Vacation rentals in Monticello

Private Hot tub, Adjusting Kingbed, Gated Property

Walking distance from Historic district famous for Ghost tours, Good Eats, Antique shopping, Live theatre & Music on wkends! Message any questions! Laundry service available for week or more stays. Planned early check-in/spontaneous late check-out $15 hr. 3 hrs Max. (billed as payment request through app anytime after check-in) Please be sure to add pets to booking! Small BBQ grill & ice cooler; no ice maker. Smoking Outside Only - includes medical! (nico. vape ok) Service dogs are extra guests.

The Cottage at Grand Oaks Plantation

The Cottage on Grand Oaks Plantation is a hidden gem in the small town of Monticello, FL. Nestled under a canopy of 200 year old Live Oaks, you will enjoy relaxing as you watch the horses, ring-tailed lemurs, kangaroos... This restored plantation cottage housed guests in the early 1900's, and is now completely renovated with antique stained glass windows and doors, beadboard walls and a screened wrap around porch. Pool table and darts also. This cottage was featured in Country Living Magazine.

Private updated Cottage, Cozy and Spacious

Escape to this charming, private 1-bedroom cottage with a queen bed and spacious living area—perfect for two! Enjoy stunning lake and orchard views from your cozy retreat, complete with a private picket fence, entrance, and patio area for outdoor relaxation. Fully equipped with all the comforts you need for ultimate peace and quiet. Just 9 miles east of Monticello, 20 minutes from Thomasville, and 35 minutes to Tallahassee. Unplug, unwind, and make unforgettable memories in this nature haven!

Bright, Modern Studio near Downtown & Universities

Enjoy your stay in our cozy, modern studio at a quiet, centrally-located neighborhood. The property is tastefully decorated with colorful patterns and modern accents. You will feel right at home. Downtown and universities are just about a 10-minute drive, and there are vast variety of stores and restaurants on Parkway less than 5 minutes away. One of our favorite cafes, The Bada Bean, serves excellent breakfast and brunch and is just a few blocks down the street (walking distance).

Welcome to The Schoolhouse

This special place is close to everything, making it easy to plan your visit. Discover this fully renovated 1926 two-bedroom gem in the heart of Monticello, Florida. Named for one of two schoolhouses originally associated with the church now housing Monticello’s Chamber of Commerce, the home still reflects its history. From reclaimed hardwood floors to refurbished original windows, doors, and moldings, you can experience the best of modern amenities and historic charm.

Fern Hollow Acres A peaceful retreat in the woods

Three bedroom lodge style house nestled in the woods in a retreat setting. Forget your worries in this spacious and serene space. Lovely grounds to walk around , enjoying deer, rabbits, owls and the occasional fox Butterfly, bees and bird sanctuary. Just 30 minutes to FSU/FAMU and the Florida Capitol. Twenty minutes to historic Monticello, Fl A short drive to the headwaters of the Wacissa River county park.with kayak and canoe rentals.

Maple Tree Cottage - close to downtown

Forget your worries in this simple and serene space. Just a short walk and you'll be enjoying all the charm that downtown Thomasville has to offer. Our home welcomes you with 2 bedrooms, each with queen size beds, and 1 bathroom. All of your day-to-day conveniences are available in our home allowing you to settle in like it's yours. The home is located just blocks away from all of the shopping and restaurants on Broad Street.

King Bed-Pets -Quiet-Huge fence Yrd

Unwind in this spacious, equestrian-themed retreat in a peaceful upscale country setting! Set on a large fenced lot, this dog-friendly home offers comfy new beds, Roku TVs in every bedroom, and all the amenities you’d expect. Enjoy shuffleboard, gather outdoors, or relax with easy access thanks to the 2-car garage with remote. Plenty of room to roam and recharge—perfect for a serene getaway just outside the city buzz.

Charming cottage located on a historic street.

The Camelia Cottage is located on charming Pearl Street, surrounded by historic antebellum homes. Enjoy quiet evenings in this unique neighborhood. Camelia Cottage is within 30 minutes of Tallahassee and within walking distance of quaint shops and restaurants. You will certainly enjoy the small town atmosphere. Camelia Cottage has recently been updated, there are two beds one king and one full bed.

Gardenview Tiny House

Enjoy the sounds of nature when you stay in this unique tiny home in a garden setting. Quiet and private neighborhood. Our Tiny House space is perfect for one guest and cozy for two. We are located about 8 miles (15 to 20 minutes by car) from the Forida Capitol Building and the FSU Campus. We offer a 15% discount for bookings of 7 days or more, and 40% discount for 28 days or more.

Executive Suite on Park Ave.

This is the most elegant and tranquil 1250 Sq ft. of pure comfort! It features a library quiet central smart H & A. system (not a window air) can be set to 70 in the summer and 68 in the winter. Large one bedroom with a Tempur-pedic luxury king size bed . 7 ft glass shower . Sofa can be used as an Extra long twin. Full kitchen with dishwasher

Dogwood House; Private 2 Bedroom in Monticello, FL

Charming 1950s Florida Bungalow in Historic Monticello Florida Stay at The Dogwood House—a beautifully restored bungalow just steps from downtown shops, dining, and drinks. Pet-friendly for well-behaved pups, this cozy retreat is the perfect mix of comfort and charm. Only 30 minutes to Tallahassee or Thomasville!