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Holiday houses in Monticello

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Quick stats about holiday rentals in Monticello

  • Total holiday rentals

    Explore 30 holiday rentals in Monticello

  • Nightly prices starting at

    Monticello holiday rentals start at $57 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,200 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Monticello holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Monticello rentals

  • 4.9 Average rating

    Monticello stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated holiday rentals in Monticello

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

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Top Guest favourite
The entrance features a charming pathway lined with carefully arranged stones, leading to a welcoming porch adorned with white wooden doors. Lush greenery and shrubs frame the space, providing a serene atmosphere, while the screened-in porch invites relaxation under the surrounding trees.
Cottage in Monticello
4.95 out of 5 average rating, 150 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.

LocationValueBathroom

Top Guest favourite
The guest house is nestled in a lush green setting, featuring a large screened-in porch illuminated by soft outdoor lighting. The exterior displays a blend of dark wood and light accents, with a welcoming entrance door and surrounded by well-maintained garden space.
Guesthouse in Tallahassee
4.87 out of 5 average rating, 384 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.

ValueFamilyLayout

Top Guest favourite
A cozy room features a spacious bed dressed in colorful bedding, accompanied by decorative pillows. A vintage chair sits nearby, complementing the natural wood wall. Sunlight filters gently through the curtains, while a mirror reflects the inviting atmosphere of the space.
Tiny home in Tallahassee
4.99 out of 5 average rating, 103 reviews

Cozy Country Cottage - Waterfront!

Enjoy the sounds of nature when you stay in this unique country cottage on private Turkey Pond. Deer, turkey & raptors are just some of the wildlife you may encounter. Stunning sunsets are common & kayaks are on hand for a paddle. There is outdoor seating & a sun umbrella for the porch and stars twinkle on clear nights. Special touches make your stay comfy & cozy including on-demand hot water, a luxurious queen bed w/ a cozy comforter, mini-split heat/ac, dish network, smart tv & much more.

LocationFamilyTV

Guest favourite
A welcoming entrance features a white wooden facade with a classic porch. Two rocking chairs sit on a brick pathway leading to a front door adorned with a wreath. Sunlight filters through nearby trees, creating a serene outdoor atmosphere.
Home in Thomasville
4.94 out of 5 average rating, 200 reviews

Edgewood Cottage

Whether you're in town for an event or looking for a getaway, you'll feel cozy, comfortable, and right at home in this historic cottage. Built in 1916, the home offers historic charm and modern amenities. With more than 1,600 sq. ft. and three bedrooms, there's room for the whole family! There's a huge fenced-in yard and Macintyre Park is just half a block away. The front porch and back deck offer serenity under the pines. Or take a 3 minute drive to experience all that downtown has to offer.

ValueLocationWalkability

Guest favourite
A spa is featured beneath a wooden deck, with water swirling actively. Soft lighting adorns the overhead structure, and a flight of wooden stairs is visible in the background. Lush greenery surrounds the area, enhancing the serene atmosphere.
Guesthouse in Monticello
4.92 out of 5 average rating, 113 reviews

Private Hot tub, Adjusting Kingbed, Gated Property

Read All to get Pet Discount! Walk to Historic District: famous for Ghost Tours, Good eats, Antique shopping, Live theatre, and Music on Fri. Nite @ THE Social. Returning Guests - before booking, send an "inquiry" for 50% Less Pet Fee! Also applies to "One Nite" booking with Pet! - Please Be Sure To Add Pets & Any Guest with you Upon Booking (list service animals as guest for insurance purposes). Pet fees are per stay, not per nite. - Any Smoking: Outside Only! [Medical also outside Only].

ValueLocationKitchen

Top Guest favourite
A wooden cabin with a screened porch is set in a lush green landscape. Surrounding trees provide dappled shade, while colorful flowering plants enhance the serene atmosphere. The cabin features a metal roof and is partially obscured by greenery, emphasizing the secluded environment.
Cabin in Tallahassee
5 out of 5 average rating, 184 reviews

Twisted Pine Lake Cabin, secluded & near town

Close to everything, a million miles away....... Down the two-track driveway, past the view of the nearest neighbors, our new custom cabin awaits. Rest easy on the screened porch, with its view of the two-acre lake or cross the adjacent foot bridge to the island. Fish for bass and bream, stroll the walking path, paddle around and enjoy the wildlife, or just relax far from the madding crowd. This slice of paradise sits on 12 acres; our home is across the lake, out of sight and out of mind.

FamilyLocationCondition

Top Guest favourite
The exterior of a charming two-bedroom home features a light blue façade with white accents. A covered entryway provides shelter, while a stone pathway leads to the porch. Lush green grass surrounds the house, complemented by landscaping and a tree offering shade.
Home in Monticello
4.97 out of 5 average rating, 30 reviews

Welcome to The Schoolhouse

This special place is close to everything, making it easy to plan your visit. Discover this fully renovated 1926 two-bedroom gem in the heart of Monticello, Florida. Named for one of two schoolhouses originally associated with the church now housing Monticello’s Chamber of Commerce, the home still reflects its history. From reclaimed hardwood floors to refurbished original windows, doors, and moldings, you can experience the best of modern amenities and historic charm.

LocationValueCheck-in

Top Guest favourite
A single-story home is positioned beside a two-car garage, both surrounded by well-maintained grass. Tall trees form a backdrop, providing a sense of privacy and tranquility. The house features multiple windows and a small set of steps leading to the entrance.
Home in Tallahassee
4.96 out of 5 average rating, 187 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

LocationFamilyCheck-in

Top Guest favourite
The entrance features a stylish door framed by lush greenery and elegant planters. Clear glass panes allow natural light to illuminate the entryway, enhancing the welcoming atmosphere. The semi-gloss finish of the door contrasts gently with the natural wood siding.
Home in Thomasville
4.99 out of 5 average rating, 254 reviews

Executive Suite on Park Ave.

FREE, FREE FREE RENT TWO NIGHTS AND THE THIRD NIGHT IS TOTALLY FREE. JULY AND AUGUST This is the most elegant and tranquil 1250 Sq ft. of pure comfort! It features a library quiet central smart H & A. system (not a window air) can be set to 70 in the summer and 68 in the winter. Large one bedroom with a Tempur-pedic luxury king size bed . 7 ft glass shower . Sofa can be used as an Extra long twin. Full kitchen with dishwasher

ValueLocationAmenities

Top Guest favourite
The charming exterior of the home is framed by large live oak trees, providing shade and a serene setting. A wide porch, bordered by white railings, invites relaxation, while manicured shrubs line the pathway leading to the front entrance.
Home in Tallahassee
5 out of 5 average rating, 169 reviews

Sienna Lee Gardens: A Beautifully Renovated Home

Relax and unwind in this beautiful 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 swimming pool. There's a fully equipped kitchen, luxury beds and hotel quality linens. Every room has cable TV and internet throughout the house.

FamilyLocationKitchen

Top Guest favourite
The charming bungalow features a welcoming front porch with white railings, surrounded by a well-maintained lawn. Mature trees offer shade, and the home's warm exterior blends harmoniously with the lush, green landscape.
Home in Monticello
5 out of 5 average rating, 90 reviews

Dogwood House; Private 2 Bedroom in Monticello, FL

Charming 1950s Florida Bungalow in Historic Monticello Florida Stay at The Dogwood House—a beautifully restored bungalow just steps from downtown shops, dining, and drinks. Pet-friendly for well-behaved pups, this cozy retreat is the perfect mix of comfort and charm. Only 30 minutes to Tallahassee or Thomasville!

LocationFamilyTV

Guest favourite
A welcoming entrance is framed by lush greenery, with a light blue exterior and a pink front door. The porch area is partially covered, featuring a textured stone pathway leading to the door.
Home in Monticello
4.96 out of 5 average rating, 84 reviews

The Pearl Cottage - kid and pet friendly!

Relax with the whole family, well behaved dogs and cats included! The Pearl Cottage is located on a peaceful and charming street in downtown Monticello. A park with a playground is only a couple blocks away. Eat and shop local for the day. Tallahassee is 30 minutes away, Alligator Point is 1hr 20 minutes.

FamilyLocationBackyard

Popular amenities for Monticello holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Monticello

Guest favourite
Home in Monticello
5 out of 5 average rating, 5 reviews

The Hideaway @ Goose Pond Acres

LocationHospitalityView

Guest favourite
A charming brick house is presented, featuring a distinctive blue front door. Lush greenery surrounds the home, with well-maintained shrubs and a spacious front yard of vibrant grass. Large windows with rounded details add character to the structure, complemented by a traditional chimney.
Home in Tallahassee
4.79 out of 5 average rating, 34 reviews

The Farm House at Mahan

LocationFamilyView

Top Guest favourite
A well-appointed kitchen features modern white cabinetry paired with warm wooden elements. Natural light streams through two windows, illuminating the marble countertop and creating a welcoming atmosphere. Open shelving displays decorative items, while a subtle area rug adds texture to the wooden floor.
Home in Thomasville
5 out of 5 average rating, 42 reviews

Charber Farm Cabin

FamilyLocationNearby

Guest favourite
Aerial view of the property reveals a spacious layout with an in-ground pool and surrounding outdoor areas. The well-maintained exterior showcases a large driveway and ample green space, while the interconnected wings of the house provide multiple entries.
Home in Monticello
4.88 out of 5 average rating, 24 reviews

Sunset Blue House - Secluded Pool Home on 4+ acres

FamilyLocationSleep quality

Top Guest favourite
A spacious lakeside home is nestled among lush greenery, with large oak trees providing shade. The exterior features multiple windows and a welcoming deck with railings, surrounded by vibrant foliage. Blue skies and gentle clouds create a serene backdrop.
Home in Tallahassee
4.97 out of 5 average rating, 37 reviews

Lake House with Kayaks & Court 10 mins. to FSU

FamilyLocationQuiet

Guest favourite
A charming cottage is presented, featuring a covered front porch and multiple windows that allow natural light to fill the interior. Lush greenery surrounds the home, enhancing its inviting appearance. Spanish moss drapes from nearby trees, adding to the serene atmosphere of the property.
Cottage in Monticello
4.87 out of 5 average rating, 145 reviews

The Knotted Oak Cottage- Fenced & Dog Friendly

LocationFamilyBiking

Guest favourite
The exterior of a two-story home is showcased, featuring a large front porch with white railings and steps leading to the entrance. A white picket fence surrounds the property, and the design is complemented by lush greenery and trees nearby.
Home in Monticello
4.82 out of 5 average rating, 79 reviews

Charming 2 Bedroom 2 Bath , Private Cabana

ValueFamilyGetting around

Guest favourite
A charming single-story home is set on a lush green lawn, framed by blooming bushes. The grey exterior contrasts with the white shutters, while a welcoming front porch adds to the appeal. Soft clouds hover in the sky, enhancing the tranquil atmosphere.
Home in Monticello
4.94 out of 5 average rating, 17 reviews

Lagniappe, Get a little extra!

LocationValueNearby

When is the best time to visit Monticello?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$213 AUD$218 AUD$215 AUD$214 AUD$222 AUD$210 AUD$203 AUD$208 AUD$210 AUD$222 AUD$218 AUD$205 AUD
Avg. temp11°C13°C16°C20°C24°C27°C28°C28°C26°C21°C16°C13°C

Frequently Asked Questions

  • What are the best places to stay in Monticello?

    Monticello has historic downtown homes, countryside retreats, and cozy cottages, reflecting its small-town character. Choosing a place near the center lets you explore local shops, restaurants, and cultural landmarks with ease.

  • What are the best things to do in Monticello with kids?

    Families can explore local parks for playgrounds and nature trails, visit interactive history museums, or attend community fairs and seasonal events. U-pick farms and farmers’ markets around Monticello give kids a taste of local produce and rural traditions.

  • What are some of the best things to do in Monticello?

    Explore the Monticello Opera House for live performances, stroll through the historic district’s unique architecture, or browse local shops downtown. Nearby parks and small museums add variety to a relaxed itinerary.

  • How is the weather in Monticello?

    Monticello has mild winters, with temperatures around 40–64°F (5–18°C), and warm, humid summers, typically between 71–92°F (22–33°C). Rainfall is higher in the summer, especially from June through August, so lightweight clothes and a rain jacket are often useful.

  • When is the best time to visit Monticello?

    Spring and autumn are often recommended for comfortable weather, with temperatures typically mild and outdoor events taking place across the region. Summer is warmer and more humid, especially from June through August, while winter is generally mild.

  • What are the best places to visit in Monticello?

    Explore the historic district, which has preserved homes and buildings, and visit a community theatre known for local productions. The courthouse square and nearby parks reflect Monticello’s small-town charm and local traditions.

  • What are some hiking trails in Monticello?

    Local parks in Monticello have walking and nature trails suited for observing native plants and birds. Around the area, state parks provide additional options for longer hikes and exploring North Florida’s landscapes.

  • What are some family activities we can do in Monticello?

    Explore local parks with walking paths and picnic spots, or visit a small-town theatre for seasonal performances. Farms and orchards around Monticello often provide hands-on activities, such as fruit picking or learning about local agriculture.

  • What are some of the best day trip ideas from Monticello?

    Many travelers explore nearby state parks for hiking and wildlife watching, or visit locally owned farms and markets around the region. Art galleries and historic towns near Monticello are frequently suggested for learning about North Florida’s cultural and natural heritage.

  • Are there any pet friendly accommodations available in Monticello?

    Many stays in Monticello welcome pets, especially in cottages or countryside rentals. Parks and green spaces around town make it easy to get outdoors with your pet during your visit.

  • What are some local tips for visiting Monticello?

    Many visitors enjoy starting their day at a local café, and chatting with shop owners often leads to insider recommendations. Bring comfortable shoes for walking historic streets, and stop by a Saturday market or seasonal event if your trip aligns.

  • What is Monticello known for?

    Monticello is known for its historic architecture, community festivals, and locally grown produce. The town often draws visitors interested in heritage sites, Southern food traditions, and a relaxed pace of life.

  • What are the best hidden gems to explore in Monticello?

    Many visitors enjoy wandering through historic neighborhoods featuring Victorian-era homes, or discovering local antique shops tucked along side streets. Small art galleries and quiet trails in the countryside provide a peaceful glimpse into Monticello’s creative and natural side.

  • What are the best foods to try in Monticello?

    Southern-inspired dishes like fried green tomatoes, fresh local vegetables, and barbecue are frequently suggested. At local markets and diners, you might find homemade pies or traditional comfort foods reflecting the region’s agricultural roots.

  • What should I bring for a trip to Monticello?

    Pack lightweight clothing, a rain jacket during summer months, and sturdy shoes for exploring parks or historic streets. A hat and sunscreen help with year-round sun, while reusable water bottles are handy for outdoor activities.

  • What is the nightlife in Monticello like?

    Monticello nightlife tends to be laid-back, with local taverns, occasional live music venues, and seasonal community gatherings. Evenings are often spent at local restaurants or attending performances at intimate spaces like the opera house.

  • What are the most popular events or festivals in Monticello?

    Monticello is known for community festivals, such as an annual watermelon festival in summer, holiday parades, and arts and crafts fairs throughout the year. Food vendors, live performances, and local heritage traditions are often highlighted.

  • Are there family friendly vacation rentals in Monticello?

    Monticello has a variety of vacation rentals, including spacious family homes, restored cottages, and properties near parks or open spaces. You can find places well-suited for families, often with yard access or multiple bedrooms.

Destinations to explore