Vacation rentals in Jefferson County

A modern green exterior home is presented, featuring a symmetrical facade with large windows and a central front door. Neatly manicured landscaping includes shrubs and flower beds, all set against a backdrop of tall pine trees under a clear blue sky.

4.96 out of 5 average rating, 28 reviews

Walk to historic Monticello from this new home!

Newer home in historic Monticello! Fast and reliable wifi. Large master suite with private bath. Fully stocked kitchen with seating for 9. 58 in Smart TV. The outdoor screened in patio is a perfect spot to read a book. Very peaceful place to relax! A beautiful 25 mile drive to Tallahassee. Or take a walk and visit all the shops in Monticello. Great place to walk and ride bikes. Wacissa Springs is 19 miles and is a great place to enjoy time on a kayak. 23 miles to Thomasville. Clean & quiet!

Superhost

The exterior of a two-story home is showcased, featuring a large front porch with white railings and steps leading to the entrance. A white picket fence surrounds the property, and the design is complemented by lush greenery and trees nearby.

4.87 out of 5 average rating, 55 reviews

Charming 2 Bedroom 2 Bath , Private Cabana

Escape to our cozy, fully furnished 2-bedroom home with queen beds—yours to enjoy in complete privacy! Unwind on the screened porch with stunning views of North Florida’s pastures and rolling hills. Enjoy peace and comfort with private parking and entrance. Fully equipped for your stay, it's the perfect blend of relaxation and adventure. Just 9 miles east of Monticello and close to outdoor fun like hiking, kayaking, and more! Enjoy our lake views , it’s the perfect spot to unwind and recharge!

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.

Place to stay in Taylor County

A serene river landscape is captured, with tall trees lining the banks. The still water reflects the lush greenery above, creating a mirror-like effect. A clear blue sky is visible above, dotted with soft white clouds.

4.98 out of 5 average rating, 169 reviews

River Front Cottage Aucilla River, Taylor County

Furnished cottage with river view windows and a walk around deck. Open floor plan with king size bed and choice of either the full-size sleeper sofa or (2)comfy twin mattress beds . Enjoy relaxing and watch the river flow by from the swivel rocker recliner. Newly installed AC/Heating unit. Wall mounted swivel TV for easy viewing 200 channel Dish TV. Wi-Fi. The cottage is fully furnished, mini frig, microwave, toaster, coffee pot, dishware, bed and bath linens & basic cooking condiments.

4.94 out of 5 average rating, 48 reviews

A spa is featured beneath a wooden deck, with water swirling actively. Soft lighting adorns the overhead structure, and a flight of wooden stairs is visible in the background. Lush greenery surrounds the area, enhancing the serene atmosphere.

Guesthouse in Monticello

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.

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!

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.

5 out of 5 average rating, 9 reviews

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, 91 reviews

A spacious living area features large sliding glass doors that open to a wooden deck overlooking the surrounding woods. Natural light illuminates the room, which includes a comfortable seating arrangement and side tables. A ceiling fan and wall-mounted television are also present.

Cabin in Monticello

Fern Hollow Acres A peaceful retreat in the woods

Three bedroom lodge style house nestled in the woods in a retreat setting. Forget your worries in this spacious and serene space. Lovely grounds to walk around , enjoying deer, rabbits, owls and the occasional fox Butterfly, bees and bird sanctuary. Just 30 minutes to FSU/FAMU and the Florida Capitol. Twenty minutes to historic Monticello, Fl A short drive to the headwaters of the Wacissa River county park.with kayak and canoe rentals.

4.92 out of 5 average rating, 12 reviews

A cozy home is presented with a welcoming porch featuring wooden steps and a railing. The front yard is spacious, surrounded by lush greenery and mature trees. A bright blue sky complements the scene, highlighting the well-maintained exterior with metal roofing.

Home in Jefferson County

Sweet Southern Stay - pet friendly, fenced yard

Relax with the whole family! Located just 5 minutes from the interstate and 15 minutes from Tallahassee, this cozy home offers a perfect getaway from the hustle and bustle. Enjoy a serene setting with amenities that blend comfort with nature. Explore local attractions, historic downtown Monticello, or simply relax on the porch and enjoy the view. Book your stay now to experience the warmth and charm of this hidden gem!

The single-story home features a front porch, framed by shrubs and trees. A well-kept lawn surrounds the house, with pathways leading to the entrance. Flower beds add a touch of greenery, complementing the neutral exterior of the property.

4.96 out of 5 average rating, 51 reviews

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.

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.

5 out of 5 average rating, 62 reviews

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.

A comfortable living area features a light-colored sofa centered on a wood floor. Two lamps with dark bases and soft shades are positioned on either side on small tables. Soft light illuminates the space, enhancing the layout's inviting feel.