Vacation rentals in Headland

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Headland

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Condo in Dothan

4.97 out of 5 average rating, 100 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!

Guest favorite

Home in Dothan

4.96 out of 5 average rating, 154 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.

Superhost

Townhouse in Dothan

4.79 out of 5 average rating, 168 reviews

Feeling Beachy ~ 3BR/3BA Short & Long Term Stay

This spacious 2 story townhome, over 1,500 sq ft, sleeps 8 and is centrally located in Dothan, AL with multiple parking options. Located 5 minutes from both hospitals, RTJ+DCC golf courses, Westgate Recreation Park & Water World with area shopping and restaurants close by. Keyless entry for self check-in. Newly renovated and fully equipped kitchen, washer/dryer, fast/free wifi and more. Enjoy streaming your favorite movies and shows with our Roku TV. Short term & long term stays are welcome!

Guest favorite

Home in Dothan

5 out of 5 average rating, 7 reviews

Sedona Hideaway 3/2 Dothan, Alabama

1200 Sf of newly renovated comfort space in a quiet area on a cul de sac located in Dothan, Al ..convenient to Flowers Hospital &Southeast Alabama Medical Center, Fort Novasel & the Nuclear Plant. Golfing is at Highlands Golf Club . Shopping is close by and only 90 miles from the beautiful panhandle beaches of Florida. Three bedrooms with one KING & one QUEEN size bed & one FULL. Also enjoy a cozy private back patio with privacy fence. Two parking spots. Wifi, utilities, $ a streaming TV.

Guest favorite

Tiny home in Headland

4.99 out of 5 average rating, 89 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.

Guest favorite

Home in Ozark

5 out of 5 average rating, 20 reviews

Pearl's Cove - 3 min from Hwy 231S

Pearl's Cove is great for a family, a group of friends, new or seasoned professionals, or a couple in need of a vacation or staycation. This home is equipped with a spacious kitchen, two living rooms, a large sunroom, four bedrooms, two and a half bathrooms, a covered front porch and a covered back patio, a laundry room with a washer and dryer and pantry overflow space, and a large backyard. Guests will find touches of wellness and love throughout the home with plenty of space for fun!

Guest favorite

Cottage in Blakely

4.97 out of 5 average rating, 38 reviews

Cottage in the Woods that Sleeps 10

Raven’s Rest is nestled on 3 wooded acres in Cedar Springs, Georgia, a stone’s throw from the historic town of Blakely and the majestic Chattahoochee River. This newly renovated 2-bedroom, 1-bunkroom, 1-bath, 1-outdoor shower, cottage comfortably sleeps 10 people. We cater to weekend hunter and outage worker groups, as well as families and executives. With few lodging options in our area, Raven’s Rest is a versatile property that can accommodate many different lodging needs.

Guest favorite

Home in Dothan

4.9 out of 5 average rating, 10 reviews

Cozy Spyglass Hideaway 3 BR 2 Bath

Discover serenity at this 3-bed, 2-bath retreat near Flowers Hospital and Highland Oaks Golf Course. Enjoy a spacious living area, fully equipped kitchen, and cozy bedrooms with plush bedding. Relax on the private patio or explore nearby attractions and dining options. Ideal for medical visits or leisure, this home offers comfort and convenience in a quiet neighborhood setting

Guest favorite

Tiny home in Slocomb

4.98 out of 5 average rating, 132 reviews

Comfortable Tiny House In Wicksburg

Comfortable tiny home in Wicksburg, Alabama offers a loft with a queen size bed. The downstairs has another sleeping area that includes a twin size sleeper sofa. The spacious kitchen has new appliances. There is a scenic view for a peaceful stay, but only about 1 hours drive from places like Panama City Beach Florida. Also, Dothan is 14 miles and Ft Rucker is 12 miles away.

Guest favorite

Home in Dothan

4.94 out of 5 average rating, 36 reviews

Southside Shanty

Outside the hustle & bustle of traffic, yet still close to everything! We are located: • 3 miles from James Oates Park • 4.5 miles from Southeast Health • 5.5 miles from ACOM • 8 miles from Flowers Hospital • 8 miles from Westgate Park/Tennis/BMX • 6.5 miles from Wiregrass Public Safety Center • 5 miles from center of town/courthouse • 28 miles from Fort Novosel

Guest favorite

Apartment in Enterprise

4.95 out of 5 average rating, 76 reviews

Very clean, spacious w/ a beautiful view

Located in a nice neighborhood, just outside Novesol gate in Enterprise. 6 minutes from Daleville, 25 minutes from Dothan, and 20 minutes from Ozark also 90 minutes from the beach. Please do not book if you want to party. This is a quiet neighborhood,thanks!