Vacation rentals in Headland

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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, 231 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

The outdoor area features a cleared space with a gravel fire pit, surrounded by meticulously maintained grassy grounds. Beyond, rows of bushes are visible under a blue sky dotted with clouds, creating a serene natural setting.

Guest suite in Enterprise

4.98 out of 5 average rating, 547 reviews

BEST VALUE - No Cleaning Fee

DeborahRating, 5 stars1 week ago

Wonderful place for a night’s sleep (or more) while on a trip. The relaxing atmosphere around the house was perfect. Coffee and muffins were very much appreciated before leaving the next morning. We wish we could have stayed longer.

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

A large back deck is set among trees, featuring multiple outdoor dining chairs and a patio heater. The deck is elevated, offering a view of the surrounding nature. A staircase connects the deck to the ground level, blending the indoor and outdoor spaces.

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, 19 reviews

Cozy and Comfy Retreat in a Quiet Neighborhood

TashaRating, 5 stars2 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 well-lit bathroom features a modern sink with a sleek faucet and a large mirror above it. The lighted mirror reflects the soft tones of the walls. To the left, a doorway leads to a spacious bedroom with a bed visible in the background.

Home in Ozark

5 out of 5 average rating, 22 reviews

Pearl's Cove - 3 min from Hwy 231S

KatrinaRating, 5 stars2 months ago

This is my second stay, If you’re looking for a place to stay in this area, here it is. The home is spacious, clean and convenient. The host Christina and Sophia are good people that go out of their way to make you feel comfortable and welcome. I appreciate all they did for us! We will be back.

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

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, 57 reviews

Zeke’s House: Bed & Barn Bliss

Alyssa Rating, 5 stars3 weeks ago

Great place! Small, but had everything that you would need. Love showing up to the cow and horses in front of the property. Debbie was very friendly and we got to say hello before we left.

Guest favorite

A modern townhome is presented, featuring a well-maintained exterior with a neatly landscaped front yard. The driveway leads to a single-car garage, framed by lush greenery on either side. A bright blue sky enhances the inviting appearance of the property.

Home in Enterprise

4.89 out of 5 average rating, 45 reviews

Spacious Townhome Retreat - Mins to Ft Novosel

ChandlerRating, 5 stars1 month ago

No way that you could complain about this host or stay! Everything was great! Thanks so much for having us!

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