Islesboro Island Rentals
From $384 per night (USD)VRBO
Beautiful and cozy sanctuary in Islesboro
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Located on the gorgeous and relaxing island of Islesboro, enjoy what this 2-bedroom house has to offer. This delightful ...
From $384 per night (USD)VRBO
From $341 per night (USD)Expedia
~ Peaceful And Quaint Family Cottage On An Island In Maine ~
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This summer cottage on an island in Maine overlooks the beautiful Penobscot Bay. This rustic cottage has a moderate livi ...
From $341 per night (USD)Expedia
From $454 per night (USD)VRBO
Beach-Side Cottage: Windows By The Sea
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 9
Secluded down a dead-end dirt road, our beach-side cottage sits in the lap of a beautiful sand and pebble beach, so clos ...
From $454 per night (USD)VRBO
From $216 per night (USD)Expedia
Island log home in Maine with ocean views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Modern 2 bedroom log home on Islesboro, an island off the coast of Maine with daily ferry access. Secluded lot. One qu ...
From $216 per night (USD)Expedia
From $155 per night (USD)VRBO
Inchcliffe--Islesboro Island Waterfront Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
If you are a small family of two or three looking for a quiet and beautiful place in which to spend a vacation, please ...
From $155 per night (USD)VRBO
From $283 per night (USD)Expedia
Secluded And Rustic Island Cabin On The Bold And Rocky Penobscot Bay Coast...
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This 16' x 24' cabin sits on eleven acres of ocean frontage at 105 feet above sea level (one of the highest points on Is ...
From $283 per night (USD)Expedia
From $386 per night (USD)VRBO
Island Beachside Cottage with Sunset Views
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Perched on Marshall Cove, Summerset Cottage gives you immediate access to Islesboro's best beach. The gentle slope is pe ...
From $386 per night (USD)VRBO
From $864 per night (USD)Expedia
MASSIVE Oceanfront Dark Harbor Home on ISLESBORO
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
This elegant 5+ bedroom Victorian Cottage has been carefully restored and renovated to highlight the natural charm and c ...
From $864 per night (USD)Expedia
From $553 per night (USD)VRBO
Charming Waterfront Cottage Just Steps from East Penobscot Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
2 WEEK MINIMUM RENTAL. Stay in a charming oceanfront cottage on 4 wooded acres just feet from the beach. Enjoy morni ...
From $553 per night (USD)VRBO
From $265 per night (USD)VRBO
Islesboro Island Maine Oceanfront Home on 12 Private Acres
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Dates for May and June 2026 now open. Please note, I am not yet accept bookings for 2027. Beautiful, private oceanfron ...
From $265 per night (USD)VRBO
From $383 per night (USD)VRBO
Take a Ferry to the Island of Your Dreams.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your vacation home - a barn style summer home on Broad Cove near the ferry. Imagine yourself relaxing on the ...
From $383 per night (USD)VRBO
From $162 per night (USD)VRBO
~ Cozy Cabin in the woods On Penobscot Bay Right Near the water ~
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is a 300 square foot, one room, efficiency cabin. That Is Perfect For A Couple's Getaway On An Island In Maine! Se ...
From $162 per night (USD)VRBO
From $644 per night (USD)VRBO
The Anchorage, an oceanfront home with two private beaches on Islesboro Island
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
The Anchorage is a spectacular oceanfront peninsula property on Islesboro's eastern rocky coast overlooking Penobscot Ba ...
From $644 per night (USD)VRBO