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Vacation rentals in Monticello

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Top-rated vacation rentals in Monticello

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

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Cabin in Pavo

4.97 out of 5 average rating, 267 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

Cottage in Monticello

4.93 out of 5 average rating, 123 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.

Guesthouse in Tallahassee

4.85 out of 5 average rating, 280 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, 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 and FSU are 20 min away depending on traffic.

Cabin in Tallahassee

4.95 out of 5 average rating, 130 reviews

Coastal City Cabin: A Cozy Florida Getaway A-Frame

Picture this.. Spend the day fishing out on the coast or swimming in the world's largest freshwater spring then some fun in town with great eats & live music! Finish the night with a hot tub soak under the stars. No worries, you can do it all again tomorrow! Conveniently nestled between Tallahassee and the 'Forgotten Coast', our cabin is a perfect match for your adventure-filled vacation. A quick 15 minute ride from the Tallahassee airport has you enjoying the sunset from our rocking chairs.

Cottage in Thomasville

5 out of 5 average rating, 186 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.

Guesthouse in Tallahassee

4.94 out of 5 average rating, 219 reviews

The Carriage House

Our lovely French inspired guest house features an open floor plan, 12-foot ceilings with real wood beams, a fully equipped kitchen and large brick patio overlooking a spacious backyard with shared pool. The two bedrooms are connected by a jack and jill bathroom featuring a tub/shower combination. the second bathroom, located just down the hall, has a standup shower. For additional guests, there are more sleeping arrangements in the family room on a single bed pullout love seat.

Place to stay in Taylor County

4.97 out of 5 average rating, 141 reviews

River Front Cottage Aucilla River, Taylor County

Furnished cottage with river view windows and a walk around deck. Open floor plan with king size bed and choice of either the full-size sleeper sofa or comfy twin mattress bed . Enjoy relaxing and watch the river flow by from the swivel rocker recliner. Newly installed AC/Heating unit. Wall mounted swivel TV for easy viewing 200 channel Dish TV. The cottage is fully furnished, mini frig, microwave, toaster, coffee pot, dishware, bed and bath linens & basic cooking condiments.

Cottage in Monticello

4.91 out of 5 average rating, 111 reviews

The Knotted Oak Cottage- Fenced & Dog Friendly

Enjoy this cozy “dog friendly” 2 BR cottage on a quiet residential street in the heart of Monticello’s historic district. This cottage is an easy walk to downtown and is ideal for couples or friends for a relaxed getaway. Well-behaved potty trained dogs ( max 2) are welcome! The cottage has a fenced in yard and is located on a perfect street for dog walking. The cottage front porch is the perfect place to unwind with a cocktail before walking to dinner. On Instagram too!

Cottage in Thomasville

4.96 out of 5 average rating, 392 reviews

The Shed-King Bed-Cozy-Modern Boho - Grand Piano

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!

Home in Quitman

4.95 out of 5 average rating, 288 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.

Home in Tallahassee

4.95 out of 5 average rating, 147 reviews

Vickie's Hideway

Hideaway says it all, Located in a peaceful beautiful country setting. You have 1 acre to sit back, relax, and enjoy what Mother nature has to offer and just a short drive back to Tallahassee for all the amenities of the city. Nearest Walmart - 8 miles Capital Regional Hospital (CRMC) - 12 miles Tallahassee Memorial Hospital - 13 miles Tallahassee Regional Airport - 17 miles Donald Tucker Civic Center - 12 miles Doak Campbell Stadium - 13 miles

Home in Tallahassee

5 out of 5 average rating, 129 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.

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Popular amenities for Monticello vacation rentals

Free parking on premises

Air conditioning

Stay near Monticello's top sights

Rev Cafe11 locals recommend

Monticello Opera House, Inc.8 locals recommend

Tupelo's Bakery & Cafe7 locals recommend

Other great vacation rentals in Monticello

Farm stay in Cairo

4.96 out of 5 average rating, 49 reviews

Katahdin Cottage @ Loblolly Lamb Farm

Home in Alligator Point

5 out of 5 average rating, 29 reviews

Tucked Away Private Beachfront Home

Cabin in Boston

5 out of 5 average rating, 47 reviews

Cozy cabin in the Georgia pines! Retriever kennels

Home in Tallahassee

4.81 out of 5 average rating, 42 reviews

Town & Country Getaway

Home in Monticello

4.88 out of 5 average rating, 17 reviews

Sunset Blue House - Secluded Pool Home on 4+ acres

Tiny home in Tallahassee

4.94 out of 5 average rating, 52 reviews

Gardenview Tiny House

Tiny home in Tallahassee

5 out of 5 average rating, 57 reviews

Cozy Country Cottage - Waterfront!

Home in Berlin

4.96 out of 5 average rating, 47 reviews

Western Home in the Heart of Berlin, Georgia

Quick stats about vacation rentals in Monticello

Total rentals
20 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
710 reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi

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 $130 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.

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