Vacation rentals in Greenville

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Top-rated vacation rentals in Greenville

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Top guest favorite
An aerial view showcases a rustic cabin situated by a serene private lake. The reflection of the surrounding trees is visible on the water's surface. A spacious porch with a roof extends towards the lake, offering a peaceful spot for relaxation.
Cabin in Pavo
4.97 out of 5 average rating, 337 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

Top guest favorite
Apartment in Tallahassee
4.98 out of 5 average rating, 196 reviews

Live Oak Cottages II InTown-Nature 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

Top guest favorite
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.

Top guest favorite
A spacious kitchen showcases modern white cabinetry and a large island with seating for four. Stylish pendant lights hang above the island, and stainless steel appliances are integrated into the design. A cozy living area is visible in the background, providing a seamless flow to the space.
Home in Jennings
4.96 out of 5 average rating, 212 reviews

Gated 5 acres with fitness, 5 tvs, king bed

There's plenty of boat and trailer parking on gated property. 3 types of coffee makers. Keurig ( with pods), French press, Drip. Quiet, secluded, New custom home on 5+ acres. 6-7 min off I75 Kick back and relax in this calm, stylish space. Peaceful Country Living meets Luxury and Style. Nearby Fun: 1. Jennings GP- Motor Track 2. Spirit of the Suwanee 3. Madison State Blue Park -Madison River 4 Wild Adventures - 30 Min 6. Cross Roads Metroplex 7. The Florida HikingTrail and much more...

Guest favorite
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, 110 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 favorite
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, 173 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.

Top guest favorite
A wooden deck features a glass table surrounded by teal chairs, offering a view of the lake. Stone pavers lead through lush green plants and palm trees, enhancing the outdoor space. A large red umbrella provides shade, complementing the tranquil lakeside setting.
Apartment in Lake Park
4.95 out of 5 average rating, 165 reviews

Lake Front Apartment ~Creek side~

Come relax at the lake. This newly renovated efficiency apartment is nestled away on tranquil Dykes Pond. With water on two sides, a babbling brook and full lake access it’s perfect for watching fish and other wildlife, swimming or kayaking. There’s a dock for fishing or for just enjoying the lake view. The apartment, in a multi unit house, is just for you. Kayaks are available for your use. Only 8 min to I-75, 19 min to Wild Adventures, VSU, & SGMC Please note that there ISN’T A KITCHEN!

Top guest favorite
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, 29 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.

Top guest favorite
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 favorite
The treehouse is elevated on stilts, surrounded by lush greenery and ancient oaks. A spacious deck with wooden railings features steps leading to the ground, while decorative plants enhance the outdoor space. The structure showcases large windows, allowing natural light to fill the interior.
Treehouse in Tallahassee
4.99 out of 5 average rating, 124 reviews

Shangri-La Treehouse

Shangri-La Treehouse is the 1st and only luxury treehouse in Tallahassee, Florida's Capital City. Nestled between ancient oaks, Shangri-La Treehouse is luxury in the wild where serenity is found. You are invited to enjoy 9.5 acres of verdant land amidst ducks, deer, owls, and other assorted wildlife that call Shangri-La home. A thoughtful, adults only (21+) romantic getaway for 2 that can accommodate up to 4 guests comfortably.

Guest favorite
The single-story home features a front porch, framed by shrubs and trees. A well-kept lawn surrounds the house, with pathways leading to the entrance. Flower beds add a touch of greenery, complementing the neutral exterior of the property.
Home in Monticello
4.95 out of 5 average rating, 62 reviews

Home in Monticello near downtown w/ modern vibes

This entire home has plenty amenities. The 1562 sq ft. corner is home near downtown. The home is cozy, comfortable and functional for humans only. I hope your stay allows you to enjoy your spouse, family, friends or co-workers. Make sure you create lasting memories as you relax, attend college games, graduations, work or just need a nice place to stay. Tallahassee or Thomasville are only a 30-35 minute drive away.

Top guest favorite
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, 373 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.

Popular amenities for Greenville vacation rentals

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