logo ×

Property Management

Your Island Connection Property Management

Give Us A Call At:

(207) 833-7779

Your Island Connection Property Management

Give Us A Call At:

(207) 833-7779

Free Rental Evaluation

Discover Your Property’s True Potential

  • This field is for validation purposes and should be left unchanged.

100% Safe & Secure

Why Hire A Property Manager When I Can Do It Myself

Most people that rent their homes themselves use HomeAway and/or Airbnb to advertise their properties. We recognize that these are great listing sites, but they cannot “take care” of your home. Besides checking the house multiple times during the process of check-ins and check-outs we are also always monitoring the homes during the tenant’s stays.

Your Island Connection, LLC was founded in 1982, and we remain locally owned and operated. Heather Allen purchased the business in 2011 after working four years with the company founder. Since the purchase, we have more than doubled the number of our reservations and continue to increase by at least 10% each year. We also have 50% of tenants that return year to year and another 10% who return every couple of years. In fact, each year since 2016 rentals have increased 15%. Our knowledgeable crew of friendly, hardworking area natives has over 50 years of combined service in the hospitality industry. We are proud of our fishing community and enjoy sharing its hidden treasures with our owners and renters alike. We take great pride in providing excellent, and timely service to both our owners and renters.

We are constantly continuing to educate ourselves about the industry. We attend local, regional, and national meetings/conferences which keep us up to date on market trends, legislation, and new technology. Heather is the previous President of the VRPOME (Vacation Rental Professionals of Maine) which is an association of Professional Rental Managers from around the Maine that focus on current Legislative issues. This group has been successful in making sure regulations at the state level (specifically Maine) will not put the vacation rental industry out of business, this would have impacted both companies and individuals rent properties.


What makes a home a good YIC vacation rental?


Our rental area is Harpswell, Bailey Island, Orr’s Island, Great Island, and Cundy’s Harbor.


We have a list of items that we require each home to have to ensure the guests have everything they need while at your home. For example, a lobster pot, enough utensils & dishes, and a grill are a few items on the list.

Safety 1st

It is state law that we require smoke detectors, carbon monoxide detectors, and a fire extinguisher. Handrails, no exposed wires, and other various safety hazards also need to be addressed.


We want to help you generate the highest income we can for your property. In order to do that we need the most availability you can give us, ideally, that means letting us rent 6 out of 8 of the biggest peak weeks (July & August).

Proximity to the Water

Waterfront and/or Waterview properties are ideal rentals. However, we will consider properties that have nearby water access.

Furniture & Beds

We strongly encourage that furniture and beds be in good shape, clean, and comfortable. Nothing is worn out and unable to keep its shape.


You must provide proof that your property has proper insurance for functioning as a rental.

Our Marketing

Where Do We Advertise?

Our Website

Our Website: We have a professional reservation management system that keeps our calendars synced in real-time, provides an individual listing for each property, marketing tools, online booking, an owner portal, and other great features to aid in our productivity. The reservation management system stays up to date on what best brings our website to the forefront on google. In addition, we accept ALL major credit cards and checks through our reservation management system. We make our marketing decisions based on our knowledge of the current rental market, and utilize Google Analytics to track our web-based advertising. We also attend local, regional, and national meetings/conferences to ensure we are well educated and informed of any new market trends, and any legislation that may impact our area.


We have an optional tier to advertise here. The calendar ties in with our website to ensure updated calendars.


A listing on this site is included automatically. The calendar ties in with our website to ensure updated calendars.

Bowdoin College

We utilize the fact that many visitors come in to visit with their children or return to a special place after going to college here. We advertise both our company and individual rentals in different variances through Bowdoin College.

Maine Tourism Association

There are a variety of opportunities and publishing that this association puts out that Your Island Connection advertises in addition to their website.

Harpswell Business Association

We have a listing on their website in addition to being in their “map” which is a printed publication that is distributed for free to area businesses for their patrons to pick up for free.

At different times we advertise in the following places depending on the property.

  • Trips with Pets
  • Flipkey
  • Other Magazines and Newspapers across the country
  • Local Hospitals and businesses that have traveling employees, which includes contacting their human resources department to give them information.
  • Local Publications including but not limited to Harpswell Anchor, and Downeast Magazine


What are the benefits of using Your Island Connection as my vacation rental agency?

24/7 Customer Service! We make ourselves available 24/7 to you and your guests. We check email constantly, even outside of our business hours. We also carry a cell phone for after-hours emergencies to ensure if something has happened, i.e.; water leak, lockout, etc. it can be handled immediately.

Hire Vendors

Which includes but is not limited to trash collectors, cleaners, window washers, carpet and upholstery cleaners, lawn care, contractors, plumbers, electricians, and appliance repair. We have great relationships with local vendors and because of that we can get quicker than normal response time from them and in most cases, receive discounts should they be billed through us.

Follow up on vendor work

We are happy to check the work being done at your house and make sure it is done up to your standards. Should you want any pictures of the work we are also happy to send them to you.

Replace or repair items that may be needed in the house

We will make the extra trip to town to be sure the coffee pot that had broken is replaced ASAP or the ripped screen is repaired in a timely manner.

Small minor repairs or problems

We assess every issue that may happen at your vacation home before calling any vendors to fix or troubleshoot. If we can fix it ourselves, we will! We do not like spending unnecessary money and feel you shouldn’t have to either!

Preventative Maintenance

Every time we go to your property, we are constantly checking to make sure there are no leaks, no insect activity, etc. If we find any issues, we will take preventative measures to make sure those problems do not get larger.

Featured Properties

Worried about your house sitting empty for the season? Great news, we offer caretaking services!

Your Island Connection, LLC has been caretaking properties for nearly 30 years. It is not necessary for you to have your house listed as a rental for us to provide these services. We offer property checks as a year-round, seasonal, or periodical basis. Year-round and seasonal checks are done on a weekly basis, and the basics consist of exterior checks, interior walk through, and checking for leaks or break-ins. There are many more things we check at various properties, so we take things case by case and make a caretaking checklist to suit each property and its owner’s needs. We are on call 24/7 and respond to alarm calls, as well as being available to open the property for any service people.

Please click HERE for more information!

Owner Testimonials

I have been utilizing the services of Your Island Connection since purchasing my home on Orr's Island in August of 2016. The owner and her team are polite, professional and extremely knowledgeable about the vacation rental industry. They have also been great to accept new ideas from me, who has been in the hospitality industry for 30+ years. As an owner who lives two plus hours from my vacation rental, they have been extremely helpful in emergency situations and also for general maintenance that my husband and I cannot do ourselves. Their communication is impeccable. I would recommend Your Island Connection highly from both the home owner perspective and also the renter perspective!

Robin Z. | Property Owner

We own several vacation properties in different parts of the world and have each of them managed by a local management company. In this comparative group, Your Island Connection stands out as the premium service provider that we do business with. The reasons are simple; attention to detail, taking care of the customers' needs, and going beyond expectations! I highly recommend YIC to both owners and renters for a professional yet still personal experience!

John C. | Property Owner

We have recently given both of our rental houses in Harpswell to Your Island Connection for rental management. I was impressed with the services that they provide from the moment I received the contract. Their contract and promotional materials were thorough, very clear and professional.
I am very pleased with the marketing of the houses - I have seen our house in banner ads on Airbnb and I think this contributes to the very high occupancy rate we have seen for our house.
The team at YIC could not be more helpful or professional. I truly appreciate that they call me if there is ever a problem - they are easy to reach and respond promptly to emails, texts and phone calls. They offer tips about improving the rentals - what tenants would like, etc. which enhances the houses and their appeal to tenants.
Heather, Michaela and Hillary are an absolute pleasure to work with and are experts on the area and have excellent connections to resources which is also incredibly helpful when anything goes wrong and also helpful to tenants who need any help or advice.

Heather B. | Property Owner

I don’t know what we’d do without them! In every respect we give Heather, Michaela and Hillary the highest marks for the terrific and very professional work they have done for many years renting our two properties. Their follow-through on all issues is excellent and appreciated, but particularly when it comes to solving problems they can be counted on to come up quickly with the helpful answer we were looking for. They are everything we could hope for in a rental agent: professional, knowledgeable, and courteous.

Bob S. | Property Owner

We live across the country from our Bailey Island property and rent it out through YIC when we are not in town. We have complete peace of mind that the property is being maintained and watched after by the YIC team. They handle everything from sourcing and vetting tenants, to insuring things go smoothly during their stay, to preparing the house for the next tenants arriving... even if those next tenants are us. They also let us know what’s needed whether toilet paper or repairing a leaky roof, or what's wanted, like a reading light for a tenant that likes to curl up with a book. Even then they don’t just point out a problem- they help with the solution whether it’s recommending a handyman or greeting a delivery at the house.

Aaron S. | Property Owner

I have been very happy working with Your Island Connection. Not only were they helpful when I switched from another company to them, they have been able to find renters who have respected our property in much the same way we do. Coming back after the renters leave and finding our place clean, neat and well cared for is one the best services Your Island Connection provides.

David E. | Property Owner

I'm Interested!

How do I get started?

1. Please click HERE to fill out your information so we can contact you to begin the process!
2. We will send you a contract to sign along with an owner information sheet.
3. Get Rental Insurance.
4. Go through our rental ready checklist to get your home prepared for pictures and guests.
5. We will arrange to have our professional photographer take pictures, and we will also do a Matterport 3-D tour for our website.
6. Schedule your regular maintenance items over the winter to ensure they get done in early spring – septic pumping, window cleaning, carpet cleaning, chimney sweeps, furnace tune-ups, and tune-ups for any appliances that uses propane. These items need regular testing and cleaning to keep them running safely and efficiently. Periodic water testing is also necessary, but should be done early spring before the rental season begins.
7. Make sure your house number is visible from the road for 911 emergency purposes.

Thank you for considering Your Island Connection, LLC as your Vacation Rental Professionals, we look forward to working with you. If you have any questions, please don’t hesitate to contact us!

~ The Crew @ YIC ~