Holiday rentals in Greenwood

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Top-rated holiday rentals in Greenwood

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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, 139 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 1/2 acre equipped with large smart TV's in both the living room and bedroom with Prime video. Queen pullout sofa w/mattress topper for extra comfort *on request

Superhost
A comfortable living area features a plush green sofa facing a wooden entertainment unit with a large TV. A round coffee table sits on a woven rug, and natural light enters through a nearby window, illuminating the space's neutral tones.
Apartment in Dothan
4.93 out of 5 average rating, 134 reviews

Lux Living near Downtown Dothan & Hospitals

Welcome to this thoughtfully designed space that just finished construction! Remote work here is a breeze, with WiFi speeds of 550mbps. Extended stays welcome! While there's all the privacy you'll need, this location makes it easy for you to get around You are only: 6 mins to South East Medical Center 7 mins to the heart of Downtown Dothan 8 mins to the Alabama College of Osteopathic Medicine 13 mins to Westgate Park & Flowers Hospital 1.5 hrs to PCB & surrounded by endless local restaurants!

Guest favourite
An outdoor pool area is enclosed by a white fence, featuring a large blue swimming pool complemented by a spa. Comfortable lounge chairs are arranged around the deck, and a gazebo provides shaded seating. Tall trees and clear blue skies create a serene backdrop.
Guest house in Chipley
4.95 out of 5 average rating, 374 reviews

Guesthouse & Pool

This family friendly home is less than 2 miles from Walmart and restaurants. Wifi, Netflix, and Prime video are included with your stay. There is one queen bed, one full bed, a queen size sleeper sofa, and a twin. All of which can accommodate a total of 7 guests. Chipley is located off I-10. It is a 55-minute drive to the beach and a 45-minute drive to Dothan, AL. Falling Waters State Park is 3 miles away. Caverns park 15 miles. No pets and no smoking allowed. Home is sanitized between guest.

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, 153 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

Guest favourite
A relaxing outdoor space features four blue chairs arranged around a fire pit, set against a scenic lakeside view. The backdrop showcases a tranquil lake at sunset, with reflections of vibrant orange and purple hues in the water. Tall trees frame the area, enhancing the peaceful atmosphere.
Home in Donalsonville
4.88 out of 5 average rating, 214 reviews

“The Q'whack Shack" on Lake Seminole with Dock

Aptly named, “The Q'Whack Shack,” our quaint lakefront home is the perfect host accommodation for a charming weekend or weeklong reprieve. Ideally situated on the heart of Lake Seminole, The Q’Whack Shack is a water enthusiasts dream hideaway. Enjoy boating, angling, an array of watersports (skiing, tubing, etc.), grade-A bass fishing and duck hunting with convenient private dock access just steps from the back door. Waterfront restaurants and other provisions just a quick boat/car ride away.

Superhost
The sleeping area features two beds, one spacious and one twin size, neatly made with grey bedding. A dark dresser with decorative hardware stands beside the larger bed. A colorful horse-themed artwork adorns the wall, and a lamp provides soft light, enhancing the cozy ambiance.
Guest suite in Greenwood
4.76 out of 5 average rating, 86 reviews

The Studio

The Studio is an apartment set up with an Ikea couch easily converted to a queen size bed & a twin size bed. It has a private entrance &yard. My place is close to Florida Caverns State Park, Bellamy Bridge, Blue Springs Recreational Area. You’ll love my place because of the quiet area and coziness. It's good for couples, solo adventurers, business travelers, families, and furry friends (pets). See our other listings, Florida Caverns Cottage Single Room & Bunk Rooms if you have a large group.

Top guest favourite
A wooden swing is suspended from a sturdy tree branch, overlooking a peaceful pond surrounded by lush greenery. The water reflects the clear blue sky, and the distant tree line creates a serene backdrop, inviting relaxation and contemplation.
Cottage in Dothan
4.99 out of 5 average rating, 210 reviews

Juju’s Pond House on Smith Pond

Take it easy at this unique and tranquil getaway located on 100 acres and nestled quietly on a private pond. The house was originally built in 1921 and in 2018 we had the house moved down to the pond and did a full renovation while preserving as much original character as we could. Enjoy your morning coffee and watch the sunrise from the screen porch swing or one of the docks at the pond. The property has nature trails to explore, fishing, and plenty of wildlife.

Top guest favourite
A wooden porch swing is suspended from a support beam, positioned to overlook an open field. A vibrant sunset fills the horizon, blending soft hues of pink and orange against a backdrop of trees. The tranquil landscape invites moments of relaxation.
Tiny home in Ashford
4.95 out of 5 average rating, 106 reviews

Barndo“mini”um

Peaceful, private country retreat with beautiful views and friendly cows in the backyard. Enjoy your morning coffee on the porch swing and relax in the ultra-comfy bed after a quiet, restful night. Includes full-sized fridge, microwave, toaster oven, TV, Wi-Fi, and full bathroom. Just 10 minutes from Farley Nuclear Plant and 13 minutes from Southeast Health. Perfect for relaxing stays or quiet work trips. Come enjoy our little slice of paradise!

Guest favourite
A softly colored bedroom features a spacious bed with a decorative quilt and a wooden headboard. Natural light streams in from large windows, illuminating the room. A sliding glass door leads to a private deck, adding to the bright and open feel of the space.
Flat in Dothan
4.91 out of 5 average rating, 476 reviews

Claire’s Cottage with privacy gate

Everything you need in a quaint, modern space located on 7 secluded acres with a privacy gate only minutes from the Ross Clark Circle and downtown, Wi-Fi, Smart TV with YouTube TV subscription included (over 70 channels), brand new fridge, spacious rooms. Washer and dryer available. We allow pets on a case by case basis and charge a one time $10 fee per pet upon guests arrival. We also offer EV level 2 charging (40 amp) for a flat $10 fee.

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, 114 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!

Guest favourite
A single-story home is set against a backdrop of lush greenery. A green canoe rests on the grass in the foreground, while the house features a simple exterior with a covered porch. Windows allow for natural light, inviting the outdoors inside.
Cabin in Marianna
4.92 out of 5 average rating, 201 reviews

A beautiful place

Located on the Chipola River in historic Marianna, Fl. 2 canoes available for your use. Large deck you can fish from. Dock on the river for swimming or launching canoes. Home of the World famous Florida Caverns State Park. Also one of Florida's biggest blue holes "Blue Springs". Only 1 hour from Panama City Beach.

Guest favourite
A charming art studio is set among lush greenery, featuring a gabled roof and large windows that allow natural light to fill the interior. A stone pathway leads to a wooden bench positioned on a manicured lawn, surrounded by diverse foliage.
Farm stay in Hartford
4.89 out of 5 average rating, 335 reviews

Hartford Art Studio and Loft

This treasure is a stand alone art studio with a loft surrounded by beautiful lawn and gardens. The Studio is 45 feet (read close) to the house. There are agricultural fields on three sides. The artist, Beverly Mayfield, is now deceased, but has filled the studio with masterful paintings.

Popular amenities for Greenwood holiday rentals

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