Holiday houses 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.

Beautiful Guest House in Desirable Northside

Hello and welcome to our home! This guest house is in our backyard and is very cozy with a large, screened-in porch. Sit in a rocking chair on the porch and enjoy the sounds of the many birds and the company of butterflies and hummingbirds. The King size bed is so comfortable! Our neighborhood lies between the Market District to the south and Bannerman Crossing to the North. There is shopping as well as many restaurants all around us. Downtown and FSU are 20 min away depending on traffic.

Apartment on Jefferson

This one bedroom apartment is located in the back of an early 1900's house. Private entrance, hardwood floors, high ceilings, large kitchen and living space, full bathroom, bedroom with walk in closet. WiFi, Washer/Dryer, and dishwasher. This property is perfect for travel professionals. 30 min. to SGMC, and 30 min. to Archibold in Thomasville, 5 min. or less from Brooks Co. hospital and Presbyterian nursing home. The pet fee is 50.00 and listed under additional charges on the booking page.

Private, Hot tub, Adjustable King, Gated Property!

Please read all check-in instructions!! 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!

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.

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