Vacation rentals in Monticello

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Top-rated vacation rentals in Monticello

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Guest favorite

Apartment in Tallahassee

4.98 out of 5 average rating, 167 reviews

Live Oak Cottages II InTown-Peaceful Retreat

Private long driveway to a quiet setting. Beautiful Live Oak trees around the grounds. It’s the upstairs cottage apartment with tall windows giving you a view to the Live Oak trees canopying together. The one by the cottage is 200 +years old!! Charming and cozy place to relax or work! Living room windows are tinted for privacy. Comfy bed and all the bedding is cleaned in between guests. There are plenty of towels, linens, and the essentials you need to be comfortable. Smart tv and Wifi too

Oct 13 – 20

G$21,155 GYD per night

Guest favorite

Cabin in Pavo

4.98 out of 5 average rating, 240 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

Oct 17 – 24

G$41,719 GYD per night

Guest favorite

Cottage in Monticello

4.96 out of 5 average rating, 112 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 25 – Apr 1

G$53,957 GYD per night

Guest favorite

Guesthouse in Tallahassee

4.83 out of 5 average rating, 253 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.

Jul 22 – 29

G$20,236 GYD per night

Guest favorite

Apartment in Monticello

4.86 out of 5 average rating, 21 reviews

Private 2 Bedroom Cabana

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

Jun 1 – 8

G$19,819 GYD per night

Guest favorite

Cottage in Thomasville

5.0 out of 5 average rating, 172 reviews

The Fern Leaf Cottage

Nestled in a residential neighborhood overlooking the owners beautifully designed and maintained garden is The Fern Leaf Cottage. You will have your own private drive to access the cottage. The Cottage is cozy and comfortable. Every detail is addressed and the decor will make you feel right at home. There is a small kitchenette furnished with a microwave, Keurig coffee maker, toaster, and small refrigerator. A great bonus is the little screened in porch complete with rocking chairs.

Feb 6 – 13

G$19,809 GYD per night

Guest favorite

Guest suite in Tallahassee

4.97 out of 5 average rating, 494 reviews

Home away from home Northside charmer suite

Lovely and completely renovated 1100 sqft in-law suite, fully self contained and private. It comes complete with a fully equipped kitchen (no commercial food preparation allowed) and bathroom with walk-in shower. Queen size bed in the bedroom, with a Queen size sleeper sofa in the living room. Has its own private entrances and dedicated driveway parking area, as well as self-check-in. No pets allowed. This is a strict non-smoking space, no smoking is allowed on the property.

May 22 – 29

G$17,913 GYD per night

Guest favorite

Cottage in Thomasville

4.97 out of 5 average rating, 345 reviews

The Shed-King Bed-Cozy-Modern Boho -Wifi-Cabin-

The Shed is located in a sprinkle of country, splash of city, Thomasville, GA. The Shed hosts a king bed and a combined kitchen living room space with a pullout Queen couch. You can spend your evenings outside on the patio with a fire or explore the beauty of historic downtown only 5 minutes away! A private 2 room guest house with a unique modern flare. No contact, keyless entry on arrival and a cozy, safe, clean space for your get away! We look forward to hosting you!

Jul 21 – 28

G$25,559 GYD per night

Guest favorite

Farm stay in Tallahassee

4.93 out of 5 average rating, 276 reviews

Goat House FarmStay Cottage - No Cleaning Fees!

Goat House Farm is a 501(c)3 nonprofit educational farm. All profits go toward supporting the mission of the farm. Come and de-stress by snuggling our goats. These bouncing bundles of joy are guaranteed to make you smile! We also have chickens, peacocks, honeybees, and even a pig. We are near Tallahassee but in a rural area, down a bumpy dirt road, but we promise the trip is worth it. Kayaking and hiking right off the property, plus beautiful sunsets on the lake.

Feb 26 – Mar 5

G$13,946 GYD per night

Guest favorite

Home in Quitman

4.95 out of 5 average rating, 251 reviews

small town living

Enjoy the laid back. simple, life of a small southern town. Our old house with hardwood floors, nice comfortable furniture, and vintage decorating choices is perfect for a leisurely get away or business. Great stay for travel nurses or others working temporarily in the area, or just a layover during travels. An air mattress and pack and play are also available. We do allow pets , a pet fee of 50.00 is charged under additional charges on the booking page.

Jun 23 – 30

G$21,666 GYD per night

Guest favorite

Home in Tallahassee

5.0 out of 5 average rating, 114 reviews

Sienna Lee Gardens: A Beautifully Renovated Home

Relax and unwind in this beautifully renovated 4 bedroom/3 bath home nestled on 20 acres of picture perfect live oaks, organic blueberry orchard, and abundant wildlife. There are so many places for entertaining including a large heated swimming pool (heated from March-Nov). There's a fully equipped kitchen, luxury beds and hotel quality linens. Every room has cable TV and internet throughout the house.

Jan 15 – 22

G$124,680 GYD per night

Guest favorite

Guesthouse in Taylor County

4.98 out of 5 average rating, 123 reviews

RiverRise Cottage on the Aucilla River

Furnished cottage with river view windows and a walk around deck. Open floor plan with king size bed and a full-size sleeper sofa. Enjoy relaxing and watch the river flow by from the swivel rocker recliner. AC/Heating unit. Wall mounted swivel TV for viewing 200 channel Dish TV, Wi-Fi is available. The cottage is fully furnished, mini frig, microwave, toaster, coffee pot, dishware, bed and bath linens.

Mar 19 – 26

G$27,136 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Monticello vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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

Home in Monticello

4.96 out of 5 average rating, 56 reviews

The Pearl Cottage - kid and pet friendly!

Mar 4 – 11

G$31,837 GYD per night

Guest favorite

Cabin in Monticello

4.97 out of 5 average rating, 62 reviews

Fern Hollow Acres A peaceful retreat in the woods

Feb 14 – 21

G$30,221 GYD per night

Guest favorite

Cottage in Monticello

4.9 out of 5 average rating, 89 reviews

The Knotted Oak Cottage- Fenced & Dog Friendly

Nov 13 – 20

G$36,160 GYD per night

Guest favorite

Cottage in Monticello

5.0 out of 5 average rating, 20 reviews

Peace, quiet & nature at the Dream House

Sep 13 – 20

G$17,959 GYD per night

Guest favorite

Guesthouse in Monticello

4.95 out of 5 average rating, 39 reviews

Cozy Country Cottage near Tallahassee

Jun 28 – Jul 5

G$26,119 GYD per night

Guest favorite

Home in Monticello

4.95 out of 5 average rating, 41 reviews

Home in Monticello near downtown w/ modern vibes

Aug 13 – 20

G$60,231 GYD per night

Guest favorite

Home in Monticello

5.0 out of 5 average rating, 19 reviews

Entire Brand New house in historic Monticello Fl

Sep 23 – 30

G$45,859 GYD per night

Superhost

Home in Monticello

4.83 out of 5 average rating, 12 reviews

Sunset Blue House - Secluded Pool Home on 4+ acres

Jun 21 – 28

G$101,950 GYD per night

Show all

Quick stats about vacation rentals in Monticello

Total rentals
20 properties
Rentals with dedicated workspaces
10 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
660 reviews
Nightly prices starting at
G$8,356 GYD 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 10 vacation rentals in Monticello featuring dedicated workspaces. Stay connected and productive in your home away from home.
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 bed and breakfast rentals in Monticello?
Experience the best of Monticello with our bed and breakfast rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget 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.

Vacation rentals in Monticello

Top-rated vacation rentals in Monticello

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Monticello vacation rentals

Stay near Monticello's top sights

Other great vacation rentals in Monticello

Home in Monticello

Cabin in Monticello

Cottage in Monticello

Cottage in Monticello

Guesthouse in Monticello

Home in Monticello

Home in Monticello

Home in Monticello

Quick stats about vacation rentals in Monticello

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Monticello?

Do bed and breakfast rentals in Monticello have wifi?

How much does it cost to stay in bed and breakfast rentals in Monticello?

Are there pet-friendly vacation rentals in Monticello?

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