Vacation rentals in Greenwood

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Top-rated vacation rentals in Greenwood

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Guest favorite
A wooden deck is surrounded by tall trees, providing a natural backdrop. A small round table is set with a few plant pots and decorative items. Metal chairs are positioned around the table, inviting moments of relaxation in a serene outdoor setting.
Home in Graceville
4.92 out of 5 average rating, 99 reviews

Cozy & quiet House in the country

Relax with the whole family at this peaceful place. Please note there is NO WI-FI at this location. Feel free to Bring your dog and enjoy a fenced in back yard. We are happy to assist with directions and recommendations! •2 miles from the silos wedding venue . • 14 miles from Falling waters state park ( biggest waterfall in FL) • 29 miles from Florida caverns state park • 33 miles from Ponce de Leon State park • 38 miles from Econfina Creek ( Natural Springs ) • 27miles from Cypress Springs

Top guest favorite
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.
Guesthouse in Chipley
4.96 out of 5 average rating, 411 reviews

Guesthouse & Pool

This family friendly home is less than 2 miles from Walmart and restaurants. Wifi, Netflix, Starz, Prime video are included with your stay. There is one queen bed, one full bed, a queen size sleeper sofa, & 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 & no smoking allowed. Home is sanitized between guests.

Top guest favorite
A poolside patio is shown, featuring two blue chairs with colorful cushions. In the background, a private entrance leads into a spacious area with a table set for dining. Lush greenery and a pool are visible, creating a tranquil outdoor setting.
Guesthouse in Colquitt
4.93 out of 5 average rating, 128 reviews

Country Casita

Nestled in the peaceful countryside of Miller County, GA, this cozy cottage offers the perfect mix of relaxation and small-town charm. Just 1.5 miles from the Colquitt town square, you’ll be close to local shops & family-owned eateries. Unwind on the poolside patio, enjoying views of open pastures and pine branches overhead. It’s the ideal setting for a quiet country stay. Amenities: microwave, Keurig, toaster oven, mini fridge/freezer, grill, bathroom, shower, A/C, outdoor patio/dining area.

Guest favorite
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, 223 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.

Guest favorite
A gaming area is highlighted by a large ping pong table centrally positioned, with a ceiling fan above providing comfort. A dartboard is mounted on the wall, and a television is visible nearby, streaming entertainment. The space is finished with neutral walls and wooden accents.
Home in Dothan
4.93 out of 5 average rating, 199 reviews

Comfy 3 bedroom house with hot tub and game room.

Relax and unwind in this space, or even come to work or play. You will have the entire 3 bedroom, 2 full bath house to yourselves. Equipped with washer/dryer, kitchen, hot tub, work space, Wi-Fi, and even a little bar with ping pong table & dartboard. This is our house we have been remodeling and use as our own little getaway on date night, it’s far from upscale fancy, but it is cozy and with a soak in the hot tub can even be romantic. Welcome gift provided, message with any special requests.

Top guest favorite
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
4.97 out of 5 average rating, 111 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!

Superhost
A spacious single-story home showcases a modern design, featuring a light-colored brick exterior and dark brown garage doors. The front yard is adorned with manicured grass, while large windows allow natural light to enter. Tall trees frame the property, enhancing its serene setting.
Home in Dothan
4.87 out of 5 average rating, 166 reviews

Twin Pines | Luxury Getaway

Welcome to Dothan's Gem! A beautifully designed dream home! Bringing the whole family? Working remotely? Rest assured, you'll have high speed internet no matter what, with speeds up to 500mbps! While there's plenty of privacy, this location makes it easy for you to get around You are only: 4 mins to Flower's Hospital 5 mins to Westgate Recreation Park 5 mins to Forever Wild Trails 10 mins to the heart of Downtown Dothan 1.5 hrs to PCB & surrounded by Dothan's best restaurants!

Top guest favorite
Townhouse in Dothan
5 out of 5 average rating, 148 reviews

2 BR 2.5 BTH, 3 Beds,Dog Friendly, Stocked Kitchen

Experience the best of Dothan in this stylishly renovated townhome. Perfectly situated for adventure, just moments from championship golf at RJT and DCC, thrilling water fun at Water World, exciting games at the Westgate Baseball and Tennis Complex, the serene beauty of Forever Wild trails, and conveniently close to both area hospitals. Unwind in comfort with a fully equipped kitchen, perfect for whipping up delicious meals and stay connected with the blazing-fast Wi-Fi.

Top guest favorite
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, 223 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.

Guest favorite
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, 16 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 favorite
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, 146 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.

Superhost
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
4.9 out of 5 average rating, 207 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.

Popular amenities for Greenwood vacation rentals

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