All Properties

Click here is view ALL of our vacation properties.

By Location

Bailey Island, Orrs Island, Great Island, Cundys Harbor, Harpswell Neck 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!

SPECIALS

Are you looking for a deal? Here you will find any properties that are having discounts or specials.

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

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. 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 Highview - Weekly Rental Only Homeport Cottage - Weekly Rental Only Shackteau - $800/month plus utilities Stormhaven - $1600/month plus utilities Tree Tops House - $1500/month plus utilities (Plowing, cable and internet included) West Shore House - $1300/month plus utilities