This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
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Islesboro Vacation Rentals Show this location only Back to top
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Take a Ferry to the Island of Your Dreams.
3BR+/1.5BA
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Sleeps 6-8
– Islesboro #412090
$600/wkd, 1500 pw, 5250 pm
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Charming Waterfront Cottage Just Steps from East Penobscot Bay
3BR/2BA
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Sleeps 6
– Islesboro #354953
$1000 TO $1500/WK
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Crow's Nest: 100 Year Old, Charming, Restored, Island Cottage
2BR+/1BA
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Sleeps 4-5
– Islesboro #82587
$ 750 - $ 900/Week
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Islesboro Island Maine Oceanfront Home on 12 Private Acres
4BR+/2.5BA
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Sleeps 8
– Islesboro #356787
From $1,250/wk to $2,500/wk
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Waterfront on Coombs Cove, East Islesboro
3BR/2.5BA
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Sleeps 6
– Islesboro #347845
From $950 to $1800/wk
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Beachfront Family Cottage, Glorious Views of Penobscot Bay
3BR+/1.75BA
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Sleeps 4
– Islesboro #178424
$1600/wk
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Fabulous Island House
7BR/5BA
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Sleeps 14
– Islesboro #301343
$4000- $5000/wk
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Maine Island Home on Marshall Cove Road
3BR/1BA
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Sleeps 4-6
– Islesboro #413501
900 - 1000/WK
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Spectacular Waterfront Property with Private Beach
3BR+/2BA
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Sleeps 5
– Islesboro #305170
$2000- $2800/wk
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Waterfront Cottage, Gorgeous Views of Penobscot Bay
3BR+/1BA
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Sleeps 4-6
– Islesboro #217331
$1200/wk
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Relax at Heavenly Daze - Steps to a Picturesque Typical Maine Beach
3BR/2.5BA
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Sleeps 7
– Islesboro #3528780ha
$1986 per week 7 night min stay
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The Ultimate in Peace and Quiet on Penobscot Bay
3BR/2.5BA
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Sleeps 6-8
– Islesboro #445915
$2730 per week 7 night min stay
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Ocean Front Home, Private Beach, Woods and Trails to Hike
3BR+/1BA
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Sleeps 9
– Islesboro #297489
$1200- $1500/wk
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The Red House Farm
2BR+/1BA
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Sleeps 4-6
– Islesboro #323365
$850- $1250/wk
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Maine Island Beachfront Cottage-Great Views-Pebbly/Sandy Beach-Island Charm
3BR/1BA
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Sleeps 8
– Islesboro #115996ha
$193 - $336 per night
- Surrounded by Water . . . a Very Special Place . . . 7/14-20 Reduced to $1700 3BR+/1.5BA – Sleeps 10 – Islesboro #112614ha
- Waterfront Victorian Island Farm 4BR/4BA – Sleeps 12 – Islesboro #115834ha
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Private Waterfront Home on Huge Estate Grounds
3BR+/2.5BA
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Sleeps 9
– Islesboro #147060ha
$243 - $428 per night
- Charming 4BR Farmhouse, Spectacular Views Across Penobscot Bay, Private Beach 4BR/2BA – Sleeps 7 – Islesboro #247971ha
- Oceanfront Cottage, Spectacular Views, 440' Waterfront, Private, Cozy Escape 4BR/1.5BA – Sleeps 8 – Islesboro #158754ha
- Cottage and Boathouse on the Shore. 1BR+/1BA – Sleeps 6 – Islesboro #377499ha
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Take a Ferry to the Island of Your Dreams.
3BR+/1.5BA
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Sleeps 6-8
– Islesboro #412090
Overview of Islesboro Vacation Rentals
With Islesboro Vacation Rentals, You'll Live like a Star
Home to Hollywood celebrities and charming locals, Islesboro, Maine is a quaint town nestled on an island roughly three miles to the east of the mainland. Any vacationer is sure to love the classic New England architecture and the lighthouses that dot the coast. Islesboro vacation rentals are a perfect way to enjoy the small-town feeling while getting away from the hustle-and-bustle of everyday life.
Relax and Rejuvenate in Maine
As one of the most classic tourist destinations in New England, Islesboro lodging is in great demand. Cozy cottages with their warm hearths and ocean views welcome you for a weekend of relaxation. Take a stroll on the sandy beach just outside your vacation rental. Put together your own clam or lobster bake or even take part in a community festival. Islesboro lodging gives you the opportunity to feel almost like you are part of the community as you stroll among the locals and dine in family-owned restaurants and browse for antiques on Main Street.
Mid Coast Islands Cottages
Whether it's for a week or a month, you'll feel swept away as you relax in one of our Mid coast islands cottages. Live like the locals and put your feet up while you watch the sun set over the channel. You've never experienced New England until you've stayed in Islesboro lodging and truly felt what it's like to live on a beautiful coastal island. You won't get the same feel from staying in a chain hotel, and you're sure to miss the amenities you'll get from an Islesboro vacation rental, like a full kitchen. Mid Coast Islands cottages allow you to get away from it all and experience New England the way it was meant to be experienced: in comfort and style.