Holiday rentals in Monticello

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.

Edgewood Cottage

Whether you're in town for an event or looking for a getaway, you'll feel cozy, comfortable, and right at home in this historic cottage. Built in 1916, the home offers historic charm and modern amenities. With more than 1,600 sq. ft. and three bedrooms, there's room for the whole family! There's a huge fenced-in yard and Macintyre Park is just half a block away. The front porch and back deck offer serenity under the pines. Or take a 3 minute drive to experience all that downtown has to offer.

Shamrock Street Sanctuary for 7 - 3 Bed 2.5 Bath

Beautiful townhome in a well established, quiet, family neighborhood! This home offers a split floor plan with the main living areas (kitchen, dining, living room, and half bath) downstairs and 3 spacious bedrooms upstairs. The master features a king size bed and private bathroom. There are two additional bedrooms (one with a twin over full size bunkbed and one with a queen sized bed and traditional desk/workspace) that shares a hall bathroom with a stand up shower and double vanities!

Guest house, Hot tub & King Bed on Gated Property!

Please read all check-in notes! Near Hwy 19 i10 exit- 2 exits East of Florida's Capitol. Historic Downtown featuring large ole Southern homes — famous for ghost tours! Message for any questions! Please add any pet to booking! You won't have control of thermostat, but keeping it on 68 these days, as it's downstairs. Quaint little town with good eats, antique shopping, live music & live theatre on weekends! Small BBQ grill. Laundry service available for a week or more stays.

The Knotted Oak Cottage- Fenced & Dog Friendly

Enjoy this cozy “dog friendly” 2 BR cottage on a quiet residential street in the heart of Monticello’s historic district. This cottage is an easy walk to downtown and is ideal for couples or friends for a relaxed getaway. Well-behaved potty trained dogs ( max 2) are welcome! The cottage has a fenced in yard and is located on a perfect street for dog walking. The cottage front porch is the perfect place to unwind with a cocktail before walking to dinner. On Instagram too!

The Shed-King Bed-Boho - Cabin- Grand Piano- WiFi

The Shed is located in a sprinkle of country, splash of city, Thomasville, GA. The Shed hosts a king bed and a combined kitchen living room space with a pullout Queen couch. You can spend your evenings outside on the patio with a fire or explore the beauty of historic downtown only 5 minutes away! A private 2 room guest house with a unique modern flare. No contact, keyless entry on arrival and a cozy, safe, clean space for your get away! We look forward to hosting you!

Private/Entire Studio, Private Keyless Entry

"Private Entrance" 2nd-story STUDIO w/lots of windows. Wood floors, central AC/heat, 1/2 bath, queen bed with new mattress, fridge, Krueig, microwave, WIFI, TV, closet space, ROBES FOR PRIVATE OUTDOOR HEATED SHOWER and towels. Established neighborhood less than 2 miles from FSU and downtown; 1 block to Tallahassee Memorial Hospital. Restaurants under 1/2 mile! It is on our property and we personally clean the studio. Go Noles!

Sienna Lee Gardens: A Beautifully Renovated Home

Relax and unwind in this beautifully renovated 4 bedroom/3 bath home nestled on 20 acres of picture perfect live oaks, organic blueberry orchard, and abundant wildlife. There are so many places for entertaining including a large heated swimming pool (heated from March-Nov). There's a fully equipped kitchen, luxury beds and hotel quality linens. Every room has cable TV and internet throughout the house.

Executive Suite on Park Ave.

SUMMER PRICING SPECIAL 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