Holiday rentals in Monticello

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Top-rated holiday rentals in Monticello

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

Guest favourite

Cabin in Pavo

4.97 out of 5 average rating, 233 reviews

Cabin on Lake Nichols

Enjoy a comfortable retreat in a historic 1930s cabin overlooking a 350-acre private lake. This fully renovated farmhouse features its original beadboard. The historic touches, combined with all the modern amenities, make this the perfect destination for those seeking to enjoy a getaway into nature and fishing experience. The lake is loaded with largemouth bass, catfish, speckled perch, bream, and bluegill and is only otherwise available by very limited membership. See more on IG @lake_nichols

6–13 Dec

$269 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.

6–13 Aug

$353 SGD per night
Guest favourite

Farm stay in Hahira

5.0 out of 5 average rating, 151 reviews

The Silo at Oak Hill Farm~romantic outdoor bath

The Silo at Oak Hill Farm is located on a multi-generational Centennial family farm in rural South Georgia. Overlooking beautiful pastureland 5 miles from interstate 75, this converted grain silo is a perfect getaway for those who enjoy a farm setting. Designed with a modern farmhouse feel, it has all of the amenities of home with a little twist. *Please read about extra amenities/concierge services in “The Space” section* Come enjoy southern hospitality in a one of a kind overnight experience.

4–11 Feb

$205 SGD per night

Popular amenities for Monticello holiday rentals

Stay near Monticello's top sights

Rev Cafe11 locals recommend
Tupelo's Bakery & Cafe7 locals recommend
Monticello Opera House, Inc.8 locals recommend

Other great holiday rentals in Monticello

Guest favourite

Home in Thomasville

4.99 out of 5 average rating, 192 reviews

Executive Suite on Park Ave.

6–13 Jan

$178 SGD per night
Guest favourite

Townhouse in Tallahassee

4.87 out of 5 average rating, 198 reviews

The Elegant Sputnik - 2- Bedroom Downtown Home

1–8 Apr

$123 SGD per night
Guest favourite

Townhouse in Tallahassee

4.94 out of 5 average rating, 120 reviews

Cheerful Easy Street Townhouse

9–16 Jun

$145 SGD per night
Guest favourite

Townhouse in Tallahassee

4.98 out of 5 average rating, 303 reviews

Lovely east side home away from home.

13–20 Apr

$147 SGD per night
Guest favourite

Guest house in Taylor County

4.98 out of 5 average rating, 121 reviews

RiverRise Cottage on the Aucilla River

6–13 Mar

$195 SGD per night
Guest favourite

Flat in Monticello

4.94 out of 5 average rating, 18 reviews

Private 2 Bedroom Cabana w/ Pool View

20–27 Mar

$128 SGD per night
Guest favourite

Guest house in Monticello

4.94 out of 5 average rating, 36 reviews

Cozy Country Cottage near Tallahassee

1–8 Jun

$169 SGD per night
Guest favourite

Home in Monticello

4.96 out of 5 average rating, 54 reviews

The Pearl Cottage - kid and pet friendly!

5–12 Oct

$206 SGD per night
Guest favourite

Cabin in Monticello

4.97 out of 5 average rating, 60 reviews

Fern Hollow Acres A peaceful retreat in the woods

31 Dec – 7 Jan

$195 SGD per night
Guest favourite

Cottage in Monticello

4.9 out of 5 average rating, 88 reviews

The Knotted Oak Cottage- Fenced & Dog Friendly

7–14 Nov

$234 SGD per night
Guest favourite

Cottage in Monticello

5.0 out of 5 average rating, 20 reviews

Peace, quiet & nature at the Dream House

6–13 Jul

$116 SGD per night
Guest favourite

Home in Monticello

5.0 out of 5 average rating, 17 reviews

Entire Brand New house in historic Monticello Fl

15–22 Jun

$274 SGD per night

Quick stats about holiday rentals in Monticello

Total rentals

30 properties

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

650 reviews

Nightly prices starting at

$54 SGD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Jefferson County
  5. Monticello