Holiday rentals in Headland

Stay & Play w Gameroom 2BR/2.5BA Short & Long Term

This 2 story townhome, over 1,400 sq ft, sleeps 6 and is centrally located in Dothan, AL with multiple parking. Located 5 minutes from hospitals, RTJ+DCC golf courses, Westgate Recreation Park and area shopping and restaurants. Keyless entry for self check-in. Newly renovated and fully equipped kitchen with new stainless steel appliances, granite, washer/dryer, fast/free wifi & more. Enjoy in home gameroom with 6ft. pool table, ping pong, ring toss & more. Long & short term stays are welcome!

Downtown Private Suite *No Cleaning Fee*

Enjoy your very own private access into the home from the back patio into the private living room with a joined master bedroom and bathroom. This home is centrally located in downtown Enterprise only 12 minutes from the Enterprise Fort Novosel gate and 30 minutes to Dothan! *Please note this is a shared home, but none of the living spaces are shared. A locked door separates both halves of the home for your privacy*. No recreational drugs or smoking is allowed in the home or on the property.

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

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.

Summer Rate Special! Chadwick Townhouse

Experience the best of Dothan in this stylishly renovated townhome. Perfectly situated for adventure, you're 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 blazing-fast Wi-Fi.

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.

Comfortable Tiny House In Wicksburg

Comfortable tiny home in Wicksburg, Alabama offers a loft with a queen size bed. The downstairs has another sleeping area that includes a twin size sleeper sofa. The kitchen is spacious enough to make your favorite meal. There is a scenic view for a peaceful stay, but only about 1 hours drive from places like Panama City Beach Florida. Also, Dothan is 14 miles and Ft Novosol is 12 miles away. We also offer high speed Internet and free, unlimited wifi.

Barndo“mini”um

Peaceful, private country retreat with beautiful views and friendly cows in the backyard. Enjoy your morning coffee on the porch swing and relax in the ultra-comfy bed after a quiet, restful night. Includes full-sized fridge, microwave, toaster oven, TV, Wi-Fi, and full bathroom. Just 10 minutes from Farley Nuclear Plant and 13 minutes from Southeast Health. Perfect for relaxing stays or quiet work trips. Come enjoy our little slice of paradise!

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.