Headland Accommodations

New

Downtown Main St Gem -Studio/Loft 5

2 Guests 1 Bedroom 1 Bathroom

Couples Retreat Apartment

Fireplace/Heating
Air Conditioner
Internet

ZA R2,001/Night For 7 Nights ZA R14,011

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7.1

Very Good

(120 Reviews)

Econo Lodge Dothan West

301.39 ft² 14 Guests 68 Bedrooms 1 Bathroom

Family Friendly Cabin

Fireplace/Heating
Pool
Parking

ZA R822/Night For 7 Nights ZA R5,752

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Highly Rated

9.0

Exceptional

(182 Reviews)

stayAPT Suites Dothan

3 Guests 1 Bedroom 1 Bathroom

Family Friendly Apartment

Pet Friendly
Kitchen
Parking

ZA R1,849/Night For 7 Nights ZA R12,946

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Quiet Family Home in Headland w/Games & Yard

10.0

Exceptional

(1 Review)

Quiet Family Home in Headland w/Games & Yard

2340 ft² 6 Guests 3 Bedrooms 2 Bathrooms

Family Friendly House

Fireplace/Heating
Balcony/Terrace
Kitchen

ZA R2,768/Night For 7 Nights ZA R19,370

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New

Peaceful 3BR/2BA Hidden Lake Home Near ACOM w/WiFi

1603.82 ft² 8 Guests 3 Bedrooms 2 Bathrooms

House

Balcony/Terrace
View
Parking

ZA R2,442/Night For 7 Nights ZA R17,092

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Claire’s Cottage is located on 7 secluded acres with a coded privacy gate.

Highly Rated

10.0

Exceptional

(109 Reviews)

Claire’s Cottage is located on 7 secluded acres with a coded privacy gate.

700 ft² 4 Guests 1 Bedroom 1 Bathroom

Family Friendly Apartment

Fireplace/Heating
Balcony/Terrace
Pet Friendly

ZA R2,196/Night For 7 Nights ZA R15,371

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New

Tranquil Countryside Estate in Ashford

3003.13 ft² 8 Guests 1 Bedroom 3 Bathrooms

Free Cancellation House

Fireplace/Heating
Parking
Internet

ZA R3,867/Night For 7 Nights ZA R27,072

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10.0

Exceptional

(42 Reviews)

Peaceful 3BR/2BA Hidden Lake Home Near ACOM w/WiFi

1582 ft² 8 Guests 3 Bedrooms 2 Bathrooms

Family Friendly House

Fireplace/Heating
Balcony/Terrace
Kitchen

ZA R3,120/Night For 7 Nights ZA R21,845

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New

Quiet Family Home in Headland with Games and Yard

2335.77 ft² 6 Guests 1 Bedroom 2 Bathrooms

Free Cancellation House

Fireplace/Heating
Parking
Internet

ZA R3,611/Night For 7 Nights ZA R25,270

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CLOSE TO EVERYTHING! The Hidden Gem Dothan

10.0

Exceptional

(32 Reviews)

CLOSE TO EVERYTHING! The Hidden Gem Dothan

1140 ft² 5 Guests 3 Bedrooms 1 Bathroom

Family Friendly House

Fireplace/Heating
Balcony/Terrace
Kitchen

ZA R2,933/Night For 7 Nights ZA R20,534

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New

Cheerful 3 bedroom house with fireplace!

7 Guests 3 Bedrooms 2 Bathrooms

House

Parking
Air Conditioner
Internet

ZA R1,770/Night For 7 Nights ZA R12,389

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Newly remodeled. 5 mi to Dothan shopping. 3 mi to Dothan Airport.

10.0

Exceptional

(20 Reviews)

Newly remodeled. 5 mi to Dothan shopping. 3 mi to Dothan Airport.

5 Guests 3 Bedrooms 1 Bathroom

Family Friendly House

Fireplace/Heating
Pet Friendly
Kitchen

ZA R2,014/Night For 7 Nights ZA R14,093

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More Top-Rated Accommodations in Headland Area

Why Choose Rent By Owner for your Headland Accommodations?

What makes our Accommodations special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Headland

When should you plan your Accommodations stay?

To make the most of your stay, consider visiting during the shoulder seasons when this destination experiences pleasant weather and fewer crowds, allowing you to enjoy the region's tranquil charm while booking top-rated properties through RentByOwner.com.

Peak Season Highlights

Spring (March to May)

During spring, the area experiences pleasant weather and blooming landscapes, making it an ideal time to enjoy your stay. The region's comfortable temperatures attract visitors seeking outdoor activities and relaxation.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F

Summer (June to August)

The summer months see a rise in travelers eager to take advantage of warm weather and longer daylight hours. This season is perfect for outdoor exploration and experiencing the local climate at its hottest.

Average Temperature Daytime: 85°F to 90°F - Nighttime: 65°F to 70°F

Off-Season Highlights

Fall (September to November)

As temperatures cool down in fall, fewer visitors venture here, allowing you to enjoy a more peaceful getaway. The region’s vibrant autumn scenery enhances the tranquility of your stay.

Average Temperature Daytime: 70°F to 75°F - Nighttime: 45°F to 55°F

Winter (December to February)

During winter, the area sees the lowest visitor numbers, offering a quiet retreat. While temperatures are cooler, this season provides a cozy experience and opportunities for off-season exploration.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Headland

How to Book Your Headland Accommodations

What's our booking process?

Our platform allows you to browse a curated selection of accommodations. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Headland

More Top-Rated Accommodations in Headland Area

Common Accommodations Amenities

What amenities can you expect?

Our Accommodations are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

Fully-equipped kitchens with modern appliances
Comfortable living areas with flat-screen TVs
Free Wi-Fi for staying connected
Air conditioning and heating for year-round comfort
In-unit washers and dryers for convenience
Luxurious bedrooms with premium bedding
Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

Enjoy a spacious outdoor patio or deck perfect for relaxing and entertaining during your stay.
Take advantage of private or shared outdoor pools that provide a refreshing escape in warm weather.
Make the most of landscaped gardens or yards that add to the scenic charm of this region.
Utilize barbecue grills or outdoor kitchens for cooking al fresco with family and friends.
Explore nearby walking trails or nature paths directly accessible from your accommodations.
Access outdoor sports facilities such as basketball courts, tennis courts, or volleyball areas.
Relax by fire pits or outdoor fireplaces, ideal for cozy evenings under the stars in this area.

Top Attractions Around Headland

What attractions are nearby?

Nearby, you can explore a variety of outdoor activities such as fishing, boating, and hiking in this welcoming region, making it an ideal destination for those seeking to enjoy nature and relaxation just moments from your chosen Headland accommodations.

Family Activities

Headland City Park Enjoy a day outdoors with family-friendly amenities, playgrounds, and scenic walking trails in this local park.
Headland Community Pool Cool off and have fun swimming together at the area's community pool during warm weather months.
Headland Sports Complex Get active with sports activities and athletic fields that are perfect for family games and recreation.
Local Nature Trails Explore nearby nature trails offering easy hikes suitable for all ages, providing an adventurous outdoor experience.

Adult Activities

Headland Golf Course You can enjoy a relaxing day on the fairways at this local golf course, perfect for both beginners and seasoned players seeking a scenic round.
Walking Trails and Nature Parks Explore the area’s natural beauty by taking a stroll along well-maintained trails and exploring nearby parks that offer peaceful outdoor experiences.
Local Dining Experiences Indulge in regional flavors at various dining establishments, where you can savor Southern cuisine and fresh local ingredients.
Community Events and Festivals Check out the calendar for community gatherings or seasonal festivals that showcase the region's rich culture and friendly atmosphere.

Headland Travel Tips

How Can You Make the Most of Your Stay?

Explore local dining options: Take advantage of the area's charming eateries to enjoy authentic regional flavors during your stay.
Visit nearby outdoor spots: Discover scenic parks and nature areas that showcase the natural beauty of this destination.
Plan day trips around the region: Use this base to explore neighboring towns and attractions, enriching your overall experience.
Book accommodations early: Secure your ideal property in advance to ensure a seamless and stress-free visit to the area.

Transportation Options

Headland Municipal Airport Located nearby, this airport offers convenient regional flights and private aviation options for travelers visiting the area.
Interstate 85 A major highway running through the region, providing easy access by car to neighboring cities and attractions.
Local Taxi Services Several trusted taxi companies operate here, offering reliable transportation for short trips within and around the destination.
Rideshare Options Popular ridesharing services are available in the area, offering flexible and on-demand transportation for visitors staying in the region’s accommodations.

Local Customs Options

Southern Hospitality: You'll notice a warm, welcoming attitude that embodies the region’s friendly spirit when you visit here.
Local Festivals and Events: Participating in community festivals is a cherished tradition, offering authentic insights into the area's cultural heritage.
Food Traditions: Enjoy local cuisine that celebrates Southern flavors, often prepared with family recipes passed down through generations.
Respect for Nature: The community values outdoor activities and maintains a deep respect for the natural environment surrounding this destination.

Frequently Asked Questions about Headland Accommodations

1. What are the top Accommodations in Headland?

There are a lot of options in Headland. If you plan on staying in the Headland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Accommodations in Headland:

2. How many Accommodations are available in Headland?

Currently, the total number of properties listed by RBO in 2026 is over 55 in the Headland area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Accommodations in Headland. 

3. What is the cancellation policy for accommodations in this region?

Cancellation policies vary depending on the property listing. You should review the specific terms provided in the listing details or contact the property owner directly to understand refund options and any associated fees.

4. Are there any pet-friendly options available here?

Many listings offer pet-friendly accommodations, but availability depends on the individual property. Check the listing details or reach out to the owner to confirm if pets are welcome during your stay in this area.

5. How do I ensure I am booking a reliable and quality accommodation?

Look for listings with verified reviews, detailed descriptions, and clear photos. Additionally, contacting the property owner for more information can help you confirm the quality and suitability of the accommodations for your needs.

6. What amenities should I expect when staying here?

Amenities vary by property but often include essentials like Wi-Fi, air conditioning, and kitchen facilities. Review each listing carefully for specific features or contact the owner for clarification before booking.

7. Is there a minimum stay requirement for reservations?

Minimum stay requirements depend on the property and can differ between listings. Be sure to check the booking details or contact the owner directly to confirm the duration of your desired stay.