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.

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.

Private Hot tub, Adjusting Kingbed, Gated Property

Read All to get Pet Discount! Walk to Historic District: famous for Ghost Tours, Good eats, Antique shopping, Live theatre, and Music on Fri. Nite @ THE Social. Returning Guests - before booking, send an "inquiry" for 50% Less Pet Fee! Also applies to "One Nite" booking with Pet! - Please Be Sure To Add Pets & Any Guest with you Upon Booking (list service animals as guest for insurance purposes). Pet fees are per stay, not per nite. - Any Smoking: Outside Only! [Medical also outside Only].

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.

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.

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.

Home in Monticello near downtown w/ modern vibes

This entire home has plenty amenities. The 1562 sq ft. corner is home near downtown. The home is cozy, comfortable and functional for humans only. I hope your stay allows you to enjoy your spouse, family, friends or co-workers. Make sure you create lasting memories as you relax, attend college games, graduations, work or just need a nice place to stay. Tallahassee or Thomasville are only a 30-35 minute drive away.

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.

Sienna Lee Gardens: A Beautifully Renovated Home

Relax and unwind in this beautiful 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 swimming pool. 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.

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!