Holiday houses in Headland

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Top-rated holiday rentals in Headland

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Guest favourite
A comfortable living area features a plush green sofa facing a wooden entertainment unit with a large TV. A round coffee table sits on a woven rug, and natural light enters through a nearby window, illuminating the space's neutral tones.
Condo in Dothan
4.93 out of 5 average rating, 140 reviews

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!

Top Guest favourite
The open-concept living area features a light-filled space with ample seating, including a gray sofa and a plush armchair. A large flat-screen TV is mounted on a wooden media console against a white wall. Bright natural light filters through the nearby window dressed in sheer curtains.
Home in Headland
5 out of 5 average rating, 73 reviews

"Dixieland Delight". Entire Home- Newly Built!

Newly built 2bed/2bath 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.

Guest favourite
A serene bedroom features a spacious bed with a light blue coverlet, accented by dark pillows. A decorative throw lies across the edge. Soft curtains frame the window, while a dresser and bedside tables provide storage. A tufted bench adds additional seating.
Townhouse in Dothan
4.86 out of 5 average rating, 164 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!

Top Guest favourite
A spacious room is furnished with two beds, providing ample sleeping accommodations. A small dining table sits in the foreground, while a television and seating area are arranged against the wall. Natural light enters through multiple windows, creating a bright and airy environment.
Guesthouse in Dothan
4.96 out of 5 average rating, 134 reviews

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

Top Guest favourite
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
4.99 out of 5 average rating, 129 reviews

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.

Top Guest favourite
A serene bedroom features a spacious bed with a light-colored duvet and flanked by two nightstands. Natural light enters through the windows, complemented by soft curtains. A wall decor piece adds a subtle touch, while a fan above provides airflow.
Home in Dothan
5 out of 5 average rating, 48 reviews

Garden District Hideaway, King Bed

Forget your worries in this spacious and serene space. Centered in the popular Garden District, The Hideaway is just minutes from restaurants, shopping centers, and both hospitals (3 miles). The master bedroom features a king-sized bed with a DreamCloud mattress. Each bedroom features a Smart TV and ceiling fan. Kitchen includes basic essentials like coffee, sugar and spices. There is also a washer and dryer available for your use. *WE HAVE A NO PET POLICY DUE TO ALLERGIES*

Top Guest favourite
Home in Dothan
5 out of 5 average rating, 100 reviews

Hank’s Place - CLEAN•Comfortable•Family Stays

Welcome to Hank’s Place! We’re so glad you’re here! When you choose to stay with us, you partner with us in helping to provide clean, safe housing for families in medical crises, as a large part of our profits are used to fund housing for families who are in need of a temporary place to stay due to serious medical situations. Located 1 mile from Southeast Health and 7 miles from Flowers Hospital. Short term or executive professional/corporate midterm, we’ve got you covered.

Top Guest favourite
Townhouse in Dothan
5 out of 5 average rating, 138 reviews

Renovated Townhome With Sunroom

Experience the best of Dothan in this stylishly renovated townhome. Perfectly situated for adventure, 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 the blazing-fast Wi-Fi.

Top Guest favourite
A wooden swing is suspended from a sturdy tree branch, overlooking a peaceful pond surrounded by lush greenery. The water reflects the clear blue sky, and the distant tree line creates a serene backdrop, inviting relaxation and contemplation.
Cottage in Dothan
4.99 out of 5 average rating, 215 reviews

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.

Top Guest favourite
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
4.95 out of 5 average rating, 114 reviews

Barndo“mini”um

Peaceful, private country retreat with beautiful views and friendly cows in the backyard. Enjoy your morning coffee on the porch swing and relax in the ultra-comfy bed after a quiet, restful night. Includes full-sized fridge, microwave, toaster oven, TV, Wi-Fi, and full bathroom. Just 10 minutes from Farley Nuclear Plant and 13 minutes from Southeast Health. Perfect for relaxing stays or quiet work trips. Come enjoy our little slice of paradise!

Top Guest favourite
A softly colored bedroom features a spacious bed with a decorative quilt and a wooden headboard. Natural light streams in from large windows, illuminating the room. A sliding glass door leads to a private deck, adding to the bright and open feel of the space.
Apartment in Dothan
4.91 out of 5 average rating, 496 reviews

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.

Superhost
A spacious bedroom features a comfortable bed dressed in neutral-toned linens. Two bedside lamps provide soft lighting, and a neutral area rug adds warmth. A bathroom entry is visible in the rear, creating a functional layout for guests.
Apartment in Dothan
4.75 out of 5 average rating, 12 reviews

King Bed - Walk Downtown Dothan

Park your vehicle and walk everywhere in Downtown Dothan. Visit shops and restaurants. Two miles to Dothan Country Club, 2 miles to Southeast Health hospital, 5 miles to Alabama College of Osteopathic Medicine, 6 miles to Robert Trent Jones Highland Oaks. Guest has access to community pool! Fast Wifi, smart TV (with Youtube TV providing for live streaming). Fully stocked kitchen and bathrooms with all the essentials provided.

Popular amenities for Headland holiday rentals

  1. Airbnb
  2. United States
  3. Alabama
  4. Henry County
  5. Headland