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

4.92 out of 5 average rating, 171 reviews

The LA (Lower Alabama) dream

EarlRating, 5 stars3 weeks ago

Scott is a great host. Internet issues beyond his control popped up and he jumped on it right away. The house is in a great location and always clean. Check in is a breeze and the check out directions are minimal. This is our go to place in the area when we visit family.

Superhost

Treehouse in Hartford

4.85 out of 5 average rating, 55 reviews

Peaceful cabin on the river amazing views & canoes

Christopher JRating, 5 stars1 month 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

Tiny home in Headland

4.99 out of 5 average rating, 110 reviews

Home in Heart of Headland

CarolineRating, 5 stars3 weeks 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

Townhouse in Enterprise

4.8 out of 5 average rating, 41 reviews

Great New Place to Stay for Families!

FahadRating, 5 stars1 month ago

Renting a townhouse from ALEX has been an outstanding experience. The property is spacious, modern, and beautifully furnished, offering both comfort and style. The fully equipped kitchen, cozy bedrooms, and well-maintained bathrooms add to the luxury. The townhouse includes high-speed internet, smart TVs, an in-unit washer and dryer, and excellent climate control. The outdoor spaces are peaceful and well-kept, making for a relaxing environment. ALEX’s service is exceptional—professional, responsive, and efficient. Maintenance and housekeeping are prompt, ensuring a hassle-free stay. Overall, ALEX provides a top-tier living experience, and I highly recommend their rentals.

Guest favorite

Home in Enterprise

4.9 out of 5 average rating, 137 reviews

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!

Top guest favorite

Home in Hartford

5 out of 5 average rating, 17 reviews

River Retreat in Geneva, Alabama

BellmontRating, 5 stars1 week ago

My husband and i spent a few days at River Retreat and had a great time. The house is very spacious, clean and furnished very well. We really liked having Dish TV in every room. It was a little windy and cool during our stay but we still spent most of our time on the large deck enjoying the beautiful peaceful river and view. If you want to sit, lay down, swing, watch tv, play pool it is all on the deck. We want to say thanks to Jason who was a great host and very helpful with everything, he even called and checked on us while we were there.

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Popular amenities for Headland vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Headland

Guest favorite

Home in Dothan

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!

Guest favorite

Home in Columbia

4.96 out of 5 average rating, 23 reviews

Green Acres Farmhouse

AmeliaRating, 5 stars4 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

Tiny home in Ashford

4.95 out of 5 average rating, 78 reviews

Barndo“mini”um

KamraRating, 5 stars4 weeks ago

This was an amazing area to just have a getaway from the every day hustle of life. It was nice sitting outside on the swing and watching the cows in the pasture along with the sunset. Bed was extremely comfortable. Felt just like a home away from home. I recommend to everyone!

Top guest favorite

Home in Cottonwood

4.97 out of 5 average rating, 29 reviews

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.

Guest favorite

Barn in Slocomb

4.87 out of 5 average rating, 55 reviews

Zeke’s House: Bed & Barn Bliss

AnnaRating, 5 stars2 weeks 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.

Guest favorite

Home in Geneva

4.94 out of 5 average rating, 31 reviews

*Stay Awhile*

HowardRating, 5 stars2 weeks ago

We had a blast! The house was very quiet. Blakely was great as well! A great experience!

Top guest favorite

Home in Dothan

5 out of 5 average rating, 16 reviews

Hannah's Cottage

JessicaRating, 5 stars3 weeks 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