Vacation rentals in Jefferson County

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!

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.

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.

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.

Spring Warrior Pines

Plenty of land for boats and vehicles. Use the cleaning station for all your hunting and fishing trips. A fire pit to enjoy the night air. Swings for the kids & for the adult kids is corn hole, checkers & horseshoe games. Furry friends are welcome and have their own suite, if needed. (fee is $30 per pet)The perimeter is fenced. We have a Baby crib and Highchair for our littlest friends. Gas and charcoal grill is available, bring the charcoal!

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!

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.