Vacation rentals in Jefferson County

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Top-rated vacation rentals in Jefferson County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost

A modern kitchen features sleek white cabinets paired with stainless steel appliances. A central island with seating for three is highlighted, and natural light enters through a window. Countertops are kept clear, enhancing the open feel of the space.

Home in Monticello

4.96 out of 5 average rating, 26 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!

Guest favorite

Cottage in Monticello

4.94 out of 5 average rating, 129 reviews

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.

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.

Home in Monticello

4.89 out of 5 average rating, 45 reviews

Private 2 Bedroom Cabana

Extra Spacey, Cozy and fully furnished second story 2 Bedroom Private home all to yourself. Spacious and light with an enclosed screened front porch Overlooking the beautiful pasture fruit trees and rolling hills of North Florida. . Private parking and entrance. All amenities to make your stay quiet and pleasant. We are 7 1/2 miles east of the town of Monticello and just a few minutes from kayaking and canoeing on the Wacissa River. 35 minutes to Tallahassee and 20min to Thomasville , GA

Top guest favorite

Two yellow chairs are positioned around a circular fire pit on a wooden deck, overlooking the calm river. The surrounding trees show hints of autumn colors, providing a natural backdrop for relaxation. The deck features railings that enhance safety while enjoying the scenic view.

Place to stay in Taylor County

4.97 out of 5 average rating, 153 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 comfy twin mattress bed . 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. The cottage is fully furnished, mini frig, microwave, toaster, coffee pot, dishware, bed and bath linens & basic cooking condiments.

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, 122 reviews

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!

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

4.88 out of 5 average rating, 17 reviews

Private Studio & Hot Tub on Gated Property!

Please read all check-in notes!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 & coffee shop, thrift and vintage stores as well as great dining in walking distance from property! Pet friendly! Message me for any questions!

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

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.

Guest favorite

A rustic cabin exterior is showcased with a metal roof and spacious porch. Wooden rocking chairs are arranged around a stone fire pit, surrounded by logs. Tall trees provide a natural backdrop and the area is framed by lush greenery.

Farm stay in Tallahassee

4.92 out of 5 average rating, 59 reviews

The Senator Cabin

Historic 19th century cabin updated with all the modern conveniences situated on the 210 acre Jubilee Blueberry Orchards property. Founded by Florida Legend Lawton Chiles, US Senator and Governor. Simply one-of-a-kind with fabulous floors, woodwork, claw tub and handcrafted shower. Breathtaking views all around and the only sounds are wind whispering through long leaf pines and live oaks. Plate glass window overlooking beautiful lake.

Superhost

A two-lane road stretches ahead, flanked by towering trees covered in moss. Sunlight filters through the branches, creating a dappled pattern on the asphalt. The vibrant greens of the foliage contrast with the warm tones of the road, offering a serene view of the surrounding nature.

Campsite in Tallahassee

5 out of 5 average rating, 3 reviews

Endless Adventures at Micco Campground!

Bring your own tent, RV and toys! Camp Micco is a privately owned, 7 acre parcel with a .25 acre cleared area for a campsite and/or RV parking. The rest is a wooded area that has a seasonal stream that flows through the center of the property. Only 28 minutes from the center of Tallahassee which includes a tranquil drive on Canopy Rd. Tent is not included. Unpaved roads leading up to property. There is no house on this property.

Guest favorite

A porch swing with a green and white leaf-patterned cushion is suspended from the ceiling, providing a comfortable seating option. Wooden decking surrounds the swing, with lush greenery visible in the background, framed by windows with green shutters.

Home in Jefferson County

4.9 out of 5 average rating, 10 reviews

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!

Guest favorite

An outdoor deck is featured with wooden flooring, surrounded by trees. Four metal chairs are arranged for seating, providing a space for outdoor relaxation. A doorway is visible leading into the interior of the home.

Home in Monticello

4.96 out of 5 average rating, 48 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.

Guest favorite

A practical kitchen space is visible, featuring white cabinetry and modern appliances, including a microwave and stove. Natural light filters in through a window, illuminating the countertop. A small rug lies in front of the sink, and decorative items are arranged on shelves.

Home in Monticello

4.95 out of 5 average rating, 61 reviews

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.