Vacation rentals in Headland

4.95 out of 5 average rating, 128 reviews

Guesthouse in Dothan

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 needed.

5 out of 5 average rating, 51 reviews

A coffee station is presented with a Keurig machine beside a decorative mug that states a welcoming message. The setup is placed on a marble countertop, complemented by a small wooden trivet, creating a functional yet charming space for morning brews.

Home in Headland

Dixieland Delight

BRAND NEW 2bed/2 bath 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.

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.

4.97 out of 5 average rating, 172 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.

Guest suite in Enterprise

A close-up of a striped chicken stands prominently in the foreground, showcasing its vibrant red comb and vivid orange eye. In the background, additional chickens can be seen foraging in a natural setting, surrounded by greenery and straw.

4.98 out of 5 average rating, 556 reviews

BEST VALUE - No Cleaning Fee

"Relaxing, calm, quiet, peaceful"--all used to describe the 1,200 sq. feet of guest space attached to our home--Read a complete description under "The Space." The private guest suite includes a family room, two bedrooms and bath on our micro-farm just 4 minutes from Fort Rucker and Enterprise. Southern hospitality at its best--Read our reviews! Ammenities include personal-size fridge, coffee, microwave, pool table, WiFi, TV, DVD, Wii, games and toys; laundry room; Handicap/ADA accessible;

4.99 out of 5 average rating, 115 reviews

The cottage is framed by well-maintained shrubs and trees, with a gravel path leading to a sitting area with a bench. The building features a metal roof and a charming exterior, surrounded by a grassy area and a white picket fence in the background.

Tiny home in Headland

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.

A spacious single-story home showcases a modern design, featuring a light-colored brick exterior and dark brown garage doors. The front yard is adorned with manicured grass, while large windows allow natural light to enter. Tall trees frame the property, enhancing its serene setting.

4.93 out of 5 average rating, 144 reviews

Twin Pines | Luxury Getaway

Welcome to Dothan's Gem! A beautifully designed dream home! Bringing the whole family? Working remotely? Rest assured, you'll have high speed internet no matter what, with speeds up to 500mbps! While there's plenty of privacy, this location makes it easy for you to get around You are only: 4 mins to Flower's Hospital 5 mins to Westgate Recreation Park 5 mins to Forever Wild Trails 10 mins to the heart of Downtown Dothan 1.5 hrs to PCB & surrounded by Dothan's best restaurants!

4.95 out of 5 average rating, 255 reviews

A spacious dining area features a large wooden table surrounded by two long benches. A chessboard set with glass pieces is displayed on the table. Natural light streams in through a large window, complemented by soft curtain panels.

Cottage in Dothan

The Oak Nest Garden District

Our cozy cottage home is 900 square feet and it is located behind our home in the beautiful garden district-a quiet, peaceful neighborhood. This adorable cottage has a full, spacious kitchen(sink, refrigerator,stove/oven, microwave, dishwasher basic cooking needs),living room, dining room, bar seating,bedroom with a queen-sized bed, walk-in closet, and stack unit washer/dryer. We are convenient to ACOM and 30 minutes to Fort Rucker. There are 2 nearby parks as well as hospitals.

5 out of 5 average rating, 113 reviews

A warm living area features a cozy sectional sofa in a light tan color. A circular clock decorates the wooden wall above a white brick fireplace. A neutral area rug lies beneath a coffee table adorned with a small plant. Dining tables are visible in the background.

Townhouse in Dothan

Special Rates For Summer! 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.

4.99 out of 5 average rating, 194 reviews

A screened porch features a cozy seating area with a cushioned sofa, offering views of a serene pond surrounded by greenery. Large windows provide an unobstructed view of the tranquil landscape, reflecting the calm water and tree line.

Cottage in Dothan

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.

4.91 out of 5 average rating, 450 reviews

A serene outdoor scene captures a donkey in the foreground, with lush green grass and trees surrounding a spacious pasture. In the background, several horses graze peacefully, framed by a clear blue sky filled with scattered clouds.

Apartment in Dothan

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.

4.92 out of 5 average rating, 118 reviews

The bathroom features green walls and a natural wood vanity with a basin sink. It includes a toilet, shower/tub combination, and two round mirrors above the vanity. A window with light drapes allows natural light, while towels and toiletries are neatly arranged on the counter.

Home in Columbia

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

4.98 out of 5 average rating, 144 reviews

The entrance features a wooden deck with a dark canopy overhead. Brightly painted planters stand on either side of a red bench, adding color to the inviting entryway. White doors with an x-pattern and black lanterns complete the charming facade.

Tiny home in Slocomb

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 spacious kitchen has new appliances. 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.

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Popular amenities for Headland vacation rentals

Self check-in

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BBQ grill

Laptop-friendly workspace

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Other great vacation rentals in Headland

4.97 out of 5 average rating, 29 reviews

Your Home Away from Home

RichardRating, 5 stars3 days ago

We stayed here last year for a week with a smaller dog and were impressed enough with Terry and the house to reserve it again on a return trip! Everything was in great shape and we were particularly impressed with the upgrades in the kitchen! We would stay there again with no hesitation!

5 out of 5 average rating, 6 reviews

A classic house is set amidst lush greenery, featuring a red exterior and a slate roof. Three gabled windows adorn the front, while a welcoming porch is lined with two chairs. Expansive lawns create a serene rural backdrop.

Farm stay in Ashford

Cozy Catalina RV Home

SoteraRating, 5 stars12 months ago

Stayed 2 weeks and was a great stay both weeks. very clean and close to my job. Very cheap and worth every bit of money. Sue was very friendly and if I needed anything, she was there to help with all my needs.

4.89 out of 5 average rating, 61 reviews

A charming porch features a small round table and two white chairs, surrounded by potted plants. The entrance, framed by wood beams, leads to a door with a window above it, providing a welcoming access point to the barn unit.

Barn in Slocomb

Zeke’s House: Bed & Barn Bliss

LeighRating, 5 stars5 days ago

Beautiful and peaceful place and Debbie is very kind and communicative. Also enjoyed seeing host interact with her animals - horses, dogs, & the sweetest cow - extraordinary experience in all ways.

The kitchen features white cabinetry and granite countertops, complemented by stainless steel appliances. Natural light filters through sheer curtains, illuminating the dining area with a wooden table and coordinating chairs. The space is open and organized, promoting a functional gathering area.

5 out of 5 average rating, 41 reviews

Garden District Hideaway, King Bed

WenxianRating, 5 stars1 month ago

Dora is a very nice and friendly host, who kept me closely informed about her place and our stay in Dothan. Her house is very clean and well maintained, everything is good and as we expected, we had thorough enjoyed our visit to AL and had a wonderful three-day stay at this lovely home, thank you so much Dora!

4.99 out of 5 average rating, 75 reviews

An open floor plan is highlighted, showcasing a stylish kitchen with modern appliances and a cozy living area. Exposed wooden beams add character to the ceiling. A staircase leads to a sleeping loft, providing additional space for relaxation.

Loft in Headland

Downtown Main St. Gem - Loft 5

GentryRating, 5 stars1 week ago

I really enjoyed my stay! The loft is very cozy and relaxing. Melissa was very attentive. Tye ceiling in the bedroom is lower but I didn't notice have an issue being an average size man in height, thus I did not bump my head on those old beams. I highly recommend staying here, you will not be disappointed!

A bright blue coffee maker is positioned on a granite countertop, accompanied by a tray containing several coffee pods, creamers, and sugar packets. A white mug sits ready for use, highlighting a convenient setup for guests to prepare their morning beverage.

4.78 out of 5 average rating, 113 reviews

Four bedroom home steps away from Westgate Park!

JonathanRating, 5 stars1 month ago

Great place to stay in a very quiet and safe neighborhood! Place was clean and had everything we needed for our short trip visiting family. Great location very close to restaurants and groceries. Amanda was a great host and very responsive!

A wooden deck with multiple levels is shown, leading up to a house with large windows. The light-colored siding of the building contrasts with the weathered wood of the deck. A door is positioned at the center, providing access to the interior.

5 out of 5 average rating, 18 reviews

Hannah's Cottage

MohammedRating, 5 stars1 month ago

Nice and clean house. Excellent host and easy to communicate.