Holiday houses in Greenville

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Top-rated holiday rentals in Greenville

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Guest favourite
A wooden dining table is surrounded by six rustic chairs, positioned in a warmly lit space. Natural light filters through the blinds of a large window, illuminating the wooden walls. A wooden cabinet is present in the corner, enhancing the cabin feel.
Cabin in Live Oak
4.92 out of 5 average rating, 233 reviews

Florida Country Cabin Getaway

Nestled in the heart of rural North Florida, this picturesque log cabin on 3 acres offers a tranquil retreat enveloped by majestic oaks and towering pines. Stepping inside, they find themselves embraced by the warmth of a cozy interior, where comfortable furnishings invite relaxation. However, the true allure lies where a sprawling outdoor deck beckons guests to unwind amidst the serenity of nature while enjoying their morning deink from the extensive selection of coffee, tea and hot chocolate.

Guest favourite
A spacious living area features a large brown leather sectional sofa complemented by a light-colored area rug. Natural light streams through the two large windows, highlighting the wooden beams on the ceiling, and a flat-screen TV is mounted on the wall above a stylish entertainment unit.
Home in Madison County
4.96 out of 5 average rating, 23 reviews

Val's Country Place

3rd-4th guests only $95/person/night Take a break and unwind at your peaceful country oasis. Nestled among farms and quiet dirt roads, a great experience awaits you. Enjoy the yard’s pecan trees and close-by Madison Blue Spring State Park. Madison is home to many antique shops and unique stores. Find historical mansions and tours in this quaint town. Bring your camera; enjoy the melodious birds by day, neat pine-lined sunsets at dusk, and truly spectacular star filled sky by night. Enjoy!

Top Guest favourite
A cozy A-frame Hobbit House is set amidst natural surroundings. A fire pit, surrounded by a circular stone base, holds logs ready for a fire. Nearby, a picnic table and wooden chairs provide seating under the shade of large oak trees.
Campsite in Lee
4.96 out of 5 average rating, 194 reviews

A-frame near Madison Blue Springs

Get away from it all when you stay under the stars. Our A-frame Hobbit House is cozy and dry and sleeps 2 . The Aframe has electricity and AC in the summer months and heater for the cooler months. There is an outdoor bathhouse that is shared with the other people on the property. Outside, there is a picnic table, chairs, gas grill with burner, and firepit. You are welcome to use the firewood found on our property. Please note we have two very friendly golden retrievers and chickens on property.

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.

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, 109 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].

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, 170 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.

Guest favourite
A log cabin with a striking red metal roof is surrounded by lush greenery and mature trees. The porch extends along the front, providing a welcoming entry. A spacious yard features a natural landscape, creating a serene environment for relaxation.
Cabin in Mayo
4.96 out of 5 average rating, 114 reviews

Red Bird Cabin-Peace & Quiet Near the River

Log Cabin, 3 Bedrooms, 2 Baths, (Sleeps 6) -450 yards to the Suawnnee River. Come enjoy the peace and quiet at Red Bird Cabin with 16 private acres on the historic Suwannee River. Surrounded by giant, sleepy live oaks, lemon, and orange trees, you will thoroughly enjoy getting away from it all! The property is a wonderful retreat with a large, open yard and gorgeous views. Bring your fishing poles. Bring your boat! There is a private boat landing on the property 450 yards from the cabin.

Top Guest favourite
A serene lakeside view is framed by tall cypress trees covered in Spanish moss. The tranquil water reflects soft pink and orange hues of the sunset, while a grassy area leads toward the lake, enhancing the peaceful atmosphere.
Place to stay in Pinetta
4.95 out of 5 average rating, 128 reviews

A piece of heaven on Cherry Lake

A piece of heaven at Cherry Lake will have you feeling heavenly during your stay! On the waterfront property sit a two bedroom, one and a half bath trailer that has the feel of a cozy home. Dogs welcome with a one time pet fee. Cherry Lake is located in Madison County, south of Valdosta GA. The city of Madison has a historic district and one of the cutest downtowns in Florida lined with antique shops and locally owned eateries.

Top Guest favourite
The charming exterior of a blue house is displayed, featuring a gabled roof and an inviting orange door. A landscaped walkway with newly planted greenery leads up to the covered porch, which includes a small seating area. Sunlight brightens the scene.
Home in Quitman
4.96 out of 5 average rating, 372 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 with a pet fee and rules.

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, 167 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.

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, 87 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!

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, 82 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.

Popular amenities for Greenville holiday rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Madison County
  5. Greenville