Holiday rentals in Jefferson County
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Top-rated holiday rentals in Jefferson County
Guests agree: these stays are highly rated for location, cleanliness and more.
Cottage in Monticello
5.0 out of 5 average rating, 20 reviewsPeace, 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!
5–12 Jul
Cottage in Monticello
4.96 out of 5 average rating, 110 reviewsThe 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.
22–29 Mar
Flat in Monticello
4.94 out of 5 average rating, 18 reviewsPrivate 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
17–24 Apr
Holiday rentals for every style
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Popular amenities for Jefferson County holiday rentals
Other great holiday rentals in Jefferson County
Home in Monticello
4.95 out of 5 average rating, 39 reviewsCharming cottage located on a historic street.
21–28 Nov
Home in Monticello
4.74 out of 5 average rating, 35 reviewsThe Monticello Getaway
13–20 Jul
Home in Monticello
4.68 out of 5 average rating, 28 reviewsCountry Pool House-Perfect for families, private
9–16 May
Farm stay in Monticello
4.58 out of 5 average rating, 12 reviewsHunter's Run Wildlife Area (Dog Friendly)
7–14 Mar
Bed and breakfast in Monticello
4.9 out of 5 average rating, 83 reviewsCarriage House 1897
23–30 Jul
Campervan/Motorhome in Monticello
5.0 out of 5 average rating, 8 reviewsMini Moo Alpaca Too Farm
3–10 Nov
Guest house in Monticello
5.0 out of 5 average rating, 9 reviews2 Bedroom/2 Bath Cottage close to Tallahassee
8–15 Oct
Apartment in Taylor County
5.0 out of 5 average rating, 5 reviewsLovely 2-bedroom condo with pool and river access
22–29 Oct
Home in Monticello
4.88 out of 5 average rating, 8 reviewsLagniappe, Get a little extra!
30 May – 6 Jun
Barn in Monticello
5.0 out of 5 average rating, 3 reviewsQuiet country cottage.
12–19 Nov
Home in Monticello
5.0 out of 5 average rating, 30 reviews2 Bedroom Bungalow in Historic Monticello FL
3–10 Feb
Tiny home in Monticello
4.75 out of 5 average rating, 8 reviewsDowntown Monticello Teeny House
13–20 Jan
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