Holiday rentals in Headland

4.96 out of 5 average rating, 113 reviews

Apartment in Dothan

Lux Living near Downtown Dothan & Hospitals

Welcome to this thoughtfully designed space that just finished construction! Remote work here is a breeze, with WiFi speeds of 550mbps. Extended stays welcome! While there's all the privacy you'll need, this location makes it easy for you to get around You are only: 6 mins to South East Medical Center 7 mins to the heart of Downtown Dothan 8 mins to the Alabama College of Osteopathic Medicine 13 mins to Westgate Park & Flowers Hospital 1.5 hrs to PCB & surrounded by endless local restaurants!

4.95 out of 5 average rating, 128 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 needed.

5 out of 5 average rating, 51 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, 154 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!

Guest suite in Enterprise

4.98 out of 5 average rating, 553 reviews

BEST VALUE - No Cleaning Fee

"Relaxing, calm, quiet, peaceful"--all used to describe the 1,200 sq. feet of guest space attached to our home--Read a complete description under "The Space." The private guest suite includes a family room, two bedrooms and bath on our micro-farm just 4 minutes from Fort Rucker and Enterprise. Southern hospitality at its best--Read our reviews! Ammenities include personal-size fridge, coffee, microwave, pool table, WiFi, TV, DVD, Wii, games and toys; laundry room; Handicap/ADA accessible;

4.99 out of 5 average rating, 114 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.

4.95 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, 194 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.

5 out of 5 average rating, 129 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, 449 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.

4.88 out of 5 average rating, 327 reviews

Farm stay in Hartford

Hartford Art Studio and Loft

This treasure is a stand alone art studio with a loft surrounded by beautiful lawn and gardens. The Studio is 45 feet (read close) to the house. There are agricultural fields on three sides. The artist, Beverly Mayfield, is now deceased, but has filled the studio with masterful paintings.

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Other great holiday rentals in Headland

4.96 out of 5 average rating, 28 reviews

Your Home Away from Home

JeffRating, 5 stars1 month ago

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.

4.67 out of 5 average rating, 126 reviews

Stunning & Spacious 4BR Home

JulieRating, 5 stars2 weeks ago

Great location on the West side of Dothan..all our wedding festivities were within three miles. lots of places to eat and groceries close by. Safe neighborhood with great enclosed backyard. Cute, open floor plan for the kitchen, dining and living room. Plenty of closet space and dressers. Older charm with modern updates, lots of beds and very functional with nice working air.

4.99 out of 5 average rating, 74 reviews

Loft in Headland

Downtown Main St. Gem - Loft 5

GentryRating, 5 stars6 days 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!

Superhost

4.9 out of 5 average rating, 59 reviews

Baker’s Stay & Play

MaureenRating, 5 stars5 days ago

This is my 2nd stay with the Baker's. They are great hosts and provide whatever accommodations they can for their guests. This particular home, my grandkids picked, and they loved it; they were the happiest beyond happy. Thank you for a great stay.

4.93 out of 5 average rating, 41 reviews

Home in Headland

Cozy Cottage

MargueriteRating, 5 stars2 weeks ago

Katherine’s place was perfect for our needs. It was easy to find and exactly as described. The beds were super comfortable and the bathrooms provided all the comforts of home. Katherine was open and friendly. She proactively answered all questions before I could ask. Her responses were prompt, usually within 30 minutes or less. I highly recommend this cozy cottage. I will definitely stay here again when I’m in the area. Thank you for a wonderful stay!

Tiny home in Columbia

4.95 out of 5 average rating, 21 reviews

Rustic 1-bedroom cabin with ATV/Hiking Trails

VeltonRating, 5 stars3 weeks ago

Loved the stay and the owner was very nice. Peaceful and quiet place to relax.

Hotel room in Dothan

4.64 out of 5 average rating, 209 reviews

BRAND NEW 1 BR with 2 Queen Beds, Full Kitchen

RhondaRating, 5 stars1 month ago

Great price and location for a last minute travel trip to Dothan ~ clean and quiet with a cute interior courtyard ~ will definitely stay again