Vacation rentals in Headland

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Headland

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Enterprise

5 out of 5 average rating, 5 reviews

The Luxury Townhouse II

AlyssaRating, 5 stars3 months ago

This Airbnb was our family's favorite by far! It was so clean, beautiful, and accommodating. The cleanliness was what stood out to me the most! It was such a well kept and pristine space. Richie and Katelin also were very helpful and easy to connect with. A fantastic Airbnb all-around!

Guest favorite

A comfortable living area features a spacious gray sofa with colorful accent pillows, positioned in front of a large television. Light streams in through wide windows, illuminating a geometric rug on the wooden floor. The open layout leads to a bright kitchen area visible in the background.

Cottage in Enterprise

4.89 out of 5 average rating, 232 reviews

Come Chill at our Cute 2 bedroom Cottage

KariRating, 5 stars2 weeks ago

We were so impressed that Monty and his family did most of the work on this house themselves. They did a great job—you can feel the love they put into it. Everything was in perfect working order, and it was an ideal location for our antiracist family genealogy reckoning. Monty was very welcoming and made it all easy. Thank you for a wonderful stay.

Top guest favorite

An inviting open-concept living space is presented, featuring a comfortable gray sofa facing a wooden coffee table. A patterned area rug lies beneath, while a ceiling fan provides illumination. In the background, a dining area with a large table is visible, along with large windows allowing natural light.

Home in Enterprise

5 out of 5 average rating, 144 reviews

Sleeps 10 I Pet-friendly I Mins to Novosel

SusanneRating, 5 stars2 weeks ago

Ivan's place was just what our family needed. It was a peaceful respite from all the busyness that we had going with the wedding that we were in town for. Ivan always responded immediately if we had any questions. We greatly enjoyed our stay!

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, 110 reviews

Home in Heart of Headland

CarolineRating, 5 stars1 month ago

It has to be one of my favorite stays. The details were so appreciated, from makeup towels to bedding for a pet! With the electric fireplace and the AC unit, I would recommend it for any time of year. Some highlights are the peace, privacy, safety, and a parking spot was a bonus! It has a lovely yard as well.

Superhost

The elevated structure is perched on stilts surrounded by trees, featuring a large deck accessible by sturdy steps. Canoes are stored beside a picnic table, with additional seating visible on the ground level, providing a serene outdoor space for relaxation.

Treehouse in Hartford

4.84 out of 5 average rating, 56 reviews

Peaceful river cabin kayaks and canoes. great view

Christopher JRating, 5 stars2 months ago

So many little “extras”, ie snacks, welcoming beers❤️, natural flowers in vase, charcoal, insect repellent, almost everything needed for cooking! They even had extra rice that we cooked up as we forgot a side for that evening! The place was a perfect peaceful getaway. The entire family loved it!

Top guest favorite

The entryway features a wooden console table with multiple drawers and a decorative woven basket. A round mirror is mounted above the table, which holds a welcome sign and potted plants. A door with a glass panel showcases intricate designs, inviting guests into the home.

Home in Dothan

5 out of 5 average rating, 20 reviews

Cozy and Comfy Retreat in a Quiet Neighborhood

TashaRating, 5 stars4 days ago

The house was exactly how it was described! I loved the back patio, just hated the windy rain started while we were out there. The way the kitchen was stocked was amazing. Most just have the bare minimum when it comes to dishes, cookware etc. But Marisol really made you feel like you were cooking at home with all the extras. Just missing seasonings, but that definitely would not take away from the awesomeness of our stay. Marisol accommodating all our needs including the need for a late check out at the last minute. Overall it was definitely a five star stay and I’m about to book for all the upcoming dates we will be in town so not to miss the booking here.

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Popular amenities for Headland vacation rentals

Laptop-friendly workspace

Other great vacation rentals in Headland

Guest favorite

A covered porch features wooden flooring and brick walls, creating a welcoming space. A round rug is placed beneath a black metal bench, which is accentuated by a cushioned seat. Natural light filters through the windows, enhancing the outdoor view.

Home in Dothan

4.92 out of 5 average rating, 53 reviews

Stay Cozy: desirable location, near hospital/golf

AmandaRating, 5 stars5 months ago

The home was clean and very cozy! It had everything we needed for our stay! Peyton (the host) was very kind, helpful, and responsive! We were visiting family, so we will definitely stay again when we return to Alabama!

Top guest favorite

A spacious farmhouse stands amidst a serene landscape, surrounded by manicured shrubbery. The structure features multiple peaks in the roofline and a welcoming front porch. An expansive lawn stretches in front, with tree branches reaching upward against a clear sky.

Home in Columbia

4.96 out of 5 average rating, 23 reviews

Green Acres Farmhouse

AmeliaRating, 5 stars5 months ago

Our second year staying in this Beautiful place!!! We are looking forward to stay there next year!!! Excellent People, amazing place.

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, 84 reviews

Barndo“mini”um

WadeRating, 5 stars2 days ago

Molly places was a great stay

Top guest favorite

The exterior of a single-story home is shown, featuring a front porch with wooden railing. The structure is surrounded by a spacious grassy area, with a few trees in the vicinity and partially cloudy skies overhead.

Home in Cottonwood

4.93 out of 5 average rating, 30 reviews

Country living

BeckyRating, 5 stars5 months ago

This home is located on several acres in a country setting and offers peace and tranquility. The nearest shopping is a mere 2 miles away. The home is comfortably furnished and met our needs.

Guest favorite

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

4.88 out of 5 average rating, 58 reviews

Zeke’s House: Bed & Barn Bliss

KennethRating, 5 stars2 weeks ago

Just an overall pleasant trip. I felt right at home and was always greated with a smile. Definitely coming back.

Top guest favorite

A modern bathroom features a dual-sink vanity with gray cabinetry and ample counter space. Bright lighting is provided by a stylish light fixture above the mirrors. The floor is covered with white and gray marbled tiles, enhancing the contemporary look, while a door leads to additional storage.

Home in Dothan

5 out of 5 average rating, 16 reviews

Hannah's Cottage

JessicaRating, 5 stars1 month ago

Very clean and comfortable home with lots of space for a family of 7 to spread out. we only stayed one night but it was very nice. We plan to stay again!

Superhost

A modern kitchen features white cabinetry complemented by a spacious quartz island. Transparent bar stools surround the island, while stainless steel appliances are positioned against the wall. Soft under-cabinet lighting illuminates the tiled backsplash, creating a bright and functional cooking area.

Home in Midland City

5 out of 5 average rating, 4 reviews

Spacious luxury home

ObaidRating, 5 stars5 months ago

Great host, very responsive.

Superhost

An outdoor seating area is covered by a canopy, featuring a large sectional sofa with soft cushions and striped accents. Low tables are positioned nearby, and soft lighting drapes overhead, creating an inviting space for relaxation.

Home in Dothan

4.9 out of 5 average rating, 50 reviews

Baker’s Stay & Play

KristenRating, 5 stars1 week ago

Sandra’s listing met all our expectations and more! A couple families stayed for a soccer tournament. This place is amazing for families especially with kids. Sandra is very responsive and so sweet! I highly recommend and will be booking again!

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Vacation rentals in Headland

Top-rated vacation rentals in Headland

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