House 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.

Family · Value · Indoor spaces

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.

Family · Value · Sleep quality

Lovely Residential Ranch Home with KING bed

Our "Home Sweet Home 2" is a beautifully decorated residential home. This home is 3 BR, 2 BA, two car garage with private fenced yard. It is located 2 miles from the Enterprise Fort Rucker gate. Master BR: 1 King bed, Smart TV 2nd BR: 1 Queen bed, Smart TV 3rd BR: 2 Twin beds Living Room: Spacious with 55" in Smart TV with all streaming apps, gas FP, Lounge chaise can sleep one small person. Family/kid games. Coffee Bar: Fully stocked Kitchen: Cookware, dinnerware, wine glasses Pet Friendly

Family · Value · Condition

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.

Location · Value · Hospitality

Relax at the Ridge | 4BR/3BA

Welcome to Relax at the Ridge. This home is conveniently located right outside Ft. Rucker (Faulkner Gate) and minutes from Downtown, and Johnny Henderson Park. lt is also only about an hour and half away from the world's most beautiful beaches, the Gulf of Mexico. With 4 bedrooms and 3 bathrooms, it has plenty of room for families visiting Enterprise. The entire home is exclusively yours to enjoy. Equipped with smart technology and enhanced security measures, this could be your perfect stay.

Family · Value · Laundry

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.

Value · Location · Comfort

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.

Value · Location · Amenities

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.

Location · Family · Decor

Peaceful 3BR/2BA Hidden Lake Home Near ACOM w/WiFi

Welcome to Dothan, Alabama, the Peanut Capital of the World! If you are looking for a comfy, convenient and spacious home to unwind, your search is over! This modern home at The Hidden Lake is a 10 min walk or 3 minute drive to ACOM! Close to SouthEast Hospital, plenty of restaurants, and located in one of the safest neighborhoods in Dothan. Complete with a stocked kitchen, multiple bedrooms and bathrooms, WiFi, Smart TV, and much more, this is the perfect home for you!

Location · Family · Decor

Daniel Digs - 3/2 - Comfy, Central, & Convenient

Relax in this inviting home with comfy seating, quality mattresses, ceiling fans throughout, and a remodeled master bath with a custom-tiled shower. Enjoy the large fenced yard, covered patio with seating, gas grill, and spacious laundry room. Parking for up to 4 vehicles, plus room for a boat, trailer, or camper. Perfect for families or work trips—comfortable, practical, and peaceful. Please enter the exact number of guests when booking.

Value · Family · Backyard

4BR Oasis w/ Pool & Pet Friendly -Rucker

Relax with the whole family at this peaceful retreat. This family-friendly home will be your private oasis conveniently located in Enterprise AL. Enjoy the pool and backyard featuring a grill and fire pit! The home features a full kitchen, living room with 55in TV, two bathrooms, and four bedrooms! Make this your home away from home while you enjoy what Enterprise has to offer! Only minutes away from Ft. Rucker!

Value · Family · Check-in

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

Location · Family · Backyard