Holiday houses in Greenwood

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Top-rated holiday rentals in Greenwood

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A serene bedroom is showcased featuring a spacious bed with a textured blue coverlet and a decorative striped pillow. A barn door leads to a modern bathroom, while a white brick fireplace adds character. Natural light filters through patterned curtains, enhancing the calming atmosphere.
Home in Marianna
4.85 out of 5 average rating, 104 reviews

Fielder's Choice - 1940s Brick Home Full of Fun

Have fun with the whole family in this stylish place conveniently located near Downtown, Chipola College, and the M.E.R.E (travel ball families-complex 4.5 miles). Fielder’s Choice, a 1940s brick home, is a perfect mix of new and old and packed with fun and games inside and outside! Jackson County’s ecotourism is thriving; 9 bodies of water for fishing, paddling, and tubing; adventure trails-walking and horseback; and Caverns. Explore new flavors in locally curated ice cream & craft beers. Pets!

Top Guest favourite
A welcoming entrance features a screened porch with a decorative door. Surrounding greenery includes trimmed bushes and a tree. The grassy lawn extends beyond, with additional trees in the background, creating a serene atmosphere.
Home in Donalsonville
5 out of 5 average rating, 165 reviews

Peaceful & Beautiful Lake Cabin, Boat House/Dock

Located on beautiful Lake Seminole, a short distance from the hosts main house. Includes use of boat house & dock (you'll need your own boat). 2 boat landings within a mile. Across the lake from Lake Seminole State Park. Within 2 miles of gas station, Dollar General & restaurant. 45min to FL ST Caverns. Free wifi. Full Kitchen is equipped with dishes, pots pans, full size oven/range, refrigerator, microwave, coffee maker. Large flat screen TV, screened in porch and back deck near fire pit

Top Guest favourite
A charming cottage exterior features a welcoming front porch with four white bistro chairs and a small table. Decorative plants frame the entrance, and a teal door is adorned with a wreath. Lush green grass surrounds the structure, complemented by tall pines in the background.
Cottage in Cottonwood
4.98 out of 5 average rating, 128 reviews

Cozy Cottage in the Pines

Enjoy a quiet stay just outside of town on a farm! Listen to the breeze whisper through the pines and relax in this peaceful country setting. The cottage is 2 miles north of Cottonwood and is just under 10 miles to The Ross Clark Circle in Dothan. Dothan has a lot to do…..shopping, dining, and entertainment. Also, the cottage is only a few miles from the Florida line and the Georgia line if you’re going there for something fun! WiFi is fast so working from the cottage is easy as well!

Top Guest favourite
Home in Marianna
4.99 out of 5 average rating, 97 reviews

Millstone on the Millpond-6 miles of Springs

Welcome to Millstone, a luxurious 3BR/3.5BA waterfront retreat designed for relaxation and style. Enjoy mid‑century décor, expansive windows with water views, a gourmet kitchen, and 4 Smart TVs. Steps from the water, enjoy peaceful mornings and elevated comfort. Enjoy unforgettable moments in Millstone. Natural light fills every room. Thoughtfully curated touches enhance both comfort and luxury throughout your stay. Millstone is a space where every moment feels beautifully effortless.

Guest favourite
Home in Sneads
4.91 out of 5 average rating, 32 reviews

The fishing camp

Private dock to fish sunbathe tie boats off to .Boat ramp is across the street,three rivers park is 1000 yards,dirt roads and trails . My place is on Lake Seminole I have a big area for parking trucks with boat trailers and off road vehicles are welcome , animals are welcome . Fenced in side yard , grill , smoker, fish cleaning table , fish fryer, deer hanger for cleaning, outdoor patio area, fire pit, and outside surveillance cameras washer and dryer hot tub

Top Guest favourite
A charming farmhouse exterior is presented, featuring a white facade and a green metal roof. Two rocking chairs are positioned on the porch, complemented by decorative elements. Lush green grass surrounds the home, offering a serene rural view against the backdrop of open fields.
Home in Graceville
4.95 out of 5 average rating, 21 reviews

Windmill Way

A cozy remodeled farmhouse in a quiet rural country setting, but only 2 miles to town. It's surrounded by open fields, barns, cows and windmills. Enjoy the fresh air, nature and the wind blowing through your hair. Windmill Way is inviting with farmhouse decor, soft lighting, comfortable furniture and new appliances to make the space feel like a true home. It's the kind of place where you can just relax, read a book or sit on the porch and enjoy the view.

Top Guest favourite
The historic property, built in 1917, features a two-story façade with spacious porches on both levels. Surrounded by large oak trees, the exterior is complemented by well-maintained landscaping and a flag gently waving, highlighting a serene atmosphere.
Home in Greenwood
5 out of 5 average rating, 20 reviews

The Willis House

Come forget about your worries at this peaceful 6 acre historic property built in 1917. The huge oak trees surround this property making it a built in canopy. This keeps the house cooler in the summer. Sit or walk around the 4500 square feet of porches and catch a breeze or sit and have quite time. The home has been recently remodeled and set to current fire code standards. The house has a lot of room to roam full upstairs and downstairs.

Top Guest favourite
A wooden gazebo is set in a lush green setting, featuring a small table with two chairs. The open structure showcases decorative railing and is surrounded by trees, creating a peaceful outdoor seating area.
Cottage in Marianna
5 out of 5 average rating, 162 reviews

Chipola Woods quiet & cozy near Caverns, Bear Paw

No cleaning fees! Our one & only peaceful, quiet golf cart friendly location conveniently between I-10/US90 yet the Caverns, Bear Paw river float, Merritts Mill Pond, Hinson Nature Preserve, Blue Springs and all shops, cinema, boat launches & restaurants within a 10 min drive. Golfing, beach, & airports within 1 hour. Modern cottage on a private 1/2 acre equipped with large smart TV's in both the living room and bedroom with Prime video.

Top Guest favourite
Home in Marianna
5 out of 5 average rating, 17 reviews

Charming In-Town Bungalow

Unique and stylish home located in a historic Marianna neighborhood. Overflowing with sidewalks, the urban setting is walkable to many city amenities and businesses. Quiet, quaint, and quality! This home is thoughtfully restored to preserve character while adding modern comforts. Spacious and functional! Whether your travel is for business or pleasure, your stay will be cozy and clean.

Top Guest favourite
A comfortable living area showcases a light-colored sofa and an accent chair, arranged around a wooden coffee table. A television is mounted on the wall above a decorative fireplace. In the background, a dining area features a large table surrounded by multiple chairs.
Home in Colquitt
5 out of 5 average rating, 57 reviews

Little City Farmhouse

Keep it simple at this peaceful and centrally-located cottage. Home built in 1910 and recently remodel to create a home the embelishes southern hospitality. Relax on the front porch 3 blocks from the town square and directly across from the new development by the hospital authority. Very quite even during the weekday buzz. Space designed for gatherings and friends.

Top Guest favourite
A wooden sign shaped like a fish indicates 'The Cottage,' positioned on a post. The background features a gravel pathway leading up to the cottage, surrounded by trees and shrubs. Bright sunlight casts a warm glow over the scene.
Cottage in Donalsonville
4.98 out of 5 average rating, 126 reviews

The Cottage! 5 star! Hottub•fishing•dock/lift

Cozy cottage located on Lake Seminole known for it’s Award winning bass fishing! Open floor plan with light and airy colors throughout! Large screen porch overlooking Lake Seminole! Home is less than 50 feet from the shoreline. The lake is visible from almost every room in the home! Come and enjoy the peace and tranquility of Lake Seminole!

Top Guest favourite
A cozy den area features a comfortable brown sofa and armchair, with two lamps providing soft lighting. A flat-screen TV is mounted on a rustic wooden wall adorned with a deer head mount. A plush area rug lies on the floor, adding warmth to the space.
Cabin in Greenwood
4.88 out of 5 average rating, 102 reviews

Country’s best, “Sweet Linda Lodge”

Get away from it all when you stay under the stars in this unique country cabin. Sit on any of 3 porches and enjoy the sunrises and sunsets over the tree lines while listening to the birds serenade . Leave the noisy city life and hectic daily schedules to escape to this cozy cabin in the country.

Popular amenities for Greenwood holiday rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Jackson County
  5. Greenwood