Monticello Holiday Rentals

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Monticello

stayAPT Suites Tallahassee-Capitol

4.0 star property
stayAPT Suites Tallahassee-Capitol

Coastal Getaway on canal-steps to the beach

10.0 out of 10, Exceptional, (43)
"The place was cozy and comfortable. It is must bigger than the pictures show. Outdoor shower area is awesome to clean up after fishing or day at the beach."
Coastal Getaway on canal-steps to the beach

ROOF DAMAGE FROM HURRICANE Florida Waterfront Home, Fishing & Pet Friendly

9.6 out of 10, Exceptional, (113)
"Perfect location! Far enough from everywhere to relax but close enough when needed. Everything we needed was there."
ROOF DAMAGE FROM HURRICANE Florida Waterfront Home, Fishing & Pet Friendly

Shell Point Beach 2BR condo with marina views

9.8 out of 10, Exceptional, (9)
"Consider purchasing new pillows for bed area."
The price is HK$1,331
HK$2,159 total
includes taxes & fees
24 Nov - 25 Nov
Shell Point Beach 2BR condo with marina views

Central 4 bedroom 3 bathroom townhome! 5 mins to FSU, 10 mins to the hospital.

9.4 out of 10, Exceptional, (3)
"Convenient place for homecoming"
Central 4 bedroom 3 bathroom townhome! 5 mins to FSU, 10 mins to the hospital.

Relax on a Beautiful River in a Natural Florida Setting

10.0 out of 10, Exceptional, (217)
"It was a great few days getaway from civilization. The view of River was beautiful and being in the middle of a forest was so peaceful and quiet I love rustic, and that satisfied my appetite "
Relax on a Beautiful River in a Natural Florida Setting

ON BEACH! Beautifully decorated. Everything you need! Beach toys firepit kayaks

10.0 out of 10, Exceptional, (28)
"We had 2 families and we all had a great time. Sue was very attentive and checked on us several times to make sure we had everything we needed. We were able to check in early which was amazing. House was very well stocked with everything you could possibly need. We enjoyed being steps away from the beach. Beach is not crystal clear with white sand but it was great for fishing and everyone in our group still enjoyed the beach. Thank you for having us and I'm sure we will be back!"
ON BEACH! Beautifully decorated. Everything you need! Beach toys firepit kayaks

Lakefront southern charm in beautiful quiet area

10.0 out of 10, Exceptional, (137)
"Loved the house for the eight of us staying. Plenty of space for us to all hang out and also have our own privacy when wanted. Kids loved the lake to paddle board and swim. "
Lakefront southern charm in beautiful quiet area

Waterfront Panacea Vacation Rental w/ Dock!

9.0 out of 10, Wonderful, (4)
"Loved the house and location. It was peaceful, quiet, the house was clean and we all enjoyed spending time outside on the dock. Would most definitely rent again! "
Waterfront Panacea Vacation Rental w/ Dock!

4 Mi to Dtwn: Pet-Friendly Abode in Tallahassee!

9.2 out of 10, Wonderful, (13)
"The property was exactly as listed, and the host was accommodating, very easy to communicate. Good location, easy access to FSU, which we were visiting. A few miles from campus but not inconvenient. Beds were comfortable. Overall, the place was clean and odor free. We were pleased with the rental. My mother, who was my travel partner, has Parkinsons disease. This was a good place for her. There are no steps into the building, a ground floor bedroom, and minimal carpet. She did need to...
4 Mi to Dtwn: Pet-Friendly Abode in Tallahassee!

COZY, QUAINT, COTTAGE

9.8 out of 10, Exceptional, (11)
"Cute place, they were very responsive with questions. Checkin was easy and I was close to where I needed to be, could have my dogs with me, and at a reasonable price."
COZY, QUAINT, COTTAGE

Blue Heron House, Blue Heron House

10.0 out of 10, Exceptional, (17)
"Enjoyed our stay at the Blue Heron House. Very clean and comfortable. Check in was easy. Simple, no frills home but met our needs perfectly. Beds were very comfortable and linens and towels very nice. Only steps away from pool and tennis courts and close to the beach as well. Dock was great for boating. Fishing was great during our visit. Grounds very well maintained. Close to some great eating spots. Very scenic area. Local festivals were a bonus! Communication with owner was top...
Blue Heron House, Blue Heron House

Waterfront -Beautiful sunsets, great fishing, scalloping & bird watching

10.0 out of 10, Exceptional, (40)
"Great place for a weekend getaway "
Waterfront -Beautiful sunsets, great fishing, scalloping & bird watching

Peaceful Country Getaway Pet Friendly and Cozy!

9.4 out of 10, Exceptional, (29)
"Cute little place, secluded and private with screened porch perfect for relaxing in the evening after an eventful day. Close to dollar general for needs. Comfortable sleeping.isa got back to us within minutes for any questions. Extremely satisfied and would highly recommend"
Peaceful Country Getaway Pet Friendly and Cozy!

WATERFRONT Home - Dolphins, Sunsets, Fishing, Kayaks, Canoe, Wildlife

9.8 out of 10, Exceptional, (135)
"We thoroughly enjoyed our too short stay at your home. The house was very well provided with everything we needed. My wife was especially appreciative of the elevator! I enjoyed the kayaks, and caught some nice sea trout and redfish. Peaceful and quiet, saw an alligator, and enjoyed watching the dolphins play and feed from the balcony. Perfect for two mostly retired couples to get together for a reunion."
WATERFRONT Home - Dolphins, Sunsets, Fishing, Kayaks, Canoe, Wildlife

Y Worry! Old Florida Waterfront! Beach, bike trails, boat ramp, fish, & fire pit

10.0 out of 10, Exceptional, (22)
"I am in this beautiful part of florida 2-3 times a year. first time staying at Y Worry but certainly not the last time. love the location. "
Y Worry! Old Florida Waterfront! Beach, bike trails, boat ramp, fish, & fire pit

Peace on the river. Wakulla springs nearby. Wakulla River adjoins property’.

10.0 out of 10, Exceptional, (19)
"The cabin suited our needs. The fire pit was very nice. "
Peace on the river. Wakulla springs nearby. Wakulla River adjoins property’.

Tally Glamping Farmstay GIMPY’S GEODOME with mini horses, goats, cows, chickens

9.8 out of 10, Exceptional, (6)
"Hosts are excellent. They responded quickly and were very friendly and informative. What you see in pictures on VRBO site is what you get. One community restroom (one toilet and sink) and one community shower space. If you like rustic camping and animals and chickens and guineas, you will love this space. Inside of yurk was clean. Outside needs a little more attention. Bring a flashlight. "
The price is HK$537
HK$1,005 total
includes taxes & fees
1 Dec - 2 Dec
Tally Glamping Farmstay GIMPY’S GEODOME with mini horses, goats, cows, chickens

Waterfront Escape w/ Balcony on Shell Point Beach!

10.0 out of 10, Exceptional, (29)
"This was our second time at this rental. come Spring we will be back at least two more times. "
Waterfront Escape w/ Balcony on Shell Point Beach!

Enjoy Crawfordville downtown convenience at the Courtyard’s Pelican Cottage.

10.0 out of 10, Exceptional, (97)
"The cottage was very clean and nicely decorated. Plenty of space for a family of four/five. We would stay here again!"
The price is HK$677
HK$1,518 total
includes taxes & fees
24 Nov - 25 Nov
Enjoy Crawfordville downtown convenience at the Courtyard’s Pelican Cottage.
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.
Don't see what you're looking for?
See all available properties in Monticello
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Monticello you may be interested in

Econo Lodge

2.0 star property
7.4 out of 10, Good, (742)
"Running from Cat 4 Hurricane Milton. It was the last room available, so we were pleasantly surprised that the room was so clean and comfortable! We did not arrive till after 1am but the clerk called somewhere around midnight to make sure we were still coming! It was nice to be assured our room would be available when we finally got there!!!"
The price is HK$655
HK$720 total
includes taxes & fees
10 Dec - 11 Dec
Econo Lodge

Drury Plaza Hotel Tallahassee

3.0 star property
9.8 out of 10, Exceptional, (699)
"The staff is super friendly!"
The price is HK$876
HK$985 total
includes taxes & fees
1 Dec - 2 Dec
Drury Plaza Hotel Tallahassee

Country Inn & Suites by Radisson, Tallahassee-University Area, FL

2.5 star property
8.2 out of 10, Very good, (1090)
"Muy bien"
The price is HK$710
HK$798 total
includes taxes & fees
27 Nov - 28 Nov
Country Inn & Suites by Radisson, Tallahassee-University Area, FL
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.

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?

Coastal Getaway on canal-steps to the beach: This holiday home rental outside of Monticello is located by the ocean, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

How many holiday rentals will I find in Monticello?

Expedia has 11 holiday rentals for your stay in Monticello.

What’s there to see and do in Monticello?

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