Vacation rentals 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.

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!

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!

State Park Cottage - Quiet Yet Centrally Located

Cottage is in the middle of a 2 1/2 acre wooded lot. It is in the middle of town, but your stay will be quiet and private. The neighborhood park, Solomon Park, is just one block away. Neighborhood is great for a stroll or run. You will be a short car ride from more than a dozen places to eat, grocery stores and shopping. We live on the property, but the cottage is a detached structure. If you need anything at all, we will be close by to provide as much or as little assistance as need

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.

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.

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**

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!

Newly Renovated, 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.

Spacious 3BR/2BA | Minutes from Dothan

Quiet 3BR/2BA brick home in Kinsey, only 7 minutes from downtown Dothan. Over 1,800 sq. ft. with tall ceilings, driveway parking, and a 0.4-acre lot with plenty of outdoor space. Inside you’ll find fast Wi-Fi, TVs, a full kitchen, and washer/dryer for long stays. Perfect for families, travel nurses, and work crews seeking space and comfort in a safe subdivision near Southeast Health, Flowers Hospital, Fort Novosel, shopping, dining, and all local conveniences.

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.

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.