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.

Guest favorite

Cottage in Monticello

5.0 out of 5 average rating, 20 reviews

Peace, quiet & nature at the Dream House

Min. 2 nt. stay at very large property. 3 mi. from the Wacissa, a freshwater spring of first magnitude, canoe & swim. Our quirky Dream House is est. 550 sq. ft. Want perfect & sterile? That's not us! :) Live Oaks\Spanish Moss. One mile on a slightly bumpy, rutted, private dirt road. One behaved dog OK, cleaning charge for doggie extra. Lake but water naturally drained winter 2023. Owls, heron, quail, deer at dusk and dawn; turkey. Plenty of hiking. See the stars. Find peace, no humans but you!

Jul 5 – 12

R1,628 ZAR per night
Guest favorite

Cottage in Monticello

4.96 out of 5 average rating, 110 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.

Mar 22 – 29

R4,960 ZAR per night
Guest favorite

Apartment in Monticello

4.94 out of 5 average rating, 18 reviews

Private 2 Bedroom Cabana w/ Pool View

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 4 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

Apr 17 – 24

R1,796 ZAR per night

Popular amenities for Jefferson County vacation rentals

Other great vacation rentals in Jefferson County

Guest favorite

Home in Monticello

4.95 out of 5 average rating, 39 reviews

Charming cottage located on a historic street.

Nov 21 – 28

R2,516 ZAR per night

Home in Monticello

4.74 out of 5 average rating, 35 reviews

The Monticello Getaway

Jul 13 – 20

R2,462 ZAR per night

Home in Monticello

4.68 out of 5 average rating, 28 reviews

Country Pool House-Perfect for families, private

May 9 – 16

R2,654 ZAR per night

Farm stay in Monticello

4.58 out of 5 average rating, 12 reviews

Hunter's Run Wildlife Area (Dog Friendly)

Mar 7 – 14

R3,782 ZAR per night
Guest favorite

Bed and breakfast in Monticello

4.9 out of 5 average rating, 83 reviews

Carriage House 1897

Jul 23 – 30

R3,598 ZAR per night
Guest favorite

Camper/RV in Monticello

5.0 out of 5 average rating, 8 reviews

Mini Moo Alpaca Too Farm

Nov 3 – 10

R3,253 ZAR per night
Guest favorite

Guesthouse in Monticello

5.0 out of 5 average rating, 9 reviews

2 Bedroom/2 Bath Cottage close to Tallahassee

Oct 8 – 15

R4,402 ZAR per night

Condo in Taylor County

5.0 out of 5 average rating, 5 reviews

Lovely 2-bedroom condo with pool and river access

Oct 22 – 29

R2,798 ZAR per night
Guest favorite

Home in Monticello

4.88 out of 5 average rating, 8 reviews

Lagniappe, Get a little extra!

May 30 – Jun 6

R3,535 ZAR per night

Barn in Monticello

5.0 out of 5 average rating, 3 reviews

Quiet country cottage.

Nov 12 – 19

R1,459 ZAR per night
Guest favorite

Home in Monticello

5.0 out of 5 average rating, 30 reviews

2 Bedroom Bungalow in Historic Monticello FL

Feb 3 – 10

R2,954 ZAR per night

Tiny home in Monticello

4.75 out of 5 average rating, 8 reviews

Downtown Monticello Teeny House

Jan 13 – 20

R1,426 ZAR per night