Vacation rentals in Jefferson County

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Top-rated vacation rentals in Jefferson County

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Guest favorite

Three individuals are seen kayaking on clear, turquoise waters surrounded by lush greenery. The tranquil setting features trees lining the riverbank, creating a serene atmosphere. The reflection of the foliage on the water adds to the peaceful ambiance of the scene.

Cottage in Monticello

4.94 out of 5 average rating, 129 reviews

The Cottage at Grand Oaks Plantation

LeviRating, 5 stars1 month ago

Amazing host!! Super friendly and truly amazing people!! So very relaxing especially with all the animals being around. The puppy dog Birdie gives great greatings and super nice hugs!!! We will definitely be back for a longer stay. Amazing little town with so cool antique shops and yummy restaurants!! The drive to Thomasville, Ga was short and that town was full of fun stuff to look at!!

A spacious home is surrounded by large oak trees, providing dappled sunlight on the ground. The porch features a welcoming area with seating, while the property extends into a lush green pasture, evoking a serene and tranquil outdoor setting.

Home in Monticello

4.89 out of 5 average rating, 45 reviews

Private 2 Bedroom Cabana

Ed At CASA TOARating, 5 stars1 month ago

Norman and Luise make your stay a pleasure. The farm is great, lots of things to do, as it accommodates to all sort of outdoors activities. You can go in the Cabana, or cottage, or RV, or even camping in the backcountry next to a beautiful lake. The vibe in the farm is always positive and you feel it the moment you go in. Norman can help you organize other activities or experiences in that beautiful area of Florida, 5 mins to Monticello, 30 to Tallahassee. A great place to stay!

Guest favorite

The exterior of the cottage is framed by large oak trees adorned with Spanish moss. A welcoming front porch features comfortable seating, while well-maintained bushes and plants create a pleasant entrance. The cottage's light-colored siding contributes to its charming appearance in the peaceful residential setting.

Cottage in Monticello

4.89 out of 5 average rating, 123 reviews

The Knotted Oak Cottage- Fenced & Dog Friendly

MeganRating, 5 stars6 days ago

The location was perfect for our fur babies that accompanied us on our trip, very cozy place and felt right at home! We appreciated the small details and the home had everything we needed during our stay! Will definitely recommend and book again to stay on our next trip to Monticello!

Top guest favorite

The exterior of a lodge-style house is presented, featuring wooden siding and large windows. A spacious covered porch with a railing is visible, surrounded by lush greenery. Sunlight filters through the trees, enhancing the natural setting of the home.

Cabin in Monticello

4.97 out of 5 average rating, 88 reviews

Fern Hollow Acres A peaceful retreat in the woods

HeleneRating, 5 stars5 days ago

We love staying at Cathy's home. Its clean, well stocked, child friendly and the property is very peaceful. Cathy is so accommodating. She is easy to contact if anything unexpected happens. This was our fourth stay. We have family close by so i plan our visits around Cathy's house availability. Thank you, Cathy for everything. We will definitely be back!

Superhost

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

4.89 out of 5 average rating, 19 reviews

Private Studio & Hot Tub on Gated Property!

LydiaRating, 5 stars5 days ago

It is a lovely setting. Other than the temperature issue with it being too warm and the thermostat not in the unit which was part of the description so we did know ahead of time but we couldn’t get ahold of her later when we needed it adjusted. In that situation someone should be available to monitor the only means of communication the customer has with you. But really everything else was beautiful, we used the little hot tub, and the bed was comfortable, and the kitchen had all we needed. The property is very beautiful.

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Popular amenities for Jefferson County vacation rentals

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Other great vacation rentals in Jefferson County

Top guest favorite

A spacious wrap-around porch is featured, adorned with rocking chairs and a dining set. Lush greenery and landscaped flower beds are visible beyond the railing, while the ceiling is painted in soft blue. Detailed architectural elements create a charming outdoor space.

Home in Monticello

5 out of 5 average rating, 40 reviews

The Bishop House est. 1909

LatonyaRating, 5 stars1 month ago

Enjoyed every last bit of our stay! They saved our weekend with having to book last minute and we enjoyed the whole weekend! Easy to get to, clear instructions and great recommendations for nearby restaurants! My family and I are very thankful for getting to experience this home!

A cozy living area features a comfortable couch and a small dining table positioned near large windows that allow natural light. A television is mounted on the wall, beside shelves with decorative items. The wooden floor adds warmth to the space.

Cottage in Monticello

4.74 out of 5 average rating, 23 reviews

Private Large 1 Bedroom Cottage

KristineRating, 5 stars3 weeks ago

It was a very nice, neat and clean 1 bedroom bungalow with plenty of room and more amenities than I needed for a two night stay. Nice bathroom & shower. Everything was in working order and comfortable. The arrival instructions were correct. The cell service is not great in the area. So using WiFi is helpful.

The exterior of the Budd-Pafford House is visible from above, showcasing its traditional architecture and expansive porch. Surrounded by lush gardens and mature trees, the house sits on a well-maintained lawn, leading to walkways that enhance the outdoor space.

Private room in Monticello

5 out of 5 average rating, 5 reviews

The Exploration Suite at The Budd-Pafford House

AnthonyRating, 5 stars7 months ago

The bed was super comfortable. We noticed that there were no toiletries in the bathroom. I messaged Barry and within 20 minutes had everything delivered to my door. Super nice vintage home. Easy to check in and out of. Pet friendly. I would rent again.

A corner of The Avera-Clarke House is visible, showcasing its classic yellow exterior and green-trimmed windows. Lush greenery surrounds the structure, enhancing the house's traditional charm. The roof features a gentle slope, and soft sunlight filters through the leaves, creating a serene atmosphere.

Private room in Monticello

5 out of 5 average rating, 3 reviews

Scarlett Room - At Avera-Clarke

LoyRating, 5 stars10 months ago

A great private room and the common areas were also clean and tidy. Brooke was super helpful and communicative. She also had great recommendations for food in town. Would stay again for sure!

Guest favorite