionally, rentals often come with coffee and tea makers, and some even include blenders for guests who enjoy making smoothies or other beverages.
When is the best time to visit Monticello for a vacation rental?
The peak travel season in Monticello runs from June to August, with July standing out as the most popular month for visitors. This summer period invites travelers seeking a blend of relaxation and adventure, as the warm temperatures (ranging from the mid-70s to low 90s Fahrenheit) create ideal conditions for outdoor activities, such as hiking and fishing at nearby Lake Cumberland.

During these months, Monticello buzzes with activity, providing ample opportunities for sightseeing and enjoying local events. The vibrant setting is superb for families and groups wanting to make the most of their summer vacations. With various rental options available, you can find accommodations that suit your preferences for quality and convenience.

If you're looking for a more budget-friendly experience, consider visiting in October. This month offers a quieter ambiance, superb for those who prefer a more serene getaway. Witness the beautiful fall foliage and enjoy peaceful walks along the lake, where the autumn colors reflect beautifully on the water.
How early should I book a Monticello vacation rental?
Book your Monticello vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Monticello, Kentucky, United States of America?
In Monticello, Kentucky, visitors can explore a variety of attractions that reflect the area's natural beauty and local culture. One of the main draws is Lake Cumberland, where outdoor enthusiasts can enjoy boating, fishing, and swimming. The scenic views from the surrounding parks and marinas offer a great backdrop for a day of relaxation.

The nearby Daniel Boone National Forest provides ample opportunities for hiking and wildlife viewing, with trails that cater to both casual walkers and more experienced hikers. For those interested in history, the Monticello area features several sites reflecting the region's heritage, including the Wayne County Historical Museum, which showcases local artifacts and exhibits.

Additionally, the local downtown area offers charming shops, restaurants, and cafes, where visitors can sample regional cuisine and shop for unique gifts.
Can I change or cancel my Monticello home rental booking on Vrbo?
To find Monticello vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Monticello vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More Vacation Ideas