Vacation rentals in Headland

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.

5 out of 5 average rating, 16 reviews

Cozy and Comfy Retreat in a Quiet Neighborhood

JimRating, 5 stars3 weeks ago

We were able to check in late (3am) and very responsive to any requests. We were working 12 hr night shifts at the Farley Generating station. Marisol went the extra mile in providing a dinner for our crew because she knew how tough that schedule was. We had the most productive shift after eating a home cooked meal! Thank You, Marisol We will book again if returning to the area.

5 out of 5 average rating, 5 reviews

Home in Enterprise

The Luxury Townhouse II

AlyssaRating, 5 stars2 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!

4.89 out of 5 average rating, 231 reviews

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

Come Chill at our Cute 2 bedroom Cottage

KariRating, 5 stars6 days 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.

5 out of 5 average rating, 144 reviews

A spacious living area is shown, featuring a comfortable beige sofa adorned with several decorative pillows. A coffee table sits in front, complemented by a patterned area rug. A large TV mounted on the wall displays content, with soft natural light coming through the windows.

Home in Enterprise

Sleeps 10 I Pet-friendly I Mins to Novosel

SusanneRating, 5 stars3 days 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!

4.99 out of 5 average rating, 110 reviews

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

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.

4.85 out of 5 average rating, 55 reviews

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

Peaceful cabin on the river amazing views & canoes

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!

4.9 out of 5 average rating, 137 reviews

An inviting entryway features a bright front door flanked by sidelights. Light wood flooring extends into the living area, complemented by a stylish console table and decorative elements. A column adds architectural interest, while natural light filters in through windows with blinds.

Home in Enterprise

The Short Final-We welcome pets!

MelissaRating, 5 stars3 months ago

We had a wonderful stay at Gina’s cozy three-bedroom home. The house was clean, thoughtfully decorated, and the living room couch was especially comfortable. The kitchen was well-equipped, and the quiet location was perfect for relaxing. Gina was a responsive and attentive host. Highly recommend!

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What guests are saying

Pearl's Cove - 3 min from Hwy 231S

5 out of 5 average rating, 22 reviews2 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.

Home in Ozark

What guests are saying

Charming 2 bedroom

4.9 out of 5 average rating, 10 reviews6 months ago

Emily's place is in a safe, historic neighborhood. The town is within 5 minutes. The house has nice decor and is very spacious with lots of natural light. The kitchen is stocked to cook meals. Both bathrooms are comfortable sizes, one with shower, other with tub. The bedrooms were cozy and good sizes. The office room is a quiet and secluded. The extra living rooms are a delight. The washer and dryer are in a room with a sink. There's a drive in concrete carport with an outside patio pad with furniture. My family and I would book again if in the area!

Home in Dothan

What guests are saying

Southside Shanty

4.96 out of 5 average rating, 46 reviews3 days ago

The place was cute, clean, and exactly as described. 4 of us stayed and did a lot of cooking. The kitchen had everything we needed and MORE! Would definitely recommend to anyone. It's just far enough from town to not be busy, but still close enough for a quick trip to any store we needed. The host, Kelly, was always very friendly and responsive leading up to our stay and over the weekend. ☆☆☆☆☆☆

Home in Dothan

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Popular amenities for Headland vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Headland

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.

4.92 out of 5 average rating, 53 reviews

Stay Cozy: desirable location, near hospital/golf

AmandaRating, 5 stars4 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!

4.96 out of 5 average rating, 23 reviews

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

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.

4.95 out of 5 average rating, 80 reviews

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

Barndo“mini”um

JulieRating, 5 stars4 days ago

My second visit! Everything was great! Molly is a fantastic host! Very peaceful and will definitely return! Place is so clean and bed is awesome! Thank you!

4.93 out of 5 average rating, 30 reviews

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

Country living

BeckyRating, 5 stars4 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.

4.88 out of 5 average rating, 56 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

AnnaRating, 5 stars1 month ago

Mrs. Debbie was amazing. I was so thankful to have a sweet little getaway for my husband and I as we waited to attend a wedding. She was very accommodating and her animals were a perfect touch. Thank you Mrs. Debbie for an awesome experience.

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.

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.