Vacation rentals in Headland

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Top-rated vacation 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, 64 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

A spacious room is furnished with two beds, providing ample sleeping accommodations. A small dining table sits in the foreground, while a television and seating area are arranged against the wall. Natural light enters through multiple windows, creating a bright and airy environment.

Guesthouse in Dothan

4.95 out of 5 average rating, 132 reviews

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

Top guest favorite

A family room with a pool table in the foreground features a comfortable seating arrangement including a brown sofa and chair. Natural light enters through two windows, illuminating a cozy atmosphere, while decorative elements and a welcoming front door enhance the space.

Guest suite in Enterprise

4.98 out of 5 average rating, 589 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;

Top guest favorite

An inviting lofted sleeping area features a spacious bed flanked by bedside tables with softly glowing lamps. Delicate string lights create a warm ambiance across the sloped ceiling, while a patterned area rug adds comfort underfoot.

Tiny home in Headland

4.99 out of 5 average rating, 126 reviews

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.

Guest favorite

The townhouse exterior features a mix of light-colored siding and red brick accents. Large windows with decorative shutters are present on the upper level, while a secure garage door offers convenient parking. Landscaping includes neatly trimmed shrubs and a small tree.

Townhouse in Enterprise

4.97 out of 5 average rating, 124 reviews

Townhouse 2/Self Check-in/Convenient to Ft Rucker

This 2 bedroom 2 1/2 bath townhouse is conveniently located 5 minutes from Fort Novosel and just minutes from the shopping areas and restaurants in Enterprise Alabama. It's packed with amenities to include 3 large TVs and High-speed wireless internet. The kitchen has all the necessities; dinnerware, silverware, knives, pots and pans, toaster, Kurig coffee maker, and more. We pride ourselves in hosting a place that we would want to stay in that has comfortable beds, very clean, and safe.

Superhost

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.

Home in Dothan

4.91 out of 5 average rating, 151 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!

Top guest favorite

A spacious living area features a brown sofa and two blue armchairs arranged around a coffee table. A flat-screen television is mounted on the wall, adjacent to a fireplace with a wooden mantle. Natural light enters through window blinds, enhancing the room's inviting atmosphere.

Townhouse in Dothan

5 out of 5 average rating, 128 reviews

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.

Top guest favorite

A wooden swing is suspended from a sturdy tree branch, overlooking a peaceful pond surrounded by lush greenery. The water reflects the clear blue sky, and the distant tree line creates a serene backdrop, inviting relaxation and contemplation.

Cottage in Dothan

5 out of 5 average rating, 205 reviews

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.

Top guest favorite

A cozy living area showcases a brown sofa, positioned near a light-colored area rug. New kitchen appliances are visible in the background, with ample natural light streaming through a nearby window. A staircase leads to the loft, providing additional sleeping space.

Tiny home in Slocomb

4.97 out of 5 average rating, 151 reviews

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.

Top guest favorite

A wooden porch swing is suspended from a support beam, positioned to overlook an open field. A vibrant sunset fills the horizon, blending soft hues of pink and orange against a backdrop of trees. The tranquil landscape invites moments of relaxation.

Tiny home in Ashford

4.95 out of 5 average rating, 103 reviews

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!

Guest favorite

A softly colored bedroom features a spacious bed with a decorative quilt and a wooden headboard. Natural light streams in from large windows, illuminating the room. A sliding glass door leads to a private deck, adding to the bright and open feel of the space.

Apartment in Dothan

4.91 out of 5 average rating, 467 reviews

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.

Top guest favorite

A charming art studio is set among lush greenery, featuring a gabled roof and large windows that allow natural light to fill the interior. A stone pathway leads to a wooden bench positioned on a manicured lawn, surrounded by diverse foliage.

Farm stay in Hartford

4.89 out of 5 average rating, 335 reviews

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.