Holiday rentals in Headland

5 out of 5 average rating, 53 reviews

Home in Headland

Dixieland Delight

BRAND NEW 2bed/2 bath peaceful getaway in the heart of historic and charming Headland, AL! Open-concept living area. Ample seating and a large flat-screen TV! 2 bedrooms and 2 full baths. The master bedroom offers a king-sized bed and an en-suite bathroom. The 2nd bedroom has a full-sized bed and an additional bathroom is conveniently located in the hallway. Explore charming downtown Headland, visit the nearby Headland Square, or head into Dothan for shopping, restaurants, and entertainment.

Superhost

Townhouse in Dothan

4.85 out of 5 average rating, 155 reviews

Stay & Play w Gameroom 2BR/2.5BA Short & Long Term

This 2 story townhome, over 1,400 sq ft, sleeps 6 and is centrally located in Dothan, AL with multiple parking. Located 5 minutes from hospitals, RTJ+DCC golf courses, Westgate Recreation Park and area shopping and restaurants. Keyless entry for self check-in. Newly renovated and fully equipped kitchen with new stainless steel appliances, granite, washer/dryer, fast/free wifi & more. Enjoy in home gameroom with 6ft. pool table, ping pong, ring toss & more. Long & short term stays are welcome!

4.95 out of 5 average rating, 130 reviews

Guest house in Dothan

State Park Cottage - Quiet Yet Centrally Located

Cottage is in the middle of a 2 1/2 acre wooded lot. It is in the middle of town, but your stay will be quiet and private. The neighborhood park, Solomon Park, is just one block away. Neighborhood is great for a stroll or run. You will be a short car ride from more than a dozen places to eat, grocery stores and shopping. We live on the property, but the cottage is a detached structure. If you need anything at all, we will be close by to provide as much or as little assistance as need

4.99 out of 5 average rating, 117 reviews

Tiny home in Headland

Home in Heart of Headland

Quaint cottage located on the grounds of the beautiful and historical Covington Home that was built in 1902. Headland, AL better known as the “Gem of the Wiregrass” was rated one of the safest cities in AL in 2019 and is a designated Main Street community. The cottage is walking distance to the square where you will find soft music playing as you stroll the streets, picturesque oak trees, stylish boutiques and cuisine to fit any taste pallet. It is less than 10 miles to the Dothan Airport.

4.93 out of 5 average rating, 144 reviews

Twin Pines | Luxury Getaway

Welcome to Dothan's Gem! A beautifully designed dream home! Bringing the whole family? Working remotely? Rest assured, you'll have high speed internet no matter what, with speeds up to 500mbps! While there's plenty of privacy, this location makes it easy for you to get around You are only: 4 mins to Flower's Hospital 5 mins to Westgate Recreation Park 5 mins to Forever Wild Trails 10 mins to the heart of Downtown Dothan 1.5 hrs to PCB & surrounded by Dothan's best restaurants!

4.95 out of 5 average rating, 255 reviews

Cottage in Dothan

The Oak Nest Garden District

Our cozy cottage home is 900 square feet and it is located behind our home in the beautiful garden district-a quiet, peaceful neighborhood. This adorable cottage has a full, spacious kitchen(sink, refrigerator,stove/oven, microwave, dishwasher basic cooking needs),living room, dining room, bar seating,bedroom with a queen-sized bed, walk-in closet, and stack unit washer/dryer. We are convenient to ACOM and 30 minutes to Fort Rucker. There are 2 nearby parks as well as hospitals.

5 out of 5 average rating, 113 reviews

Townhouse in Dothan

Special Rates For Summer! Chadwick Townhouse

Experience the best of Dothan in this stylishly renovated townhome. Perfectly situated for adventure, you're just moments from championship golf at RJT and DCC, thrilling water fun at Water World, exciting games at the Westgate Baseball and Tennis Complex, the serene beauty of Forever Wild trails, and conveniently close to both area hospitals. Unwind in comfort with a fully equipped kitchen, perfect for whipping up delicious meals and stay connected with blazing-fast Wi-Fi.

4.99 out of 5 average rating, 195 reviews

Cottage in Dothan

Juju’s Pond House on Smith Pond

Take it easy at this unique and tranquil getaway located on 100 acres and nestled quietly on a private pond. The house was originally built in 1921 and in 2018 we had the house moved down to the pond and did a full renovation while preserving as much original character as we could. Enjoy your morning coffee and watch the sunrise from the screen porch swing or one of the docks at the pond. The property has nature trails to explore, fishing, and plenty of wildlife.

4.98 out of 5 average rating, 64 reviews

The Copper Door Cottage*No Cleaning Fee*

Excellent central location! Minutes to downtown Dothan. Plant Farley 30 min away. Just an hour & 25 min drive to beautiful PCB. Quiet and quaint neighborhood. Cozy, simple, and family friendly home with everything you need! SUPER comfy beds including a king DReAMCLoUD and a queen BEaUtySLeEp! Super HIGH SPEED FIBER OPTIC INTERNET. A 55” smart tv in the living room and a 32” smart tv in the king bedroom! Make yourself at home! Excellent communication with Host.

5 out of 5 average rating, 131 reviews

Elegant house in the Heart of Dothan

Whether you are in Dothan for work or visiting, we hope you will enjoy your accommodation in our comfortable spacious house! You will find an open living area, well equipped kitchen, three bathrooms, and three bedrooms with comfortable king and queen size beds. The house also has high speed internet and two Smart Roku TVs for your work or entertainment. Please, remember, we can host max 6 guests. No visitors allowed. No family meetings or gatherings.

4.91 out of 5 average rating, 450 reviews

Flat in Dothan

Claire’s Cottage with privacy gate

Everything you need in a quaint, modern space located on 7 secluded acres with a privacy gate only minutes from the Ross Clark Circle and downtown, Wi-Fi, Smart TV with YouTube TV subscription included (over 70 channels), brand new fridge, spacious rooms. Washer and dryer available. We allow pets on a case by case basis and charge a one time $10 fee per pet upon guests arrival. We also offer EV level 2 charging (40 amp) for a flat $10 fee.

4.92 out of 5 average rating, 118 reviews

Home in Columbia

The Blackshear Place

A 100 year old house on land that was homesteaded in the 1800’s. Plenty of character, peaceful, private and quiet. 18 minutes from Ross Clark Circle, Dothan Al., 15 minutes from Headland Al. 19 minutes from Blakely Ga. 15 minutes to Log Cabin Restaurant in Georgia and Huggin Molly’s in Abbeville Al. Nearest grocery and gas is 10 minutes in Columbia Al. No WIFI hot spots work well Verizon tower 2 miles away

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Other great holiday rentals in Headland

4.96 out of 5 average rating, 67 reviews

The Hidden Gem

ElizabethRating, 5 stars2 weeks ago

This house was wonderful! It was so private and quiet. The home was clean and the beds were comfortable. The decor was amazing. We would stay here again and again!

5 out of 5 average rating, 6 reviews

Farm stay in Ashford

Cozy Catalina RV Home

SoteraRating, 5 stars12 months ago

Stayed 2 weeks and was a great stay both weeks. very clean and close to my job. Very cheap and worth every bit of money. Sue was very friendly and if I needed anything, she was there to help with all my needs.

5 out of 5 average rating, 9 reviews

Sedona Hideaway 3/2 Dothan, Alabama

Lisa and Michael Rating, 5 stars1 month ago

Vanita is always a great host. The house is always clean and comfortable. Responsive and proactive! Will continue to book with them!

4.99 out of 5 average rating, 75 reviews

Loft in Headland

Downtown Main St. Gem - Loft 5

GentryRating, 5 stars2 weeks ago

I really enjoyed my stay! The loft is very cozy and relaxing. Melissa was very attentive. Tye ceiling in the bedroom is lower but I didn't notice have an issue being an average size man in height, thus I did not bump my head on those old beams. I highly recommend staying here, you will not be disappointed!

5 out of 5 average rating, 8 reviews

Great Dothan location

KyleeRating, 5 stars1 week ago

We’ve stayed at both of Eric’s properties, and this one was our favorite! The location was perfect—close to everything we wanted to do. The house itself was spacious, comfortable, and had everything we needed for a great stay. Eric is always a fantastic host—responsive and thoughtful. Highly recommend!

4.93 out of 5 average rating, 43 reviews

Home in Headland

Cozy Cottage

TammyRating, 5 stars3 days ago

We absolutely adored the cozy cottage! It was the perfect place for our weekend getaway! We needed the peacefulness and relaxing environment it gave us. I would highly recommend it.