Holiday rentals in Monticello

Cabin on Lake Nichols

Enjoy a comfortable retreat in a historic 1930s cabin overlooking a 350-acre private lake. This fully renovated farmhouse features its original beadboard. The historic touches, combined with all the modern amenities, make this the perfect destination for those seeking to enjoy a getaway into nature and fishing experience. The lake is loaded with largemouth bass, catfish, speckled perch, bream, and bluegill and is only otherwise available by very limited membership. See more on IG @lake_nichols

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.

3 miles to FSU-Upper Midtown Luxe-Prime Location

This is a renovated 2BR 1 Bath apartment on the first floor located central off Meridian, a Canopy Road, in Tallahassee, just a short ride or walk to shopping, Whole Foods, Riccardos, ABC, Publix, Walmart, Food Glorious Food, Winthrop Park, Planet Fitness and hundreds of nearby restaurants and coffee shops, wide well maintained sidewalks take you to Lake Ella just 1.5 miles south. About 2.5 miles to the Capitol Building,. Walk to the Tallahassee Aquatic Center less than a mile or several parks.

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.

King bed-Office-Pet-Fenced Yard-Fast WiFi

Welcome to our charming Bo-ho retreat! This 3-bed, 2-bath dog-friendly house is a Bo-ho lover's dream. Step into a world of relaxation as you immerse yourself in the carefully curated Bohemian Decor. Unwind in the cozy living room or whip up a delicious meal in the fully equipped kitchen. The bedrooms are comfortable and tranquil. Outside, the private and spacious fenced-in yard is perfect for your fur babies to roam freely. Come experience the harmony and beauty of this perfect Bo-ho getaway.

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.

Twisted Pine Lake Cabin, secluded & near town

Close to everything, a million miles away....... Down the two-track driveway, past the view of the nearest neighbors, our new custom cabin awaits. Rest easy on the screened porch, with its view of the two-acre lake or cross the adjacent foot bridge to the island. Fish for bass and bream, stroll the walking path, paddle around and enjoy the wildlife, or just relax far from the madding crowd. This slice of paradise sits on 12 acres; our home is across the lake, out of sight and out of mind.

The Carriage House

Our lovely French inspired guest house features an open floor plan, 12-foot ceilings with real wood beams, a fully equipped kitchen and large brick patio overlooking a spacious backyard with shared pool. The two bedrooms are connected by a jack and jill bathroom featuring a tub/shower combination. the second bathroom, located just down the hall, has a standup shower. For additional guests, there are more sleeping arrangements in the family room on a single bed pullout love seat.

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.

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!

The Greywood | A Blackhouse Property

There’s a moment - often within the first few minutes - when your shoulders drop. Your breathing slows. And you realize how tired you’ve been. That moment is why we exist. The Blackhouse brand was created as a response to modern life: the noise, the pace, the constant pull on your attention. Our homes are designed to help you slow down, reset, and reconnect. Here, the goal isn’t escape - it’s restoration. A return to yourself. May you find rest, - Blackhouse

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.