House vacation rentals in Headland

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Top-rated house rentals in Headland

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

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Top guest favorite
The open-concept living area features a light-filled space with ample seating, including a gray sofa and a plush armchair. A large flat-screen TV is mounted on a wooden media console against a white wall. Bright natural light filters through the nearby window dressed in sheer curtains.
Home in Headland
5 out of 5 average rating, 68 reviews

"Dixieland Delight". Entire Home- Newly Built!

Newly built 2bed/2bath peaceful getaway in the heart of historic and charming Headland, AL! Open-concept living area. Ample seating and a large flat-screen TV! 2 bedrooms and 2 full baths. The master bedroom offers a king-sized bed and an en-suite bathroom. The 2nd bedroom has a full-sized bed and an additional bathroom is conveniently located in the hallway. Explore charming downtown Headland, visit the nearby Headland Square, or head into Dothan for shopping, restaurants, and entertainment.

Guest favorite
The spacious living room features two comfortable green sofas arranged around a central coffee table. A large flat-screen TV is positioned against a white brick fireplace, complemented by large windows with floral curtains. Warm lighting is provided by two lamps on either side.
Home in Dothan
4.86 out of 5 average rating, 49 reviews

Retro Ranch - 3/2 - Cool & Convenient

You’ll love this comfy, relaxing, unique, conveniently located home! Highly rated! Enjoy the two newly remodeled bathrooms, spacious den with 65” Roku TV, comfy beds, dedicated workspace, stocked kitchen, free Wi-fi, large fenced backyard, gas fireplace, parking for 4 vehicles, covered outdoor porch, and large gas grill. Great for traveling workers! 2 bedrooms with queen beds & 1 with 2 twin beds. Roku tv’s in 2 bedrooms. Home is pet friendly! Weekly and monthly discounts! Book your stay today!

Top guest favorite
A single-story house features a covered front porch with two chairs positioned on either side of the entrance. Lush green grass surrounds the home, and flower beds with small plants are visible near the foundation. A large tree is seen in the background, adding to the outdoor space.
Home in Dothan
5 out of 5 average rating, 21 reviews

Home in Dothan Quiet area outside the circle

Great location- Easy access to Ross Clark Circle. Circular driveway to hold work trucks or a boat. Quiet road. Home sits on 1 acre of land. Fenced in back yard. 3 Bedrooms. 1 Bath. 2-Carports. Located 2 miles to Ross Clark Circle & 4 miles to Southeast Medical. Soccer Fields, bike/walk trails, water parks, dining & shopping all just a short drive. The Chattahoochee River, Farley Nuclear Plant & GP are w/in 10 miles. Panama City Beach is only 90 miles away. Dothan Airport is 15 Miles.

Top 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
4.96 out of 5 average rating, 184 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.

Guest favorite
The exterior of the home features a welcoming front porch with rocking chairs, framed by well-maintained landscaping. The house is a single-story structure with white siding, blue shutters, and an oval front door. Steps lead up to the porch from the yard.
Home in Midland City
4.79 out of 5 average rating, 34 reviews

High Cotton Cottage

Relax with the whole family. Newly remodeled with everything you need. High Cotton is 3 BR 1 Bath is a quiet, safe home. Sit in rocking chairs on the front porch and look out over the cotton field. Well stocked kitchen, washer and dryer, WiFi, Smart Tv's, Coffee and more. 2 queen beds and a single. This place has all the amenities you and your family need for the perfect getaway. 5 miles to Dothan shopping Walmart, Target, cinemas and much more. 3 miles to Dothan Airport. 12 miles to Ozark.

Top guest favorite
A welcoming brick cottage is set on a quiet cul-de-sac, featuring a covered porch with seating. The well-maintained garden surrounds the entryway, and a driveway leads to the home, framed by mature trees and lush greenery.
Home in Dothan
4.97 out of 5 average rating, 30 reviews

Your Home Away from Home

Quaint and cozy cottage nestled on a quiet cul-de-sac in Dothan's Garden District blocks from trendy downtown, Dothan Country Club, Future Masters, The Grand, The Plant, Dothan Opera House & Civic center, Westgate Park/Sports Complex, 4 miles to Southeast Alabama Medical Center, Flowers Hospital, ACOM Alabama College of Osteopathic Medicine, 5 miles from Troy University Dothan & airport. It is a beautiful area to walk or drive around, especially when the Azaleas are in full bloom!

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
4.92 out of 5 average rating, 154 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
A welcoming porch area features a white wicker rocking chair beside a small wicker table. A potted plant is positioned next to the chair, enhancing the tranquil outdoor setting. A striped area rug adds a touch of color to the space, with greenery visible in the background.
Home in Dothan
4.97 out of 5 average rating, 101 reviews

Miss Pearl's House: Charming and Unique 3 bedroom

The whole group will be comfortable in this spacious and unique space. Miss Pearl's House is a 3 bedroom 2 bath home in The Garden District. Centrally located, it is near the best of everything Dothan has to offer. Great detail was given to making the beds deliciously comfy including duvet covers and 12 inch memory foam mattresses, all brand new! If you like your TV large, there is an 82" Samsung with all of the apps. The Wifi is FAST and FREE and the coffee is yummy.

Guest favorite
Home in Dothan
5 out of 5 average rating, 14 reviews

Fall Rate Special! Brad's Baywood Ranch

This beautifully renovated ranch is your perfect launchpad for exploring Dothan! Tee off at championship golf, make a splash at Water World, hike the Forever Wild trails – all within easy reach. Evenings are made for fun in the dedicated game room, complete with classic arcade games, ping pong, and a 65" TV for movie nights or gaming marathons. This pet-friendly haven also features a fully equipped kitchen, large fenced yard, and blazing-fast Wi-Fi!

Top guest favorite
A light-filled living area showcases two comfortable sofas adorned with decorative pillows. A wooden coffee table with intricate detailing sits at the center, surrounded by a soft area rug. Tall windows are dressed with elegant drapes, enhancing the inviting ambiance.
Home in Dothan
5 out of 5 average rating, 136 reviews

Elegant house in the Heart of Dothan

Whether you are in Dothan for work or visiting, we hope you will enjoy your accommodation in our comfortable spacious house! You will find an open living area, well equipped kitchen, three bathrooms, and three bedrooms with comfortable king and queen size beds. The house also has high speed internet and two Smart Roku TVs for your work or entertainment. Please, remember, we can host max 6 guests. No visitors allowed. No family meetings or gatherings.

Guest favorite
A century-old house is depicted, set on expansive grassland and partially shaded by surrounding trees. The structure features a welcoming front porch with steps leading up to a red door. Clear blue skies and scattered clouds provide a serene backdrop.
Home in Columbia
4.93 out of 5 average rating, 123 reviews

The Blackshear Place

A 100 year old house on land that was homesteaded in the 1800’s. Plenty of character, peaceful, private and quiet. 18 minutes from Ross Clark Circle, Dothan Al., 15 minutes from Headland Al. 19 minutes from Blakely Ga. 15 minutes to Log Cabin Restaurant in Georgia and Huggin Molly’s in Abbeville Al. Nearest grocery and gas is 10 minutes in Columbia Al. No WIFI hot spots work well Verizon tower 2 miles away

Top guest favorite
A cozy entryway features a welcoming sign mounted above a decorative wreath on white shiplap. Two hooks are positioned above a built-in bench, which is adorned with two soft decorative pillows in neutral tones.
Home in Dothan
4.95 out of 5 average rating, 161 reviews

Cozy Cottage

Kick back and relax in this calm, stylish space. This cozy cottage sits on 40 acres and over looks the water where you can sit on the dock to fish or relax. The cottage is just newly built and has a front porch where you can enjoy nature.

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