Ferienunterkünfte mit Sitzbereich im Freien in Jefferson County

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!

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.

Sunset Blue House - Secluded Pool Home on 4+ acres

Located on the outskirts of Monticello Florida, this home boasts over 2800 ft including an in-ground pool. With plenty of space for outdoor and indoor activities; this property is equipped with basketball and volleyball areas, fitness/gaming area, and office. This 3 bedroom/3 bathroom sits on 4.31 acres so, there is plenty of room to spread out or come together. Just in time for this year's football season; FSU, FAMU, and TCC are less than 25 mins away. Book now as it won't not last long!

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!

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.

Private Studio & Hot Tub on Gated Property!

No Cleaning fees! Private & Safe! Escape from the daily grind or traveling. Near an i10 exit: 2 exits East of Florida's Capitol. Located in a Historic Downtown area featuring large ole Southern homes — famous for ghost tours! Enjoy live music on Friday nights, Wed. open market, wkend live theatre, antique shopping, great cafés & coffe, thrift and vintage stores as well as great dining in walking distance from property! Pet friendly! You won't regret booking!😁

Bogetti Family Farm

Relax with the whole family at this peaceful farm. Enjoy a rest on the front porch or go for a hike around and explore the trails. Schedule an in house massage. Say hello to the friendly goats. Enjoy a day trip to the Gulf or one of the many blue springs of North Florida. 23 miles to Keaton beach, 5 miles to Walmart/Winn-Dixie, and 4 miles to shopping in historic downtown Perry. Plenty of room to park your boat

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.

The Pearl Cottage - kid and pet friendly!

Relax with the whole family, well behaved dogs and cats included! The Pearl Cottage is located on a peaceful and charming street in downtown Monticello. A park with a playground is only a couple blocks away. Eat and shop local for the day. Tallahassee is 30 minutes away, Alligator Point is 1hr 20 minutes.