Best Vacation Homes in Monticello
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Pet Friendly
- Kitchen
- Parking
GB £105/Night
For 7 Nights GB £738
340.86 ft²
17 Guests
6 Bedrooms
7 Bathrooms
Bed & Breakfast
- Oceanfront
- Fireplace/Heating
- Ocean View
GB £110/Night
For 7 Nights GB £768
1 Bedroom
1 Bathroom
Couples Retreat
Bed & Breakfast
- Fireplace/Heating
- Breakfast
- Parking
GB £115/Night
For 7 Nights GB £808
2800 ft²
10 Guests
6 Bedrooms
2 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Pool
GB £258/Night
For 7 Nights GB £1,806
GB £112/Night
For 7 Nights GB £784
1600 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
GB £211/Night
For 7 Nights GB £1,477
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
GB £239/Night
For 7 Nights GB £1,675
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Hot Tub
- Fireplace/Heating
- Pet Friendly
GB £176/Night
For 7 Nights GB £1,235
Monticello Luxury Rentals
18 Guests
9 Bedrooms
8 Bathrooms
Family Friendly
House
- Air Conditioner
- Internet
- Child Friendly
GB £1,036/Night
For 7 Nights GB £7,254
4000 ft²
15 Guests
4 Bedrooms
3 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
GB £461/Night
For 7 Nights GB £3,227
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
GB £245/Night
For 7 Nights GB £1,716
1400 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
GB £236/Night
For 7 Nights GB £1,651
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
GB £181/Night
For 7 Nights GB £1,265
1 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
GB £179/Night
For 7 Nights GB £1,256
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
GB £162/Night
For 7 Nights GB £1,137
200 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
GB £159/Night
For 7 Nights GB £1,116
Monticello Pet Friendly Vacation Rentals
GB £115/Night
For 7 Nights GB £805
614.89 ft²
22 Guests
31 Bedrooms
4 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- View
- Pet Friendly
GB £52/Night
For 7 Nights GB £366
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
GB £220/Night
For 7 Nights GB £1,538
269.1 ft²
14 Guests
52 Bedrooms
4 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
GB £59/Night
For 7 Nights GB £414
Monticello Large Vacation Homes
14 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
GB £821/Night
For 7 Nights GB £5,748
1500 ft²
10 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Kitchen
- Parking
GB £250/Night
For 7 Nights GB £1,748
Why Choose Rent By Owner for your Monticello Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Monticello
When should you plan your Vacation Rentals stay?
Timing your visit to this charming region ensures you experience its best weather and local events, helping you select the ideal period for booking your Monticello vacation rentals through Rent By Owner and making the most of your stay here.
Peak Season Highlights
Spring (March to May)
During spring, the area experiences pleasant weather, making it an ideal time for outdoor activities and exploring local sights.
Average Temperature Daytime: 75°F - Nighttime: 55°F
Fall (September to November)
Autumn offers mild temperatures and fewer crowds, providing a relaxed atmosphere for your visit.
Average Temperature Daytime: 78°F - Nighttime: 58°F
Off-Season Highlights
Summer (June to August)
In summer, the region sees higher temperatures and humidity, which may suit travelers seeking warm-weather relaxation.
Average Temperature Daytime: 90°F - Nighttime: 70°F
Winter (December to February)
During winter, you can enjoy cooler temperatures and lower visitor numbers, offering a quieter experience in this destination.
Average Temperature Daytime: 60°F - Nighttime: 40°F
Weekly Weather Forecast for Monticello
How to Book Your Monticello Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Monticello
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor pool to relax after exploring the charming town.
- Take advantage of spacious patios or decks perfect for outdoor dining and gatherings.
- Benefit from lush gardens or green spaces that enhance your outdoor experience.
- Make use of barbecue grills for cookouts in the warm regional climate.
- Experience outdoor recreational facilities such as tennis courts or walking trails.
- Sit back and unwind on comfortable lounge areas designed for sunbathing or reading.
- Utilize covered porches or verandas to enjoy the fresh air while staying shaded from the sun.
Top Attractions Around Monticello
What attractions are nearby?
Within this charming area, you can enjoy a variety of outdoor activities such as exploring scenic parks and experiencing local cultural events, all conveniently close to your Monticello vacation rental.
Family Activities
- Florida Nature Preserve Tour: Discover the region's diverse ecosystems and enjoy a guided walk through local nature preserves, perfect for family adventures in this scenic area.
- Historic Downtown Exploration: Stroll through the charming historic district where you can learn about the area's rich heritage and enjoy family-friendly shops and cafes.
- Local Farmers Market Visit: Experience the regional flavors by browsing fresh produce and handmade goods at the weekly farmers market, ideal for a relaxed family outing.
- Community Park Activities: Spend quality time outdoors at the community park with playgrounds, picnic spots, and open fields to keep your family entertained during your stay.
Adult Activities
- Fishing on the Withlacoochee River: You can enjoy a relaxing day of fishing along the scenic river that flows through this charming area, offering great opportunities for both novice and experienced anglers.
- Exploring local art galleries: Discover the vibrant arts scene by visiting the quaint galleries in town, where local artists showcase their creative talents inspired by the region’s natural beauty.
- Golfing at nearby courses: Tee off at well-maintained golf courses just outside here, providing a perfect way to unwind while enjoying the lush landscapes characteristic of the region.
- Participating in nature walks and birdwatching: Spend your days exploring nearby parks and wetlands, ideal for observing native wildlife and experiencing the tranquility of the outdoors in the region.
Other Places to Stay in Monticello, FL
Letchworth-Love Mounds Archaeological State Park
Wacissa
Drifton
Monticello Opera House
Monticello Jefferson County Chamber of Commerce
Monticello Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining and Markets: Take advantage of the region's charming eateries and local markets to enjoy authentic flavors and fresh ingredients during your stay.
- Plan Outdoor Activities: Utilize nearby parks or outdoor spaces for activities like walking, cycling, or picnicking to fully experience the area's natural beauty.
- Visit Historic Sites: Discover the rich history of the destination by visiting notable sites and landmarks that highlight its cultural heritage.
- Choose a Strategic Location: Select vacation rentals situated close to key attractions and amenities to maximize your convenience and exploration time here.
Transportation Options
- Monticello Amtrak Station: This station offers convenient rail travel for visitors exploring the nearby region from across the country.
- Local Taxi Services: Trusted taxi companies provide reliable transportation within and around the area, making short trips to local attractions easy.
- Car Rentals: Several car rental agencies in town give you the flexibility to discover the scenic surroundings at your own pace.
- Bus Services: Regional bus routes connect here with neighboring cities, providing an affordable option for exploring the broader region.
Local Customs Options
- Southern Hospitality: You’ll notice the warm and welcoming attitude of locals here, reflecting the region’s deep-rooted Southern hospitality traditions.
- Historic Courthouse Protocol: Respect for historic sites like the courthouse plays a key role, as it symbolizes the town's preservation of its charming Southern history.
- Religious Festivals: Attending local religious festivals offers insight into the community’s close-knit values and longstanding spiritual customs.
Frequently Asked Questions About Monticello?
1. What are the top 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:
- Cozy Cottage surrounded by antebelllum homes close to downtown.
- Secluded pool home on 4+ acres
- Charming Monticello Retreat: Explore History, Shops, and Local Delights
- Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.
- Elegant 2 Bedroom, 2 Bath Guest House close to Tallahassee. Whole Home Generator
- Historic Cottage - Near FSU & Thomasville
- Camellia Cottage - wheelchair friendly
- Scarlett Room - At Avera-Clarke
- Queen Anne Room at Avera-Clarke
- Dog friendly nature preserve Monticello, FL
2. Which vacation homes in Monticello are best for families?
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:
3. How many Rentbyowner vacation rentals are available in Monticello?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 36 in the Monticello area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Monticello.
4. What is the cancellation policy for vacation rentals in Monticello, Florida?
Cancellation policies vary by property listing; it is important to review the specific terms listed on the property page or contact the owner directly to understand the refund and cancellation conditions for your stay.
5. How do I find available dates and book a vacation rental in Monticello?
You can easily check availability and make reservations through the booking platform by selecting your desired dates and submitting an inquiry or booking request directly on the listing page.
6. Are there any additional fees I should be aware of when booking here?
Additional costs such as cleaning fees, service charges, or taxes are typically detailed on each property’s listing. Be sure to review these details before confirming your reservation.
7. What amenities are usually included in vacation rentals in this area?
Most properties offer essential amenities such as Wi-Fi, kitchen facilities, and parking. For specific features like pools or outdoor spaces, check the individual listing details or contact the host for clarification.
8. Is it safe to stay in a vacation rental in this part of Florida?
The region maintains a reputation for safe and reliable accommodations. For peace of mind, you can read reviews from previous guests and reach out to the property owner with any safety-related questions.
Monticello Top Rated Vacation Rentals
1 ft²
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Bed & Breakfast
- Pool
- Parking
- Internet
GB £146/Night
For 7 Nights GB £1,020
GB £66/Night
For 7 Nights GB £464
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Pool
- Balcony/Terrace
- Kitchen
GB £181/Night
For 7 Nights GB £1,268
