1. Jamaica
  2. Hanover
  3. Montego Bay
  4. Headland
  5. Rentals by Owner

Headland Rentals by Owner

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10.0 (2 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Why Choose Rent By Owner for your Headland vacation rental?

What makes our Rentals by Owner special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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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 Rentals by Owner stay?

Choosing the optimal time to visit here can enhance your experience by aligning your stay with the region’s most favorable weather and local events, ensuring a memorable and enjoyable vacation in this beautiful Jamaican destination.

Peak Season Highlights

spring
December to April

During this period, you can enjoy the region's warm, sunny weather, ideal for relaxing on the beaches of Headland and the surrounding areas. It is a popular time for visitors seeking a tropical escape.

Average Temperature Daytime: 28-30°C - Nighttime: 20-22°C
spring
July to August

The summer months attract travelers looking to experience the vibrant local culture and outdoor activities while enjoying the consistent warm climate. This is the busiest season for booking rental accommodations in the area.

Average Temperature Daytime: 30-32°C - Nighttime: 22-24°C

Off-Season Highlights

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May to June

This shoulder season offers a quieter atmosphere with fewer tourists, making it a great time to explore the region’s natural beauty while enjoying more affordable rental options.

Average Temperature Daytime: 29-31°C - Nighttime: 21-23°C
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September to November

During these months, the area's weather begins to cool slightly, and you might experience less crowding, ideal for those seeking a peaceful retreat in the region. It's also a good time for deals on vacation rentals by owner.

Average Temperature Daytime: 27-29°C - Nighttime: 19-21°C

Weekly Weather Forecast for Headland

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.

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 private outdoor swimming pool to cool off in the warm Caribbean sun.
  • Relax in a spacious patio or veranda perfect for outdoor dining and lounging.
  • Make the most of lush gardens or landscaped yards that surround your rental.
  • Take advantage of outdoor grilling facilities for barbecues with friends or family.
  • Benefit from secure parking areas ideal for exploring the local area by car.
  • Experience scenic views from balconies or terraces overlooking the region’s natural beauty.
  • Utilize outdoor recreation spaces such as tennis courts or volleyball courts, if available.
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Family Activities

  • Relax at Lucea Bay Beach: Enjoy a calm day on the golden sands, perfect for families seeking a peaceful beach experience in the area.
  • Visit the Hanover Museum and Heritage Center: Discover local history and culture through engaging exhibits that captivate both kids and adults.
  • Explore the lush gardens of the nearby Green Grotto Caves: Take an adventurous tour through underground caves surrounded by tropical scenery, offering fun for the entire family.
  • Experience local cuisine at family-friendly restaurants in the region: Savor authentic Jamaican flavors with menus suitable for children, making mealtime memorable here.
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Adult Activities

  • Relax on the local beaches: You can unwind by enjoying the pristine sands and clear waters that define this destination’s coastline.
  • Explore heritage sites and historical landmarks: Discover the rich history of the region through its well-preserved sites and cultural landmarks.
  • Experience vibrant local cuisine: Savor authentic Jamaican dishes at nearby eateries, offering a taste of the area's culinary traditions.
  • Engage in water-based adventures: Take part in activities such as snorkeling or diving to explore the colorful marine life surrounding this locale.

Headland Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Events: Research upcoming cultural festivals and events in the region to enrich your stay with authentic experiences unique to here.
  • Choose a Prime Location: Opt for a rental close to the beaches or popular neighborhoods to maximize your leisure time and enjoy the best of this destination.
  • Engage with Your Host: Communicate openly with your owner to get personalized tips on local dining, hidden gems, and must-visit spots within the area.
  • Pack Smart and Light: Bring versatile clothing suitable for the tropical climate and outdoor activities, ensuring comfort throughout your visit to the region.

Transportation Options

  • Private Car Transfers: You can arrange for private car transfers, offering a comfortable and flexible way to explore the area around Headland and Lucea.
  • Taxis and Ride-Sharing Services: Taxis and ride-sharing options are readily available for convenient travel throughout the region, ensuring you reach your destination with ease.
  • Public Buses: Local buses provide an economical transportation choice, connecting you to key spots within Hanover and nearby attractions.
  • Rental Cars: Renting a vehicle allows you to independently discover the scenic landscapes and hidden gems across this part of Jamaica at your own pace.

Local Customs Options

  • Respect for Local Spiritual Practices: You’ll find that honoring traditional religious customs is important here, especially during community celebrations and ceremonies.
  • Emphasis on Greeting Etiquette: A warm handshake or friendly greeting often accompanies interactions, reflecting the region’s welcoming spirit.
  • Celebration of Cultural Festivals: Participating in local festivals provides insight into the area's rich history and vibrant heritage.
  • Adherence to Traditional Dress Codes: Visitors are encouraged to dress modestly and respectfully when visiting religious sites or attending community events.

Headland Rentals by Owner Frequently Asked Questions

1. What are the top vacation rentals in Headland?

2. How many Rentbyowner vacation rentals are available in Headland?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 155 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. 

3. What is the cancellation policy for a rental by owner in Headland, Lucea?

Cancellation policies vary between listings. You should review the specific policy on the rental's page or contact the owner directly to understand the terms and any potential fees.

4. How do I confirm my reservation at a rental property in Hanover?

Once you complete your booking through Rent By Owner, you'll receive a confirmation email with details. For additional verification or special requests, reach out to the property owner directly.

5. Are there any additional fees when booking a rental by owner here?

Additional fees such as cleaning or service charges may apply and are detailed in the listing. Be sure to read all the fee information carefully before completing your reservation.

6. What amenities can I expect at rentals in this region?

Amenities vary by property but often include essentials like Wi-Fi, air conditioning, and kitchen facilities. Check the specific listing for a comprehensive list of amenities available at your chosen rental.

7. How do I inquire about special requirements or accommodations?

You can contact the owner directly through the Rent By Owner platform to discuss any special needs or requests before finalizing your booking.

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10.0 (2 Reviews)
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  • TV