
Holiday rentals in Greenville
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Top-rated holiday rentals in Greenville
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Perfect Cottage on the Lake
Located in Lake Park, GA just south of Valdosta, GA. This cottage is newly renovated inside and out and sits directly on the waters of Lake Long Pond. Enjoy boating, skiing, tubing, canoeing, paddle boarding, fishing and more. Large open floor plan with wall of windows and huge deck overlooking the lake for beautiful sunset views. Long dock with diving board at the end. Private white sandy beach and boat ramp on property. Perfect for gatherings and entertainment. Near Wild Adventures Theme Park.

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.

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].

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.

Twisted Pine Lake Cottage, secluded & near town
Close to everything, a million miles away....... Down the two-track driveway, past the view of the nearest neighbors, our three-bedroom cottage awaits. Rest easy on the patio, 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.

Amazing Private Cabin w Pool & Fishing Pond
A serene stay awaits you as the beauty of nature overwhelms and true privacy surrounds on acres of land. Stay in this secluded log cabin, which includes a stocked pond & sparking pool. Just a short drive to I-75 or to town. Gated entrance that leads you down a paved road that opens up to a large, well-maintained lawn & pond with the cabin in the background. The cabin itself has exposed beams & rustic beauty. The wrap-around porch has a lovely view of the pond & pool. Memories Await;)

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.

Best memories are made on the Suwannee River
*** Inquire about Winter rates for Jan 2027 through March 2027*** Located on the banks of the historic Suwannee River! Enjoy making memories and explore Florida's nature at its best! Visit nearby Lafayette State Blue Springs Park where you can take a dip in a refreshing spring or Wes Skiles Peacock Springs State Park located in Luraville for some cave exploration or just relax and take in natures beauty while sitting on the dock.

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.

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.

Gulf Front Sunset Right on the Gulf
Our 2 bedroom 1 bath house sits on high stilts directly overlooking the Gulf of Mexico. Located in undiscovered Dekle Beach, Florida. It is a retreat from everything. We are about three miles up the coast from Keaton Beach. Known for scalloping! Three open bays for your vehicles. Boat launch one block away. Beautiful sunsets, stargazing, birding, reading, fishing and scalloping during the season.

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.
Popular amenities for Greenville holiday rentals
Other great holiday rentals in Greenville

Welcome to The Schoolhouse

All Decked Out

Home in Monticello near downtown w/ modern vibes

Family Fun at the Lake

Papa’s House: Country Getaway with Pond View

Walk to historic Monticello from this newer home

Dogwood House; Private 2 Bedroom in Monticello, FL

Camellia Cottage (Wheelchair friendly)
Destinations to explore
- Four Corners Holiday rentals
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- Florida State University
- Shell Point Beach
- Madison Blue Spring State Park
- Alfred B. Maclay Gardens State Park
- Wild Adventures
- Doak Campbell Stadium
- Fred O. Drake Park at Lake Ella
- Cascades Park
- St. Marks Lighthouse
- Tom Brown Park
- Edward Ball Wakulla Springs State Park
- Tallahassee Automobile Museum
- Suwannee River State Park
- Backwoods Crossing
- Story Lake





