Monticello vacation rentals

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Top-rated vacation rentals in Monticello

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

Guest favorite

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

Dec 6 – 13

R3,782 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

Guesthouse in Tallahassee

4.84 out of 5 average rating, 250 reviews

Beautiful Guest House in Desirable Northside

Hello and welcome to our home! This guest house is in our backyard and is very cozy with a large, private, screened-in porch. Sit in a rocking chair on the porch and enjoy the sounds of the many birds and the company of butterflies and hummingbirds. The King size bed is so comfortable! Our neighborhood lies between the Market District to the south and Bannerman Crossing to the North. There is shopping as well as many restaurants all around us. Downtown is 20 min away depending on traffic.

Sep 5 – 12

R1,834 ZAR per night

Popular amenities for Monticello vacation 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 vacation rentals in Monticello

Guest favorite

Townhouse in Tallahassee

4.94 out of 5 average rating, 120 reviews

Cheerful Easy Street Townhouse

Dec 10 – 17

R2,038 ZAR per night
Guest favorite

Guesthouse in Taylor County

4.98 out of 5 average rating, 121 reviews

RiverRise Cottage on the Aucilla River

Oct 1 – 8

R2,730 ZAR per night
Guest favorite

Home in Tallahassee

4.93 out of 5 average rating, 609 reviews

Eclectic Midtown home by Whole Foods near I-10

May 9 – 16

R1,940 ZAR per night
Guest favorite

Cottage in Thomasville

5.0 out of 5 average rating, 170 reviews

The Fern Leaf Cottage

Sep 30 – Oct 7

R1,796 ZAR per night
Guest favorite

Guest suite in Tallahassee

4.98 out of 5 average rating, 130 reviews

Bright, Modern Studio near Downtown & Universities

Apr 13 – 20

R1,601 ZAR per night
Guest favorite

Apartment in Tallahassee

4.88 out of 5 average rating, 512 reviews

COZY Studio Escape CLOSE-IN Kitchen Pool WRK-SPACE

Mar 20 – 27

R1,817 ZAR per night
Guest favorite

Apartment in Tallahassee

4.98 out of 5 average rating, 159 reviews

Live Oak Cottages II InTown-Peaceful Retreat

Aug 30 – Sep 6

R2,306 ZAR per night
Guest favorite

Townhouse in Tallahassee

4.98 out of 5 average rating, 302 reviews

Lovely in-town home away from home

Apr 4 – 11

R1,859 ZAR per night
Guest favorite

Home in Tallahassee

4.87 out of 5 average rating, 396 reviews

Mi Casa Su Casa

May 27 – Jun 3

R2,400 ZAR per night
Guest favorite

Home in Thomasville

4.97 out of 5 average rating, 208 reviews

Cozy Cottage Home in Historic Thomasville

Oct 23 – 30

R2,125 ZAR per night
Guest favorite

Townhouse in Tallahassee

4.87 out of 5 average rating, 198 reviews

The Elegant Sputnik - 2- Bedroom Downtown Home

Jun 14 – 21

R2,174 ZAR per night
Guest favorite

Apartment in Monticello

4.94 out of 5 average rating, 18 reviews

Private 2 Bedroom Cabana w/ Pool View

Apr 17 – 24

R1,796 ZAR per night

Other great vacation rentals in Monticello

Guest favorite

Cottage in Monticello

5.0 out of 5 average rating, 20 reviews

Peace, quiet & nature at the Dream House

Jul 5 – 12

R1,628 ZAR per night
Guest favorite

Home in Monticello

5.0 out of 5 average rating, 17 reviews

Entire Brand New house in historic Monticello Fl

May 7 – 14

R3,461 ZAR per night
Superhost

Home in Monticello

4.83 out of 5 average rating, 12 reviews

Sunset Blue House - Secluded Pool Home on 4+ acres

Apr 20 – 27

R9,241 ZAR per night
Guest favorite

Tiny home in Tallahassee

5.0 out of 5 average rating, 36 reviews

Cozy Country Cottage - Waterfront!

Nov 19 – 26

R2,012 ZAR per night
Guest favorite

Home in Thomasville

4.93 out of 5 average rating, 87 reviews

The Cottage at the Whinny Club

May 29 – Jun 5

R2,247 ZAR per night
Guest favorite

Home in Thomasville

4.96 out of 5 average rating, 25 reviews

Newly Renovated Thomasville Getaway Close to Town

Jul 23 – 30

R2,695 ZAR per night
Guest favorite

Home in Thomasville

4.98 out of 5 average rating, 91 reviews

Victoria Cottage -Walkable to Downtown

Jun 13 – 20

R2,249 ZAR per night
Guest favorite

Home in Thomasville

5.0 out of 5 average rating, 26 reviews

Spacious Home with Private Pool

Aug 4 – 11

R6,883 ZAR per night
Guest favorite

Cabin in Tallahassee

4.93 out of 5 average rating, 57 reviews

Coastal City Cabin: a Cute Florida Getaway Retreat

Nov 5 – 12

R3,919 ZAR per night
Guest favorite

Farm stay in Tallahassee

4.92 out of 5 average rating, 48 reviews

The Senator Cabin

Aug 11 – 18

R4,053 ZAR per night
Guest favorite

Home in Monticello

4.95 out of 5 average rating, 38 reviews

Home in Monticello near downtown w/ modern vibes

Jun 19 – 26

R5,460 ZAR per night
Guest favorite

Loft in Thomasville

5.0 out of 5 average rating, 35 reviews

The Jerger - Amazing loft in the heart of downtown

Feb 13 – 20

R7,722 ZAR per night

Quick stats about vacation 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

R757 ZAR before taxes and fees

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Monticello?

    Yes! Work meets play with ease at over 20 vacation rentals in Monticello featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Monticello?

    Four-legged friends are welcome in Monticello. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do bed and breakfast rentals in Monticello have wifi?

    Absolutely! We offer over 10 bed and breakfast rentals with wifi in Monticello. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Monticello?

    Experience the best of Monticello with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly vacation rentals in Monticello?

    Monticello has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Monticello have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Monticello. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

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