Holiday houses in Headland

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Top-rated holiday rentals in Headland

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Guest favourite

Guesthouse in Dothan

4.95 out of 5 average rating, 124 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.

Guest favourite

Home in Dothan

4.96 out of 5 average rating, 152 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.

Guest favourite

Guest suite in Enterprise

4.98 out of 5 average rating, 524 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 favourite

Townhouse in Dothan

4.79 out of 5 average rating, 133 reviews

Quiet & Comfy ~ 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 favourite

Home in Headland

4.92 out of 5 average rating, 142 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.

Guest favourite

Townhouse in Headland

4.98 out of 5 average rating, 270 reviews

Courtyard Headland

Cozy 800 sq ft apartment located off the square in Headland. Former commercial property converted to residential in the late 90's, this unique space has a gated courtyard in the front & additional gated outdoor living in the rear. Guests often describe it as having a "Savannah" feel. A quiet community & steps away from a park, quaint shops, restaurants and a police station. Located 10 minutes from Dothan, Headland offers a quiet & safe small town atmosphere convenient for commuters

Guest favourite

Home in Dothan

4.95 out of 5 average rating, 115 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!

Guest favourite

Cottage in Dothan

4.96 out of 5 average rating, 247 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.

Guest favourite

Cottage in Dothan

4.99 out of 5 average rating, 171 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.

Guest favourite

Home in Dothan

5 out of 5 average rating, 120 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.

Guest favourite

Rental unit in Dothan

4.92 out of 5 average rating, 400 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

Home in Columbia

4.92 out of 5 average rating, 112 reviews

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