Holiday 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!

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.

Bridal Cottage at Adams Acres

Relax & unwind at the Adams Acres Bridal Cottage, where modern comfort meets countryside charm. 🛌 Features You’ll Love: • Comfortable king-size bed in private bedroom + pull-out queen bed in sitting area • Spacious sitting area and vanity stations for getting ready • Private bathroom with a rainfall shower. Just minutes from Dothan, Adams Acres Bridal Cottage offers peaceful mornings and stunning sunsets with a nearby park featuring a walking trail, pickle ball court & more

Hank’s Place - CLEAN•Comfortable•Family Stays

Welcome to Hank’s Place! We’re so glad you’re here! When you choose to stay with us, you partner with us in helping to provide clean, safe housing for families in medical crises, as a large part of our profits are used to fund housing for families who are in need of a temporary place to stay due to serious medical situations. Located 1 mile from Southeast Health and 7 miles from Flowers Hospital. Short term or executive professional/corporate midterm, we’ve got you covered.

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.

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.

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

Kudzu Cottage

Charming 2BR/1BA home in the heart of downtown Ozark! Walk to restaurants, shops, pickleball, nightlife & more. Features a king & queen bed, full kitchen, washer/dryer, Wi-Fi, and smart TVs. Relax on the back porch with party lights and enjoy peaceful views of kudzu-covered woods. Perfect for a cozy, convenient stay!

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.

Mercy Creek Ranch Bunkhouse

1 bedroom rustic bunkhouse on a working horse ranch perfect for couples or small family. This chraming retreat sleeps up to 4 guests and offers all the comforts you need for a peaceful country stay. Bunkhouse has fully equipped kitchen and full bathroom and a warm rustic interior.

The Cottage

Kick back and relax in this calm, stylish space. Country living just outside city limits of Ozark. Cottage is close to HWY 231 and is located 6 miles from Ft. Rucker Ozark gate . It is also located 3 miles from Walmart, grocery stores, local restaurants and downtown Ozark.