
House vacation rentals in Headland
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Top-rated house rentals in Headland
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Headland house rentals
House rentals with a pool

Netty's Nest
we had a great stay, everything you need and an amazing host

Briarwood super nice 2BR/2.5 BA townhouse
The space was clean and well decorated. Was perfect for what we needed. Plenty of kitchen utensils to cook while we were there. Will stay again when we need to visit our son stationed at Fort Novosel.

L&B Property
very nice and clean I stay again

Spacious Townhome Retreat - Mins to Ft Novosel
Our second stay at Teresa’s place which was as expected. Great location for our needs to visit family at Ft Novotel and close to all Enterprise has to offer. Would stay again.

Baker’s Stay & Play
The host was so attentive and responsive in a very quick manner and the house was amazing so much fun my kids and I enjoyed it so much the fam had a BLAST ! Beautiful layout and so much to do in just one house and also the snacks and drinks that was left to us was such a great perk ❤️ definitely booking again and real soon 💕

Peaceful and Roomy Retreat
Nice place with good sized pool and a firepit. Nice quit neighborhood about 2 miles from walmart and several restaurants. Not our favorite place but would definitely stay again.

Beautiful Enterprise Condo
I couldn’t pick a better place to stay in. With Fort Novosel being so close, attending the graduation was a breeze. I will refer this place to all of my friends. 10/10 ⭐️

Beautiful 3BR 4bed/2.5 baths townhome
great host. perfect family stay for fort rucker visit.
Weekly house rentals

Stay Cozy: desirable location, near hospital/golf
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!

Mayberry on Main
We had a great stay! The house was clean, spacious, and had everything we needed. There was plenty of room for everyone, and we enjoyed the backyard area as well. The host was kind and very responsive, which made everything smooth from start to finish. We’d definitely recommend this place to others!

Funky, BOHO Chic Dothan Home
Great communication. Very easy check-out process. Plenty of space.

Sedona Hideaway 3/2 Dothan, Alabama
Vanita is always a great host. The house is always clean and comfortable. Responsive and proactive! Will continue to book with them!

Breezy Hill Retreat
Third year in a row staying here. Great location and quiet.

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

Great Kitchen, Double Garage - close to Westgate
We were very happy to find Rebecca and her very nice house as we evacuated from Hurricane Milton. A nice quiet and well located place that was clean and warmly decorated. The sunroom is nice additional feature to the home. We enjoyed our stay and enjoyed interacting with the people of Dothan, Al. Rebecca was very responsive and provided quick and courteous communications. Definitely will stay again with planning to be in Dothan, AL.

Saint Andrews’ Loft
Thank you Kerry. The place was exactly what I expected. Easy access and easy checkout. Right down the road from family and close to stores, restaurants, etc. Great communication and willing to help at any time. Nothing fancy but perfect for location and comfort. It was great having a washer and dryer. Look forward to revisiting in the future.
Private house rentals

The Owl and Magnolia-short and long term stays
The house was well kept and clean, the neighborhood was very quiet but convenient to downtown and other hot spots. We really enjoyed the city parks in Dothan. Jenie was very communicative and took our reservation last minute which helped our anxiety since we came to Dothan to escape Hurricane Milton. My girlfriend Jill loved being so close to a local yoga studio. I would recommend if you are looking for a quiet and relaxing spot in Dothan to live and work from while in the area.

Pearl's Cove - 3 min from Hwy 231S
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.

Your Home Away from Home
Terry was truly the best host. My stay was incredible and hated to leave. Dothan community is amazing. Thank you from the bottom of our hearts.

Home in the heart of Enterprise
Had everything we needed. Home was as described and was great for our visit.

Gazebo House
I rented both houses for the groomsmen of my son’s wedding. It was perfect! Kit was a wonderful, gracious host. I will definitely be renting again when I have family traveling from out of town.

Four bedroom home steps away from Westgate Park!
Great place to stay in a very quiet and safe neighborhood! Place was clean and had everything we needed for our short trip visiting family. Great location very close to restaurants and groceries. Amanda was a great host and very responsive!

Swann lake house
Awesome place. We fished a bass tournament on Lake Eufaula, and Bobby’s place exceeded all our wants and needs.

Sweet Home Alexander's
We were so grateful for a place to stay close to Fort Novosel at a great price! This was a great little neighborhood with a beautiful place to sit in the backyard .
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