Vacation rentals in Jefferson County

A newer home features a vibrant green exterior complemented by white accents. Windows are framed with clean lines, and a welcoming porch is visible. Surrounding the house, a well-maintained lawn adds to the inviting appearance, with trees in the background providing shade.

4.96 out of 5 average rating, 27 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!

Place to stay in Taylor County

A serene river scene captures several turtles basking on a fallen log. The calm water reflects the surrounding natural foliage, with bare branches and green plants framing the view. This tranquil setting highlights the local wildlife that can often be observed from the cottage.

4.98 out of 5 average rating, 162 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. Fiber Optic 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, 130 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.

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

4.91 out of 5 average rating, 34 reviews

Guest house, Hot tub & King Bed on Gated Property!

Please read all check-in notes! 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

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!

4.96 out of 5 average rating, 25 reviews

A wooden bench faces a spacious swing set situated in a wooded area. Tall pine trees surround the space, with leaves scattered on the ground. Bird feeders are mounted on nearby trees, enhancing the serene outdoor setting.

Home in Perry

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!

4.97 out of 5 average rating, 89 reviews

A dining area is displayed with a large wooden table surrounded by several chairs, set against a backdrop of natural light from a window with a diamond pattern. Wooden beams and a door leading outside provide an inviting and spacious atmosphere.

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.

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

Tally Woods Retreat- 7 Acres with a stream!

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.

4.91 out of 5 average rating, 11 reviews

Three wall-mounted dispensers are arranged side by side, each containing a different product. Labels indicate 'Shampoo,' 'Conditioner,' and 'Body Soap.' The dispensers are sleek in design, featuring clear containers that allow visibility of the contents inside.

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!

A laundry area features a washer and dryer, both in white, positioned side by side. Above, a wire shelf holds various laundry supplies, including bottles of detergent. A fire extinguisher is mounted on the wall, ensuring safety in this functional space.

4.96 out of 5 average rating, 50 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.

A compact bathroom is shown, featuring a sleek, white sink with a mirror above. Soft lighting from three fixtures illuminates the space, while light gray walls and beige tiled flooring create a subtle contrast. A toilet and a decorative shelf with toiletries are also visible.

4.95 out of 5 average rating, 64 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.

4.87 out of 5 average rating, 152 reviews

A spacious living area is surrounded by large sliding glass doors, offering views of the river and lush greenery outside. A wooden entertainment unit and comfortable seating options, including a recliner and rocking chairs, are visible, creating an inviting space filled with natural light.

Home in Taylor County

Nature Lover's Aucilla River Beauty

Moorings at Mandalay is ultimate, unique eco-tourist destination; a true nature lover’s paradise inside the St. Marks National Wildlife Refuge on the Aucilla River; birding, boating, canoeing, hiking, hunting, scalloping, fishing, and photography. Pets are allowed with a $50 pet fee per animal and modern flea protection-contact owner when booking.

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Popular amenities for Jefferson County vacation rentals

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Other great vacation rentals in Jefferson County

A rustic guest house is nestled beside a serene pond, framed by lush greenery. The wooden structure features a metal roof and a welcoming porch with seating. Tall grass sways gently in the foreground, enhancing the natural setting of the property.

Cottage in Perry

4.71 out of 5 average rating, 24 reviews

Little Fish House (Casita de Peces)

VanessaRating, 5 stars16 months ago

a great stay! Kenneth was super responsive whenever I had any questions. AMAZING value for the price. there's also animals on he property! very cute cows and friendly donkeys that come right up to the fence to say hi :) the entire property is fenced and if you have larger animals is a great place for them to get their energy out. definitely worth the price!

A stone fire pit surrounded by brick paving showcases a vibrant fire, with flames rising from a stack of logs. Wooden chairs are positioned nearby, allowing for gathering and conversation. Trees stand in the background, complementing the natural setting.

4.88 out of 5 average rating, 100 reviews

The Blue Room at Pedro's Perch

VioletaRating, 5 stars1 month ago

the Perch of Pedro is a great place to stay in middle of nature it is peaceful full of threes and beautiful garden.

The exterior of a two-bedroom home is displayed, featuring a sloped roof and a combination of large windows. Lush green landscaping and trees surround the property, providing a natural ambiance. A gravel path leads to the entrance, enhancing the secluded feel.

Home in Jefferson County

Smiling Farms Retreat

EricRating, 5 stars6 months ago

Very peaceful piece of property surrounded by farms. Comfortable home. Easy layout, great outside space, large deck, with Jacuzzi. Pretty country ride to the home. About a 30 minute ride to the quaint town of Monticello. Easily worth the trip. Try Tupelos bakery for the best cup of coffee!

A gravel driveway leads to a gated entrance. The gate is surrounded by lush greenery and tall trees, with a clear sky visible in the background. A black fence lines the property, adding to the serene and rural setting.

5 out of 5 average rating, 40 reviews

Two Beard Farm (Bunk house)

JasonRating, 5 stars2 weeks ago

Loved the place, peaceful and cozy, exactly what I wanted for the kids

A back porch is sheltered by a roof and features a cozy seating area with two wicker chairs, a floral-covered sofa, and soft cushions. A small table and a potted plant add a touch of greenery, while natural light filters through windows of the house beyond.

4.97 out of 5 average rating, 69 reviews

The Strawbridge Place

TammyRating, 5 stars3 weeks ago

Michael and the girls( her pups) greated us. Very friendly dogs and their mom to. She told us everything we wanted to know about the town..Gave us a quick History lesson about some people who lived in Monticello. Easy to talk to and eager to please with anything. The room was perfect, super clean, beautifully decorated, small fridge for cooler items, coffee,fruit and breakfast snack bars also. Sleeping was completely quiet..heard nothing all night..I can't say enough about her, she was very kind, and socialable. Our goal is to move to the area and she hooked us up with a realtor that's helping us. Thanks Michaele for everything..!!

A view of the vibrant downtown street reveals a mix of shops and eateries across the way. Two parked vehicles are visible, alongside a planter filled with greenery. Striped awnings provide shade, and a clear blue sky with scattered clouds adds to the scene.

4.88 out of 5 average rating, 32 reviews

Luxe-Historic Suite in Downtown Monticello

RebeccaRating, 5 stars1 month ago

Clean, spacious room, choice of coffee or tea was great for the mornings. The bed was comfortable. The price was very reasonable for graduation weekend at FSU. Would recommend for a weekend place to stay during Tallahassee events or when traveling in the local area.

A screened lanai is presented, featuring a concrete floor and metal framework. Two kayaks in green and orange are positioned on the left, while a white door leads outside on the right. Natural light filters in through the screens, showcasing the surrounding greenery.

Camper/RV in Perry

Coastal Hideaway

OliviaRating, 5 stars11 months ago

Perfect spot for our camper and no problems with anything else. And the screen room is great!!!

A clean and functional bathroom setting features a white toilet adorned with neatly stacked terracotta towels. A silver toilet paper holder and a small wastebasket can be seen nearby, with gray walls and white trim providing a subtle backdrop.