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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 $68 NZD 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
Cottage in Thomasville
4.96 out of 5 average rating, 490 reviews

Cottage 308-Walk to Downtown-Historical-King Bed

Welcome to Cottage 308! This adorable 1863 historical home is loaded with charm! Come enjoy its' towering tall ceilings, arched doorways, and quaint spaces for your perfect get away! Located in peaceful, Victoria Place and within walking distance of the brick streets of downtown Thomasville. This one bedroom, one bath home hosts a king bed, lovely walk in shower, fully furnished kitchen, laundry room and coffee bar! All the charm of this home awaits you to make your stay one of a kind! Welcome!

FamilyLocationParking

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.

FamilyLocationAccuracy

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.

FamilyLocationIndoor spaces

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, 201 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.

FamilyLocationQuiet

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].

LocationValueCondition

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.

LocationFamilyBarbecue

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.

ValueFamilyQuiet

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, 188 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

ValueLocationAmenities

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, 255 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

FamilyValueWalkability

Top Guest favourite
A comfortable living area features a light-colored sofa centered on a wood floor. Two lamps with dark bases and soft shades are positioned on either side on small tables. Soft light illuminates the space, enhancing the layout's inviting feel.
Home in Monticello
4.96 out of 5 average rating, 83 reviews

Charming cottage located on a historic street.

The Camelia Cottage is located on charming Pearl Street, surrounded by historic antebellum homes. Enjoy quiet evenings in this unique neighborhood. Camelia Cottage is within 30 minutes of Tallahassee and within walking distance of quaint shops and restaurants. You will certainly enjoy the small town atmosphere. Camelia Cottage has recently been updated, there are two beds one king and one full bed.

ValueFamilyWi-Fi

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, 171 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.

FamilyLocationBackyard

Top Guest favourite
A charming single-story home is surrounded by trees, featuring a spacious deck with seating areas. Two chairs are positioned on one side, while a dining table and chairs are located nearby. A gentle slope of grass leads to the deck, enhancing the serene outdoor setting.
Home in Thomasville
4.96 out of 5 average rating, 113 reviews

Spacious home - all bedrooms have a private bath

Spacious home with room for the whole family! Peace and serenity await in this tranquil property that sits on over 1 acre in the charming town of Thomasville. Each of the three bedrooms has its own private bath. This fully equipped and professionally decorated home is ready for a relaxing and comfortable getaway.

LocationValueOutdoor spaces

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

LocationCheck-inHospitality

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

FamilyLocationCleanliness

Top Guest favourite
Campervan/RV in Monticello
5 out of 5 average rating, 46 reviews

Donavon's Rentals

ValueLocationBreakfast

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

FamilyLocationWi-Fi

Guest favourite
A wooden cottage is surrounded by lush greenery, featuring a welcoming front porch and a wooden walkway. The structure showcases green shutters and a gently sloping roof, integrating harmoniously with the natural landscape. Path lighting adds a soft touch to the inviting approach.
Guesthouse in Monticello
4.96 out of 5 average rating, 51 reviews

Cozy Country Cottage near Tallahassee

FamilyValueCondition

Top Guest favourite
The exterior of the Little Green Guest House showcases a charming green facade and classic architectural features. A covered carport is present on one side, surrounded by well-maintained landscaping and mature trees, contributing to a serene residential setting.
Guesthouse in Tallahassee
5 out of 5 average rating, 83 reviews

Lovely guesthouse with outdoor space/near I10

FamilyLocationOutdoor spaces

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

LocationFamilyParks

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

LocationFamilySolo travel

When is the best time to visit Monticello?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$255 NZD$262 NZD$258 NZD$257 NZD$267 NZD$251 NZD$243 NZD$250 NZD$251 NZD$267 NZD$262 NZD$246 NZD
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