Best Vacation Homes in Headland
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
Air Conditioner
Internet
Child Friendly
Laundry
US $195/Night
7 Nights - US $1,367
Cabin
7.1(106 Reviews)
68 Bedrooms
1 Bath
14 Guests
301.39 ft²
Parking- Air Conditioner
- Internet
- Child Friendly
US $50/Night
7 Nights - US $351
US $123/Night
7 Nights - US $859
Cottage
9.6(16 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
Balcony/Terrace
Kitchen- Air Conditioner
US $133/Night
7 Nights - US $931
House
3 Bedrooms
2 Baths
8 Guests
1603.82 ft²
- Parking
- Balcony/Terrace
View- Air Conditioner
US $250/Night
7 Nights - US $1,752
House
10.0(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
2340 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $272/Night
7 Nights - US $1,904
Cottage
10.0(9 Reviews)
2 Bedrooms
2 Baths
6 Guests
Hot Tub- Parking
Pool
Ocean View
US $234/Night
7 Nights - US $1,636
Cottage
10.0(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Pool
- Kitchen
- Air Conditioner
- Internet
US $259/Night
7 Nights - US $1,813
Headland Luxury Rentals
New
House
3 Bedrooms
2 Baths
9 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $546/Night
7 Nights - US $3,819
House
10.0(13 Reviews)
3 Bedrooms
2 Baths
6 Guests
2000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $438/Night
7 Nights - US $3,065
House
9.8(8 Reviews)
4 Bedrooms
2 Baths
10 Guests
Private Pool- Pool
- Air Conditioner
- Internet
US $364/Night
7 Nights - US $2,549
House
7.4(3 Reviews)
3 Bedrooms
2 Baths
12 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $340/Night
7 Nights - US $2,379
House
4 Bedrooms
2 Baths
8 Guests
3000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $339/Night
7 Nights - US $2,374
House
9.6(24 Reviews)
3 Bedrooms
2 Baths
8 Guests
1564 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $293/Night
7 Nights - US $2,049
House
3 Bedrooms
2 Baths
6 Guests
- Air Conditioner
- Internet
Pet Friendly- Child Friendly
US $284/Night
7 Nights - US $1,989
House
10.0(11 Reviews)
3 Bedrooms
2 Baths
6 Guests
1650 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $277/Night
7 Nights - US $1,942
Headland Pet Friendly Vacation Rentals
Cottage
10.0(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
US $237/Night
7 Nights - US $1,661
Hotel
9.2(180 Reviews)
2 Baths
505.9 ft²
- Parking
- Air Conditioner
- Pet Friendly
- Child Friendly
US $119/Night
7 Nights - US $833
Apartment
9.2(217 Reviews)
1 Bedroom
1 Bath
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $119/Night
7 Nights - US $835
New
House
10.0(1 Review)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $261/Night
7 Nights - US $1,827
Hotel
9.2(77 Reviews)
3 Baths
398.27 ft²
Breakfast
EV Charge Station- Parking
- Balcony/Terrace
US $179/Night
7 Nights - US $1,253
House
9.6(12 Reviews)
3 Bedrooms
2 Baths
6 Guests
1700 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $275/Night
7 Nights - US $1,924
Apartment
10.0(119 Reviews)
1 Bedroom
1 Bath
4 Guests
700 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $124/Night
7 Nights - US $866
House
10.0(20 Reviews)
3 Bedrooms
1 Bath
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $140/Night
7 Nights - US $978
Headland Large Vacation Homes
House
7.8(13 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Private Pool
- Parking
- Pool
- Kitchen
US $198/Night
7 Nights - US $1,383
House
4.2(5 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $146/Night
7 Nights - US $1,025
Why Choose Rent By Owner for your Headland Vacation Rental Homes?
What makes our Vacation Rentals 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 Vacation Rentals stay?
Choosing the right time to visit here ensures you can enjoy the area's inviting climate and local events, making your stay in this destination truly memorable with the perfect vacation rentals at your fingertips.
Peak Season Highlights
Spring (March to May)
During spring, the region experiences mild and pleasant weather, making it an ideal time to explore the local surroundings comfortably.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
Fall (September to November)
Autumn offers cooler temperatures and fewer tourists, providing a peaceful atmosphere for your stay in this destination.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Off-Season Highlights
Summer (June to August)
While summer brings warmer weather, it is also the busiest time of year, so early booking can help secure the best vacation rentals here.
Average Temperature Daytime: 85°F to 95°F - Nighttime: 70°F to 75°F
Winter (December to February)
During winter, the area sees cooler and sometimes unpredictable weather, which may be ideal if you prefer quieter times and lower rates for your stay.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Headland
How to Book Your Headland Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Headland
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals 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 outdoor grilling with a private barbecue area to host gatherings during your stay.
- Take advantage of spacious yards or gardens ideal for outdoor play and relaxation.
- Make the most of community pools or swimming areas often available in local rental properties.
- Relish mornings on a screened porch or patio, perfect for enjoying the region’s pleasant climate.
- Experience outdoor sports facilities such as tennis courts, basketball courts, or volleyball areas.
- Benefit from scenic walking trails or nature paths that are accessible directly from your rental.
- Admire picturesque views from decks or balconies that highlight the natural beauty of this destination.
Top Attractions Around Headland
What attractions are nearby?
In this area, you can explore a variety of outdoor activities and local attractions that showcase the natural beauty and charm of Headland, Alabama, providing a memorable experience during your stay.
Family Activities
- Headland Community Park: You can enjoy outdoor activities and family picnics at this welcoming park, perfect for a relaxing day in the region.
- Historic Headland Museum: Explore local history and culture with engaging exhibits that offer educational fun for children and adults alike.
- Lake Headland Recreation Area: Spend time fishing, boating, or simply unwinding by the water at this scenic spot central to family-friendly entertainment in the area.
- Headland Sports Complex: Participate in or watch youth sports games and tournaments, making it a lively place for active families visiting here.
Adult Activities
- Golfing at Headland Golf & Country Club: Enjoy a relaxing day on the course, perfect for improving your swing amidst scenic fairways in this inviting region.
- Exploring Headland Nature Trails: Discover the area's natural beauty by walking or biking along designated trails that showcase the local flora and fauna.
- Visit to Headland Historic Museum: Immerse yourself in the region's history through engaging exhibits and artifacts that tell the story of this charming destination.
- Cruising the Nearby Waterways: Experience serene boat rides or kayaking opportunities on the area's lakes and rivers, offering a tranquil escape for adventure seekers.
Headland Travel Tips
How Can You Make the Most of Your Stay?
- Research Local Attractions: Discover the hidden gems and popular spots in this region to enhance your stay and create memorable experiences.
- Plan for Outdoor Activities: Take advantage of the area's natural beauty by scheduling outdoor pursuits that suit your interests and the local climate.
- Choose a Convenient Location: Select vacation rentals near key amenities or scenic areas to maximize your leisure time and convenience here.
- Check Travel Seasons: Be mindful of the best times to visit, ensuring you enjoy favorable weather and avoid peak crowds in this destination.
Transportation Options
- Headland Municipal Airport: This regional airport offers convenient domestic flights, making it easy for you to arrive and begin your stay in the area.
- Interstate Highway Access: Major highways connect here, providing flexible options for driving to nearby cities and attractions during your visit.
- Local Taxi Services: Reliable taxi companies operate throughout the region, offering quick and straightforward transportation around Headland and its surroundings.
- Public Transit Systems: Bus services in the area provide an affordable way to explore the region without the need for a private vehicle.
Local Customs Options
- Southern Hospitality: Expect warm welcomes and friendly interactions that reflect the region’s famous hospitality when visiting this destination.
- Local Festivals: Participating in community festivals offers a glimpse into the area's rich cultural traditions and local pride.
- Traditional Cuisine: Savor authentic Southern dishes that highlight the region’s culinary heritage and local ingredients.
- Festive Greetings: It's common to exchange cheerful greetings that embody the area's welcoming atmosphere during your stay here.
Headland Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals 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 Vacation Rentals in Headland:
- Claire’s Cottage is located on 7 secluded acres with a coded privacy gate.
- Peaceful 3BR/2BA Hidden Lake Home Near ACOM w/WiFi
- CLOSE TO EVERYTHING! The Hidden Gem Dothan
- Newly remodeled. 5 mi to Dothan shopping. 3 mi to Dothan Airport.
- 3BD Adult Retreat - Fire Pit, Putting Green, Mins to DT
- Cozy, Quiet 3 Bed 2 Bath Home with Private Pool!
- The Cottages 2 2BR2BA Dothan Pet Friendly Gorgeous Pool, Pickle Ball court, Gym
- The Cottages: 2BR/2BA Dothan Pet Friendly Gorgeous Pool, Pickle Ball court, Gym
- Great Dothan location near shopping and airport
- Quiet Family Home in Headland w/Games & Yard
2. How many vacation rentals have private pools in Headland?
There are 3 vacation rentals with private pools near Headland. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Headland are best for families?
If you are looking for a family-friendly vacation home in Headland, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Headland:
4. How many Rentbyowner vacation rentals are available in Headland?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 121 in the Headland area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Headland.
5. What is the cancellation policy for vacation rentals in Headland, Alabama?
Cancellation policies vary depending on the individual property listing. To understand the specific terms, please review the cancellation policy outlined in the listing details or contact the property owner directly before booking.
6. Are there any additional fees I should be aware of when booking a vacation rental in this area?
Additional fees such as cleaning fees, service charges, or local taxes may apply and will be detailed on the listing page. Be sure to read the full fee breakdown before confirming your reservation.
7. How can I verify the safety and reliability of a vacation rental in Headland, Alabama?
You can review guest ratings, reviews, and the host’s response history on the listing to assess reliability. Trusted platforms also provide secure payment options and support to ensure your booking experience is safe and dependable.
8. What amenities are typically included in vacation rentals in this region?
Amenities vary by property but commonly include essentials like Wi-Fi, kitchen facilities, heating or air conditioning, and parking. Details about specific amenities are available within each listing.
9. How do I find the best vacation rental deals in Headland, Alabama?
To secure the best rates, consider flexible travel dates, compare multiple listings, and look for properties offering discounts or special promotions. Reading reviews can also help identify quality accommodations that offer good value.
Headland Top Rated Vacation Rentals
Hotel
9.2(137 Reviews)
1 Bath
Oceanfront- Pool
- Ocean View
- Balcony/Terrace
US $175/Night
7 Nights - US $1,225
US $147/Night
7 Nights - US $1,029
Hotel
9.0(147 Reviews)
2 Baths
204.51 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $139/Night
7 Nights - US $972
Hotel
9.0(146 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $164/Night
7 Nights - US $1,149
US $97/Night
7 Nights - US $681
US $111/Night
7 Nights - US $779
Hotel
8.8(312 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $117/Night
7 Nights - US $819
US $109/Night
7 Nights - US $760
