House vacation rentals in Headland

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Top-rated house rentals in Headland

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Top guest favorite
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
5 out of 5 average rating, 88 reviews

"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.

Top guest favorite
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.
Home in Dothan
4.94 out of 5 average rating, 64 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!

Guest favorite
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.
Home in Dothan
4.93 out of 5 average rating, 212 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.

Top guest favorite
The spacious living room features a comfortable arrangement of neutral-toned sofas and a cozy chaise lounge, accented by decorative pillows. A light fixture hangs from the ceiling, and a large flat-screen TV is mounted above a gas fireplace. Natural light filters through a nearby window.
Home in Enterprise
4.99 out of 5 average rating, 111 reviews

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

Top guest favorite
A single-story home is presented with a combination of stone and brick exterior, framed by a neatly landscaped yard. Soft lighting highlights architectural features, while a vibrant sunset paints the sky in warm hues above.
Home in Enterprise
5 out of 5 average rating, 100 reviews

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.

Guest favorite
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.
Home in Dothan
4.83 out of 5 average rating, 104 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.

Top guest favorite
A spacious living room features a central fireplace framed by a wooden mantle. A large flat-screen TV is mounted on the wall opposite two comfortable gray sofas, accentuated by decorative pillows. A round coffee table sits on a patterned rug, with natural light illuminating the area from french doors.
Home in Enterprise
4.99 out of 5 average rating, 158 reviews

Perfect for Big Families, Sleeps 14, Fort Rucker A

Located in one of Enterprise, AL's finest neighborhoods, Cotton Creek, this 4 bedroom home offers an exceptional stay. With 3 King beds, 4 Full beds, 2 queen sleeper sofas, and 2 baths, it's ideal for larger families on a PCS or visiting Enterprise. Just minutes away from Fort Rucker, John Henderson Family Park, and the Enterprise Country Club. Enjoy the convenience of smart technology and security throughout the entire home, allowing you to unwind and make the most of your time.

Top guest favorite
A comfortable living area features a gray sofa adorned with decorative pillows. A ceiling fan provides air circulation. Nearby, a round dining table is surrounded by white chairs, and a lantern-style light hangs above. Natural light enters through a window draped with soft curtains.
Home in Dothan
5 out of 5 average rating, 100 reviews

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.

Guest favorite
The exterior of a modern home features a brown brick façade complemented by light-colored siding. A neatly trimmed lawn surrounds the driveway and entrance, which includes a decorative mailbox. The sky is partially cloudy, providing a soft natural light.
Home in Dothan
4.9 out of 5 average rating, 103 reviews

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!

Guest favorite
A spacious brick house is framed by a large green lawn, offering a welcoming facade. Low-maintenance landscaping is visible, with large windows on either side of the front door, allowing natural light to fill the interior.
Home in Kinsey
4.93 out of 5 average rating, 27 reviews

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.

Guest favorite
A century-old house is depicted, set on expansive grassland and partially shaded by surrounding trees. The structure features a welcoming front porch with steps leading up to a red door. Clear blue skies and scattered clouds provide a serene backdrop.
Home in Columbia
4.92 out of 5 average rating, 124 reviews

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

Top guest favorite
Home in Ozark
5 out of 5 average rating, 25 reviews

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.

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