
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.

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

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. - Smoking: Outside! [Medical also outside]. Nic Vape OK in.

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.

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.

Fisherman’s Oceanfront Dream Home w/Dock & Kayaks
35% discount for monthly stays, 15% for weekly. Million$$ views of Oyster Bay & Gulf from every room. Only 40 minutes to the Florida Capital, FSU, & the Tallahassee International Airport. Private floating dock & trailer parking. Screened porch & 2 walkout decks. Views from any room are breathtaking! Enjoy the hammock under the house. Kayaks, fish cleaning station With the well appointed kitchen, gas grill & laundry you will have everything you need. (boat lift not available)

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.

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.

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.

All Decked Out
Escape to a fully furnished lakefront retreat on Cherry Lake, just outside Madison, Florida, where relaxation and adventure meet. This spacious home comfortably sleeps up to 10 guests with three bedrooms, two bathrooms, and a cozy loft with an additional bed. Nestled beneath grand North Florida live oaks, the property exudes Southern charm and offers stunning lake views from nearly every room.

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

Dogwood House; Private 2 Bedroom in Monticello, FL

Home in Monticello near downtown w/ modern vibes

Family Fun at the Lake

Papa’s House: Country Getaway with Pond View

Camellia Cottage (Wheelchair friendly)

Walk to historic Monticello from this newer home

Peaceful cabin on the Cochee River w/ 4 acres land

Bogetti Family Farm
Destinations to explore
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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
- Story Lake
- Cascades Park
- St. Marks Lighthouse
- Tom Brown Park
- Edward Ball Wakulla Springs State Park
- Tallahassee Automobile Museum
- Suwannee River State Park
- Backwoods Crossing





