Stay If You Dare - Vacation Rentals in Headland
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Luxury Places to Stay in Headland
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Top-Rated Vacation Rentals with a Pool in Headland
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Pet-Friendly Vacation Rentals in Headland
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Large Vacation Homes & Villas in Headland
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Wheelchair Accessible Vacation Homes in Headland
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Headland Vacation Rentals and Airbnb Places to Stay Under $200
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Instantly Bookable Vacation Homes in Headland
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About Headland Vacation Rentals
With more than 121 Headland vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Stayifyoudare and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Headland.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Stayifyoudare Headland, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Headland. Places to stay near Headland are 394.73 ft² on average, with prices averaging US $160 a night.
Stayifyoudare makes it easy and safe to find and compare vacation rentals in Headland with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Headland
| Type | Count |
|---|---|
| Vacation Homes | 57 |
| Hotels | 50 |
| Cottages | 9 |
| Holiday Apartments | 4 |
| Cabin Rentals | 1 |
Use these Quick Filters to Find a Vacation Rental in Headland
★ Pro Tip: Stayifyoudare makes it easy to compare the best listings on Stayifyoudare homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Stayifyoudare homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Headland.
Weather in Headland
View the weather forecast for Headland before booking your Headland Vacation Rentals to confirm your best time to go.
Top Attractions Around Headland, AL
Stayifyoudare offers a large selection of top attractions around Headland. Research things to do on your vacation before you visit Headland.
Headland Vacation Rental Frequently Asked Questions
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
- 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
- Great Dothan location near shopping and airport
- The Cottages: 2BR/2BA Dothan Pet Friendly Gorgeous Pool, Pickle Ball court, Gym
- Hailey's Retreat-6 minutes to Downtown Dothan! Spacious home, sunroom, backyard!
- The Cottages 3 2BR2BA Dothan Pet Friendly Gorgeous Pool, Pickle Ball court, Gym
How many vacation rentals have private pools in Headland?
There are 2 vacation rentals with private pools near Headland. Top-rated homes that have access to a swimming pool include:
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:
How many vacation rentals are available in Headland?
Currently, the total number of properties listed in 2026 is over 121 in the Headland area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Headland.
