Vacation rentals in Headland

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Top-rated vacation rentals in Headland

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Guest favorite

Guesthouse in Dothan

4.95 out of 5 average rating, 117 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 needed.

Jul 22 – 29

€ 87 per night

Guest favorite

Loft in Headland

5.0 out of 5 average rating, 53 reviews

Downtown Main St. Gem - Loft 5

Open the gate and transport from Main St to our hidden gem. Walking into the renovated historic building you will appreciate that you can slip away and quietly relax-tucked away from the world. You may choose to walk only steps to the 14 acre greenspace of the downtown square or take a short drive to Dothan for movies and entertainment. Charm is at your fingertips in this downtown lofty retreat for 2. Close to Farley Nuclear Plant, Southeast Health and Flowers hospitals. Come and stay a while.

Jan 3 – 10

€ 100 per night

Guest favorite

Home in Dothan

4.98 out of 5 average rating, 122 reviews

Comfy 3 bedroom house with hot tub and game room.

Relax and unwind in this space, or even come to work or play. You will have the entire 3 bedroom, 2 full bath house to yourselves. Equipped with washer/dryer, kitchen, hot tub, work space, Wi-Fi, and even a little bar with ping pong table & dartboard. This is our house we have been remodeling and use as our own little getaway on date night, it’s far from upscale fancy, but it is cozy and with a soak in the hot tub can even be romantic. Welcome gift provided, message with any special requests.

Jul 13 – 20

€ 148 per night

Guest favorite

Home in Headland

4.93 out of 5 average rating, 138 reviews

Rustic Farmhouse

1,512 square foot, nearly 100 year old rustic Farmhouse on 1 acre with large backyard located in Headland, AL within walking distance from town square with restaurants, quaint shops & nearby parks. Just a 5 minute commute to Dothan & 1.5 hour drive to the world's most beautiful beaches in Panama City Beach, FL. This house was built in 1929 and has the original hardwood floors. Most of the doors are original and the home has 12 foot ceilings. if you loved Grandma's house you will love this.

Dec 27 – Jan 3

€ 114 per night

Guest favorite

Guest suite in Enterprise

4.98 out of 5 average rating, 466 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;

Guest favorite

Tiny home in Headland

5.0 out of 5 average rating, 69 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.

Jul 3 – 10

€ 84 per night

Guest favorite

Cottage in Dothan

4.96 out of 5 average rating, 226 reviews

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.

Aug 10 – 17

€ 125 per night

Guest favorite

Cottage in Dothan

4.99 out of 5 average rating, 137 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.

May 16 – 23

€ 145 per night

Guest favorite

Home in Dothan

5.0 out of 5 average rating, 107 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.

May 21 – 28

€ 235 per night

Guest favorite

Home in Headland

5.0 out of 5 average rating, 15 reviews

Cozy Cottage

Need a quiet place to relax? Enjoy serenity and rural scenery in a small southern town. This two-bedroom, two-bathroom home has been completely renovated and is surrounded by farmland. Only five minutes from the town square and fifteen minutes from the larger city of Dothan, it is an ideal location for guests who want to be away from the city's bustle without being too far from town.

Nov 10 – 17

€ 138 per night

Guest favorite

Guesthouse in Dothan

5.0 out of 5 average rating, 24 reviews

Private, Peaceful Apartment in Quiet Neighborhood

A newly built garage apartment offering a quiet, clean and breathable space in a centralized location for an individual, couple or small family to stay while you visit Dothan. Minutes from Target, Starbucks and more. This is a new Airbnb and we’re excited to have you - we’re blessed to live in such a wonderful place and hope to share it with visitors or residents of Dothan.

Dec 25 – Jan 1

€ 90 per night

Guest favorite

Apartment in Dothan

4.92 out of 5 average rating, 354 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.

Jun 27 – Jul 4

€ 83 per night