Vacation rentals in Monticello

4.94 out of 5 average rating, 132 reviews

The entrance features a charming pathway lined with carefully arranged stones, leading to a welcoming porch adorned with white wooden doors. Lush greenery and shrubs frame the space, providing a serene atmosphere, while the screened-in porch invites relaxation under the surrounding trees.

Cottage 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.

4.86 out of 5 average rating, 325 reviews

The guest house is nestled in a lush green setting, featuring a large screened-in porch illuminated by soft outdoor lighting. The exterior displays a blend of dark wood and light accents, with a welcoming entrance door and surrounded by well-maintained garden space.

Guesthouse in Killearn

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.

4.98 out of 5 average rating, 106 reviews

Home in Tallahassee

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.

A welcoming entrance features a white wooden facade with a classic porch. Two rocking chairs sit on a brick pathway leading to a front door adorned with a wreath. Sunlight filters through nearby trees, creating a serene outdoor atmosphere.

4.95 out of 5 average rating, 138 reviews

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.

5 out of 5 average rating, 100 reviews

A wooden cabin with a screened porch is set in a lush green landscape. Surrounding trees provide dappled shade, while colorful flowering plants enhance the serene atmosphere. The cabin features a metal roof and is partially obscured by greenery, emphasizing the secluded environment.

Cabin in Tallahassee

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.

4.93 out of 5 average rating, 106 reviews

A cozy living room features a comfortable reclining couch and recliner, complemented by a cowhide rug on the floor. Decor elements reflect a Western theme, including artwork of horses on the wall. Natural light enters through a nearby window, enhancing the inviting space.

Home in Berlin

Western Home in the Heart of Berlin, Georgia

Welcome to our inviting Airbnb in Berlin, GA! Immerse yourself in the rustic charm of our western inspired home. Step outside onto the patio area, where you can bask in the fresh air and soak up the Georgia sunshine. And for the ultimate relaxation experience, indulge in a soothing soak in our hot tub. Whether you're savoring morning coffee on the patio or unwinding in the hot tub after a day of exploration, our rental offers the perfect blend of comfort and tranquility for your getaway.

4.89 out of 5 average rating, 128 reviews

A charming cottage is presented, featuring a covered front porch and multiple windows that allow natural light to fill the interior. Lush greenery surrounds the home, enhancing its inviting appearance. Spanish moss drapes from nearby trees, adding to the serene atmosphere of the property.

Cottage in Monticello

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!

5 out of 5 average rating, 10 reviews

The exterior of a charming two-bedroom home features a light blue façade with white accents. A covered entryway provides shelter, while a stone pathway leads to the porch. Lush green grass surrounds the house, complemented by landscaping and a tree offering shade.

Home in Monticello

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.

4.97 out of 5 average rating, 477 reviews

A spacious living area features a comfortable sofa and a wooden accent chair. Natural light enters through double doors, highlighting a piano and various decorative plants. The ceiling showcases exposed beams, and neutral tones create a relaxed atmosphere, complemented by a minimalist TV console.

Cottage in Thomasville

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!

A well-lit bedroom features a queen size bed with white linens and plush pillows. Two windows with light curtains allow natural light to enter. A dark wood dresser and a small accent table are positioned beside the bed, while a ceiling fan adds a modern touch.

4.99 out of 5 average rating, 103 reviews

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.

5 out of 5 average rating, 63 reviews

The charming bungalow features a welcoming front porch with white railings, surrounded by a well-maintained lawn. Mature trees offer shade, and the home's warm exterior blends harmoniously with the lush, green landscape.

Home in Monticello

Private 2 Bedroom Bungalow in Monticello FL

Relax. Take a breath of fresh air and enjoy this beautifully restored 1950's Florida Bungalow in the heart of Historic Monticello, FL! The charming Dogwood House is lovingly furnished to provide a wonderful stay for you and your well behaved/potty trained dogs. Located within walking distance to Monticello's fabulous downtown. Shop, eat, drink, & enjoy! Approximately 30 minutes to Tallahassee or Thomasville.

5 out of 5 average rating, 150 reviews

The charming exterior of the home is framed by large live oak trees, providing shade and a serene setting. A wide porch, bordered by white railings, invites relaxation, while manicured shrubs line the pathway leading to the front entrance.

Home in Centerville

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.

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Other great vacation rentals in Monticello

4.88 out of 5 average rating, 43 reviews

A tiny home is shown nestled in a natural setting, featuring a modern exterior with wooden siding and large windows. A spacious deck with a seating area welcomes guests, surrounded by lush greenery and a well-maintained lawn.

Tiny home in Thomasville

Thomasville's 1st Container Home

5 out of 5 average rating, 6 reviews

A living area is presented with two tan sofas, one featuring an attached ottoman. A flat-screen TV is mounted on the wall opposite, while a small side table holds a lamp. Light walls are complemented by a patterned area rug, and natural light filters through sheer curtains.

Home in Monticello

2-bedroom gem in Monticello.

A cozy bedroom features a spacious bed covered with a striped blanket, positioned near a decorative area rug. A minimalist artwork hangs above a fireplace, while dark curtains frame the windows, allowing natural light to gently illuminate the space.

4.82 out of 5 average rating, 74 reviews

Rest and Relax

The spacious kitchen features stainless steel appliances and ample cabinetry. A central wooden dining table with four chairs is positioned under a window, providing natural light. A classic fireplace adds character to the room, which has hardwood flooring and a neutral color palette.

5 out of 5 average rating, 19 reviews

Cottage 229 - Downtown Thomasville

A well-appointed kitchen features modern white cabinetry paired with warm wooden elements. Natural light streams through two windows, illuminating the marble countertop and creating a welcoming atmosphere. Open shelving displays decorative items, while a subtle area rug adds texture to the wooden floor.

5 out of 5 average rating, 13 reviews

Charber Farm Cabin

4.96 out of 5 average rating, 84 reviews

The kitchen area features modern cabinetry in a light gray hue, paired with a stainless steel refrigerator and stove. A microwave sits on the countertop, alongside a coffee maker. Natural light enters through a window above the sink, casting a bright ambiance.

Apartment in Levy Park

The Crooked Cottage

5 out of 5 average rating, 10 reviews

A well-appointed sleeping area features a spacious bed dressed in soft blue and cream bedding. Decorative pillows add texture against the headboard. Overhead cabinets provide storage, while a window allows natural light to fill the room, complemented by soft window treatments.

Camper/RV in Tallahassee

Misty Blue.