All Properties

Click here is view ALL of our vacation properties.

By Location

Bailey Island, Orrs Island, Great Island, Cundys Harbor, Harpswell Neck, Brunswick, West Bath and Phippsburg

Saturday to Saturday Rentals

These houses rent from Saturday to Saturday in the peak season. There is generally some flexibility on days in the off season.

Friday to Friday Rentals

These houses rent from Friday to Friday in the peak season. There is generally some flexibility on days in the off season.

NEW properties for 2019

We have a few new additions to our rental inventory!


Book at least 4 nights at any of the following properties and get 1 night 50% off! Use the code 4THNIGHT50 * *Offer valid on reservations for stays between September 7, 2019 - October 26, 2019. Cannot be combined with other offers. Cannot be applied to already placed reservations. Only valid on the properties shown on this "specials" page.

4 NIGHT minimum properties

Cant come for a week? No worries, we now offer shorter stays even during peak season!

2 NIGHT Minimum Properties

We are excited that we now offer a few properties with a 2 night minimum during peak season!

1 Bedroom

Your Island Connection - 1 Bedroom Vacation Rentals

2 Bedroom

Your Island Connection - 2 Bedroom Vacation Rentals

3 Bedrooms

Your Island Connection - 3 Bedroom Vacation Rentals

4+ Bedrooms

Your Island Connection - 4+ Bedroom Vacation Rentals

Pet Friendly

These properties are all dog friendly, please know that there are some breeds that certain places dont allow due to insurance. Generally only one dog would be allowed per property but certain places have made exceptions, so please feel free to reach out to us and ask.

Sunrise Views

These properties offer sunrise views from the house.

Sunset Views

These properties offer sunset views from the house.

Kayak Friendly

Kayak friendly - you can launch your kayak from this property or the nearby right away

Swim Friendly

Swim Friendly - you can access the water from a rocky/pebbly beach and/or dock

Winter Rentals

Please see below for rates for our winter rentals. Please inquire about minimum rental period. Berkshire - $950/month plus utilities Cundys Harbor Hideaway - $2500 per month plus utilities Fairhaven Farm - $1150/month plus utilities (plowing included; shoveling not included) Giffin Log Cabin - Weekly Rental Only Gulls Rest - Weekly Rental Only Harbors Edge - $1000/month plus utilities Highview - Weekly Rental Only Homeport Cottage - Weekly Rental Only Parciak House - Weekly rental only Safe Haven - Weekly rental only Shackteau - $800/month plus utilities Sunset Shore House - Weekly Rental Only The Studio - $900/month plus utilities Tree Tops House - $1500/month plus utilities (Plowing included) -- Home can have two bedrooms closed off and offered as 3 bedroom - $1200/month plus utilities Watsons Landing - $1200/month plus utilities West Shore House - $1300/month plus utilities Whitesails Cottage - $700/month plus utilities