Monticello Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Monticello holiday rentals

Interior
Camellia Cottage - wheelchair friendly

Cottage in Monticello

Camellia Cottage - wheelchair friendly
10.0 out of 10, Exceptional, (8)
"Great location, clean, and comfortable. "
United States
Teresa
The price is HK$762
HK$1,592 total
includes taxes & fees
11 Jan - 12 Jan 2026
Camellia Cottage - wheelchair friendly
Interior
Dog friendly nature preserve Monticello, FL

Mobile Home in Monticello

Dog friendly nature preserve Monticello, FL
10.0 out of 10, Exceptional, (1)
"Quiet and relaxing spot. Very well maintained and clean. Wonderful hosts. My only regret is that we couldn't stay longer."
United States
KARL L.
The price is HK$1,361
HK$1,691 total
includes taxes & fees
31 Dec - 1 Jan 2026
Dog friendly nature preserve Monticello, FL
Fridge, microwave, oven, stovetop
Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.

Holiday Home in Monticello

Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.
10.0 out of 10, Exceptional, (16)
"Clean great location and very friendly thank you for the stay we will be back"
United States
ROBERT B.
The price is HK$1,089
HK$2,469 total
includes taxes & fees
4 Jan - 5 Jan 2026
Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.
Outdoor dining
Reel Pelican Paradise located in Paradise village, Shellpoint Beach on the Gulf

Mobile Home in Crawfordville

Reel Pelican Paradise located in Paradise village, Shellpoint Beach on the Gulf
10.0 out of 10, Exceptional, (74)
"Very nice. Very clean and well cared for property."
United States
Russell or Tyler
The price is HK$945
HK$2,332 total
includes taxes & fees
4 Jan - 5 Jan 2026
Reel Pelican Paradise located in Paradise village, Shellpoint Beach on the Gulf
Property grounds
Enjoy Crawfordville at the Courtyard’s Oyster Cottage

Cottage in Crawfordville

Enjoy Crawfordville at the Courtyard’s Oyster Cottage
10.0 out of 10, Exceptional, (55)
"Very modern looking on the inside, it really was a nice place!"
United States
Ricky
The price is HK$441
HK$1,298 total
includes taxes & fees
4 Jan - 5 Jan 2026
Enjoy Crawfordville at the Courtyard’s Oyster Cottage
Property grounds
Cozy Guest house - Near FSU, Trails, and the airport.

Apartment in Tallahassee

Cozy Guest house - Near FSU, Trails, and the airport.
2.0 star property
10.0 out of 10, Exceptional, (1)
"I had the most wonderful stay here! It’s super cute and cozy! From the moment I arrived, I felt right at home. The space was spotless, thoughtfully decorated, and full of charming touches that made it truly special. The bed was incredibly comfortable, the lighting was warm and inviting, and every little detail—from the soft blankets to the well-stocked kitchen—showed how much care went into creating a relaxing environment.The location was perfect too: peaceful and quiet, yet close enough to...
United States
Beth H.
The price is HK$583
HK$1,118 total
includes taxes & fees
25 Jan - 26 Jan 2026
Cozy Guest house - Near FSU, Trails, and the airport.
Fridge, microwave, oven, stovetop
Enjoy Crawfordville at the Courtyard’s Pelican Cottage.

Cottage in Crawfordville

Enjoy Crawfordville at the Courtyard’s Pelican Cottage.
10.0 out of 10, Exceptional, (126)
"Cozy, very clean. Stay here twice a year while visiting family. Perfect location. "
United States
Faye D.
The price is HK$665
HK$1,504 total
includes taxes & fees
5 Jan - 6 Jan 2026
Enjoy Crawfordville at the Courtyard’s Pelican Cottage.
Courtyard
stayAPT Suites Tallahassee-Capitol

Aparthotel in Tallahassee

stayAPT Suites Tallahassee-Capitol
4.0 star property
9.0 out of 10, Wonderful, (65)
"Everything was great! Nice room"
United States
Jennifer
The price is HK$805
HK$906 total
includes taxes & fees
28 Dec - 29 Dec
stayAPT Suites Tallahassee-Capitol
Interior
Scenic beauty on the bay

Holiday Home in Crawfordville

Scenic beauty on the bay
2.0 star property
10.0 out of 10, Exceptional, (1)
"Mark was a phenomenal host. Great communication, transparency, and hospitality. We enjoyed our time and look forward to the next visit!"
United States
Katelyn B.
The price is HK$554
HK$1,111 total
includes taxes & fees
5 Jan - 6 Jan 2026
Scenic beauty on the bay
Fridge, microwave, oven, stovetop
Mimosa Getaway - Less than 1 mile from Downtown

Holiday Home in Thomasville

Mimosa Getaway - Less than 1 mile from Downtown
2.0 star property
9.6 out of 10, Exceptional, (11)
"The house was very comfortable and clean, also close to downtown area "
United States
rushawn h.
The price is HK$778
HK$2,519 total
includes taxes & fees
11 Jan - 12 Jan 2026
Mimosa Getaway - Less than 1 mile from Downtown
Living area
Relaxing Retreat House on Chateau Lane 2 Bed/2 Bath near FSU and FL Capital

Holiday Home in Tallahassee

Relaxing Retreat House on Chateau Lane 2 Bed/2 Bath near FSU and FL Capital
9.6 out of 10, Exceptional, (4)
"This was a perfect place to stay for a FSU game. We could make simple meals and we weren’t caught up in the craziness of Tallahassee. We were two couples, each of us had a bedroom & bath. Nice living area with Roku tv. "
United States
Terry W.
The price is HK$560
HK$1,485 total
includes taxes & fees
31 Dec - 1 Jan 2026
Relaxing Retreat House on Chateau Lane 2 Bed/2 Bath near FSU and FL Capital
Smart TV
Private Garden Retreat - King Bed - mins TMH + Downtown + FSU!

Apartment in Tallahassee

Private Garden Retreat - King Bed - mins TMH + Downtown + FSU!
2.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect location. Lovely place, clean, everything you need. "
United States
Paul M.
The price is HK$628
HK$1,387 total
includes taxes & fees
5 Jan - 6 Jan 2026
Private Garden Retreat - King Bed - mins TMH + Downtown + FSU!
Outdoor dining
An elegant waterside retreat in the Red Hills

Cabin in Thomasville

An elegant waterside retreat in the Red Hills
9.8 out of 10, Exceptional, (24)
"Very nice property. Good amenities. Keurig didn’t work well, no good directions fot direct tv. Cabin very clean, wonderful setting at end of gravel road. Great wildlife, including the mouse which came to visit. Recommend highly. "
United States
michael
The price is HK$739
HK$2,384 total
includes taxes & fees
12 Jan - 13 Jan 2026
An elegant waterside retreat in the Red Hills
2 bedrooms, iron/ironing board, WiFi, bed sheets
Mimosa Cottage - Near Downtown Thomasville

Holiday Home in Thomasville

Mimosa Cottage - Near Downtown Thomasville
10.0 out of 10, Exceptional, (12)
"This was a very nice property. It had everything you need for a comfortable stay! The owners were also very easy to get ahold of. Thank you for a nice stay!"
United States
Catherine
The price is HK$747
HK$2,323 total
includes taxes & fees
4 Jan - 5 Jan 2026
Mimosa Cottage - Near Downtown Thomasville
TV, offices
The Budget Friendly Home

Holiday Home in Tallahassee

The Budget Friendly Home
2.0 star property
10.0 out of 10, Exceptional, (1)
"Definitely our host!!"
United States
Shannon T.
The price is HK$622
HK$1,468 total
includes taxes & fees
2 Jan - 3 Jan 2026
The Budget Friendly Home
TV, offices
Enjoy Space and Privacy in this Master Bedroom

Holiday Home in Tallahassee

Enjoy Space and Privacy in this Master Bedroom
2.0 star property
The price is HK$373
HK$842 total
includes taxes & fees
25 Jan - 26 Jan 2026
Enjoy Space and Privacy in this Master Bedroom
Interior
New-1 Mile to FSU-Artsy Tree-House

Holiday Home in Griffin Heights

New-1 Mile to FSU-Artsy Tree-House
2.0 star property
9.8 out of 10, Exceptional, (8)
"Nice, whimsical place. Clean…felt like a treehouse. "
United States
Rob G.
The price is HK$424
HK$1,289 total
includes taxes & fees
5 Jan - 6 Jan 2026
New-1 Mile to FSU-Artsy Tree-House
Dining
Studio ESCAPE Cozy CLOSE-IN Kitchen Pool Work-Space

Apartment in Tallahassee

Studio ESCAPE Cozy CLOSE-IN Kitchen Pool Work-Space
10.0 out of 10, Exceptional, (92)
"The property was nice, warm, and inviting."
United States
Mark
The price is HK$574
HK$932 total
includes taxes & fees
5 Jan - 6 Jan 2026
Studio ESCAPE Cozy CLOSE-IN Kitchen Pool Work-Space
TV, books
Lovely guesthouse near I10 with grand piano; 15 min from campus

Holiday Home in Killearn Estates

Lovely guesthouse near I10 with grand piano; 15 min from campus
10.0 out of 10, Exceptional, (7)
"Excellent... Could not have been better."
United States
Donald
The price is HK$739
HK$1,718 total
includes taxes & fees
7 Jan - 8 Jan 2026
Lovely guesthouse near I10 with grand piano; 15 min from campus
Dining
Tally Town Gem: 2BR/2BA Townhome, Sleeps 6!

Holiday Home in Tallahassee

Tally Town Gem: 2BR/2BA Townhome, Sleeps 6!
2.0 star property
The price is HK$506
HK$1,261 total
includes taxes & fees
14 Jan - 15 Jan 2026
Tally Town Gem: 2BR/2BA Townhome, Sleeps 6!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Monticello Hotel Reviews

Econo Lodge

Econo Lodge

10/10 Excellent
"Place was great. "
Ronald 1-night trip
Posted 1 day ago
Econo Lodge

Find out more about Monticello

Search for holiday rentals in Monticello on Expedia! You can easily find your home rentals, villas, holiday apartments in Monticello using one of the methods below:

  • View our selection of featured holiday rentals in Monticello
  • Use the map to find apartments and other holiday homes in the Monticello neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Monticello while they last

Look no further and take a look at our great range of rental properties in Monticello!

Frequently asked questions

Can I find holiday rentals in Monticello?

Yes, there are holiday rentals close to the most popular sights in Monticello, or you can select a more secluded option if you're looking for a relaxing stay. Monticello is known for its football games and coffee shops. Make sure you have time to check out the wineries while you're in the area.

What are some of the best holiday rentals that Monticello has to offer?

Canal-front home at Shell Point. Relax. Fish. Explore. Swim. Amazing Sunsets!: This holiday home rental outside of Monticello offers a garden, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Monticello?

Expedia has 13 holiday rentals for your stay in Monticello.

What’s there to see and do in Monticello?

"Boots" Thomas Veteran Memorial Park and Jordan Memorial Park are a couple of scenic spots to enjoy the outdoors, whereas Monticello Opera House is one of the cultural attractions. While here, St. Marks River Preserve State Park and Jefferson Country R. J. Nailer Public Library are other places worth a visit.

What’s a holiday rental in Monticello like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Monticello. Holiday rentals offer amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for family trips.