Holiday rentals in Jefferson County

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Jefferson County

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

Guest favourite

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!

5–12 Jul

$116 SGD per night
Guest favourite

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.

22–29 Mar

$353 SGD per night
Guest favourite

Flat 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

17–24 Apr

$128 SGD per night

Popular amenities for Jefferson County holiday rentals

Other great holiday rentals in Jefferson County

Guest favourite

Home in Monticello

4.95 out of 5 average rating, 39 reviews

Charming cottage located on a historic street.

21–28 Nov

$179 SGD per night

Home in Monticello

4.74 out of 5 average rating, 35 reviews

The Monticello Getaway

13–20 Jul

$175 SGD per night

Home in Monticello

4.68 out of 5 average rating, 28 reviews

Country Pool House-Perfect for families, private

9–16 May

$189 SGD per night

Farm stay in Monticello

4.58 out of 5 average rating, 12 reviews

Hunter's Run Wildlife Area (Dog Friendly)

7–14 Mar

$269 SGD per night
Guest favourite

Bed and breakfast in Monticello

4.9 out of 5 average rating, 83 reviews

Carriage House 1897

23–30 Jul

$256 SGD per night
Guest favourite

Campervan/Motorhome in Monticello

5.0 out of 5 average rating, 8 reviews

Mini Moo Alpaca Too Farm

3–10 Nov

$231 SGD per night
Guest favourite

Guest house in Monticello

5.0 out of 5 average rating, 9 reviews

2 Bedroom/2 Bath Cottage close to Tallahassee

8–15 Oct

$313 SGD per night

Apartment in Taylor County

5.0 out of 5 average rating, 5 reviews

Lovely 2-bedroom condo with pool and river access

22–29 Oct

$199 SGD per night
Guest favourite

Home in Monticello

4.88 out of 5 average rating, 8 reviews

Lagniappe, Get a little extra!

30 May – 6 Jun

$252 SGD per night

Barn in Monticello

5.0 out of 5 average rating, 3 reviews

Quiet country cottage.

12–19 Nov

$104 SGD per night
Guest favourite

Home in Monticello

5.0 out of 5 average rating, 30 reviews

2 Bedroom Bungalow in Historic Monticello FL

3–10 Feb

$210 SGD per night

Tiny home in Monticello

4.75 out of 5 average rating, 8 reviews

Downtown Monticello Teeny House

13–20 Jan

$102 SGD per night