Vacation rentals in Headland

4.99 out of 5 average rating, 97 reviews

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

"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.

Superhost

Apartment in Headland

Downtown Main St. Gem - Loft 5

We created Loft 5 as a quiet retreat above Headland's storybook town square - a place where you can slow down, reconnect, and feel wrapped in history and charm. From the moment you step outside, you're beneath sweeping oak trees, steps from colorful murals, live music, and candlelit dinners just down the sidewalk. It's the kind of place made for lingering walks and unhurried moments together. Close to Farley Nuclear, Southeast Health, Flowers Hospital and wedding venues. Come and stay a while!

4.83 out of 5 average rating, 6 reviews

A light-filled living area showcases a soft-colored sofa and a patterned armchair. A round dining table with four chairs is located in the background, while the open kitchen features white cabinetry and modern appliances, enhancing the space's inviting layout.

4.87 out of 5 average rating, 79 reviews

Comfortable and Stylish | Live Like a Dothan Local

Kick back and relax in this calm, stylish space. - Located 3 blocks from US 231 North, a few blocks away from Westgate Park, and less than a mile from Flowers Hospital - Fully equipped kitchen; bathrooms with all the essentials - Fast Wifi - Smart TV with Disney+, YoutubeTV, Netflix - 4 miles to downtown Dothan, 1 mile to Flowers Hospital, 7 miles to Southeast Health, 9 miles to the Alabama College of Osteopathic Medicine, 5 miles to Robert Trent Jones Highland Oaks, 5 miles to Dothan Airport

The open living room showcases vaulted ceilings and a central fireplace, complemented by a large wall-mounted TV. Comfortable seating is arranged around a coffee table, while a cozy armchair is positioned nearby, inviting relaxation. Natural light fills the space through the nearby windows.

4.95 out of 5 average rating, 73 reviews

Azalea Place - Comfy 3/2 On Quiet Culdesac

Spacious king suite with soaking tub, walk-in closet, workspace, ceiling fan, & 55” Roku TV. Open living area with vaulted ceilings, fireplace, 65” TV, ceiling fan, & cozy seating for movie nights. Fully stocked kitchen with coffee bar. Guest rooms have queen beds, Roku TVs, ceiling fans, & large closets. Two full baths, both with tub & shower. Peaceful back deck for relaxing. Fast WiFi. High chair & pack ’n play available. Weekly/monthly discounts! Please enter exact guest count when booking!

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.

4.93 out of 5 average rating, 223 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.

4.84 out of 5 average rating, 49 reviews

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

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.

4.99 out of 5 average rating, 143 reviews

An inviting lofted sleeping area features a spacious bed flanked by bedside tables with softly glowing lamps. Delicate string lights create a warm ambiance across the sloped ceiling, while a patterned area rug adds comfort underfoot.

Tiny home in Headland

Home in Heart of Headland

Quaint cottage located on the grounds of the beautiful and historical Covington Home that was built in 1902. Headland, AL better known as the “Gem of the Wiregrass” was rated one of the safest cities in AL in 2019 and is a designated Main Street community. The cottage is walking distance to the square where you will find soft music playing as you stroll the streets, picturesque oak trees, stylish boutiques and cuisine to fit any taste pallet. It is less than 10 miles to the Dothan Airport.

A well-furnished living room features two comfortable sofas adorned with decorative pillows. A coffee table stands centrally, complemented by two lamps providing soft lighting. A television is positioned on an adjacent wall, and a single armchair adds additional seating. Natural light enters from the window, covered by light curtains.

4.83 out of 5 average rating, 107 reviews

Just Simply Convenient

This 3/2 home is convenient to most major shopping centers and movie theaters. Great restaurants and Winn Dixie/Publix grocery stores are within 5 min. Westgate park is a 7 min drive. We provide WiFi and Roku TVs in den & all bedrooms. We also provide individually wrapped bath soap, dishwasher powder, laundry detergent and fabric softener that should be enough for short stays and a nice starter for extended stays. Keurig and a standard coffee pot is provided along with a variety of K-cups.

A comfortable living area is depicted, featuring two plush sofas with decorative pillows. A small wooden table is positioned between them, alongside a potted plant. Two abstract artworks hang on the wall, and soft lighting creates a cozy ambience.

5.0 out of 5 average rating, 45 reviews

The Miller's Retreat

Welcome to your home away from home! This cozy, fully furnished house is ideal for travel nurses, health care professionals, medical college students, family, or anyone looking for comfort and convenience. It is conveniently located just 1.8 miles from Southeast Heath Medical Center and 3.3 miles from the Alabama College of Osteopathic Medicine. Farley Nuclear Plant is 18.5 miles. And before you start your day, 7Brew,, Chick-fil-A and many other restaurants are located within the area.

4.88 out of 5 average rating, 32 reviews

Hailey's Retreat 3/2 Cozy & Spacious Home +Sunroom

Welcome to Hailey's Retreat - A spacious and inviting home in the heart of Dothan! We are dedicated to providing you with a comfortable and renewing space during your vacation or work travel! We welcome corporate and contract work stays, family trips. 50" SMART TV in the living room, dedicated workspace and large living areas. 2.5 miles to Downtown Dothan, 1 mile to Southeast Health, 7 miles to Flowers Hospital, 6.5 miles to National Peanut Festival and more! **WEEKLY DISCOUNT AVAILABLE**

An inviting living area features a comfortable arrangement of plush seating around a cozy fireplace. A smart TV is mounted on the wall above the fireplace, while tasteful artwork adorns the walls. Light wood flooring complements the soft color palette throughout the space.

5.0 out of 5 average rating, 31 reviews

3BD Restorative Retreat - Fire Pit, Putting Green

Couples, girl's spa night, remote workers and traveling professionals - discover your ideal stay in Dothan’s Garden District. This colorful, health-focused oasis offers rest, focus, and comfort. Sip morning coffee on the deck or unwind in luxury bedding after a productive day. A serene, distraction-free space for those who value peace. RTJ Golf Trail (<6 mi) Dothan Country Club (0.7 mi) AL College of Osteopathic Medicine (<6 mi) Southeast Health & Flowers Hospital (<4 mi)