Holiday houses in Monticello

Live Oak Cottages II InTown-Nature Retreat

Private long driveway to a quiet setting. Beautiful Live Oak trees around the grounds. It’s the upstairs cottage apartment with tall windows giving you a view to the Live Oak trees canopying together. The one by the cottage is 200 +years old!! Charming and cozy place to relax or work! Living room windows are tinted for privacy. Comfy bed and all the bedding is cleaned in between guests. There are plenty of towels, linens, and the essentials you need to be comfortable. Smart tv and Wifi too

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.

Cozy Country Cottage - Waterfront!

Enjoy the sounds of nature when you stay in this unique country cottage on private Turkey Pond. Deer, turkey & raptors are just some of the wildlife you may encounter. Stunning sunsets are common & kayaks are on hand for a paddle. There is outdoor seating & a sun umbrella for the porch and stars twinkle on clear nights. Special touches make your stay comfy & cozy including on-demand hot water, a luxurious queen bed w/ a cozy comforter, mini-split heat/ac, dish network, smart tv & much more.

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!

Vickie's Hideway

Hideaway says it all, Located in a peaceful beautiful country setting. You have 1 acre to sit back, relax, and enjoy what Mother nature has to offer and just a short drive back to Tallahassee for all the amenities of the city. Nearest Walmart - 8 miles Capital Regional Hospital (CRMC) - 12 miles Tallahassee Memorial Hospital - 13 miles Tallahassee Regional Airport - 17 miles Donald Tucker Civic Center - 12 miles Doak Campbell Stadium - 13 miles

Shangri-La Treehouse

Shangri-La Treehouse is the 1st and only luxury treehouse in Tallahassee, Florida's Capital City. Nestled between ancient oaks, Shangri-La Treehouse is luxury in the wild where serenity is found. You are invited to enjoy 9.5 acres of verdant land amidst ducks, deer, owls, and other assorted wildlife that call Shangri-La home. A thoughtful, adults only (21+) romantic getaway for 2 that can accommodate up to 4 guests comfortably.

Private Hot tub, Adjusting Kingbed, Gated Property

Please read all! Walking distance from Historic District that's famous for Ghost tours, Good Eats, Antique shopping, Live theatre & Music on weekends! BE SURE TO ADD PET & Any Guest with you UPON Booking! (list service animals as guest). [Smoking Outside Only - medical as well!!!] Pet Fees are per stay - Reduced for returning guests - send booking inquiry 1st to get 50% discount; also given to 1 night booker with 1 pet.

small town living

Enjoy the laid back. simple, life of a small southern town. Our old house with hardwood floors, nice comfortable furniture, and vintage decorating choices is perfect for a leisurely get away or business. Great stay for travel nurses or others working temporarily in the area, or just a layover during travels. An air mattress and pack and play are also available. We do allow pets with a pet fee and rules.