We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Airbnb your place

Vacation rentals in Islesboro Island

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Islesboro Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

1 of 3 pages

Apartment in Searsport

4.82 out of 5 average rating, 292 reviews

Lakefront Vacation Apartment in Searsport ME

All season private top floor apartment. Hammock, loungers, floats. Acadia/State parks close. Canoe, kayaks, hot tub/wood floating dock (seasonal use), fire pit, grill, swim, fish. Modern/Antique furnished: queen bed plus loveseat twin. Massage/lounger. 2nd queen, twin inflatables. Fully equipped kitchen. Families w/kids, business guests welcome. Wifi smart TV. Great hikes, mountain bike rentals close. Snow shoes/sled included, skiing close. Separate entrance/apt above home not full home.

Feb 6 – 13

G$19,492 GYD per night

Yurt in Appleton

4.96 out of 5 average rating, 225 reviews

SUMMER ROSE a Yurt for ALL Seasons

SUMMER ROSE - Overlooking the Field of Dreams pasture, and future pond, is a spacious wooden yurt with a spectacular ceiling, personal hot tub and "Hideout" a screened in sanctuary. The Appleton Retreat is situated on 120 acres of privately owned land. To the south, a short walk from Summer Rose, is the Pettengill Stream, a resource protected area where you can view wildlife or kayak; and to the north, a wooded trail leads to a secluded pond on 1,300 acres of Nature Conservancy protected land.

Nov 24 – Dec 1

G$33,986 GYD per night

Guesthouse in Lincolnville

4.97 out of 5 average rating, 327 reviews

"The Lair" Guesthouse

"The Lair" is a just recently renovated small 200 square foot cabin with vaulted ceilings and plenty of natural sunlight. The building is located close to Green Tree Coffee and Tea, a coffee roaster, so the aroma of coffee will be in the air. We located about 400 yards South of the Islesboro Ferry and Lincolnville Beach and 2.4 milres North of Camden Hills State Park and Mount Battie. Free coffee and tea everyday, all day! We are closed for Winter, will re-open Mid-April. Thank you.

May 16 – 23

G$28,434 GYD per night

Guesthouse in Lincolnville

4.98 out of 5 average rating, 161 reviews

Peaceful Suite - Hiking, Beach, Nature

Welcome to the “East Wing”! The complete apartment is new: salt box style with beautiful views of nature (hummingbirds, fireflies, starry skies). The East Wing is first to greet the sun in the morning. Enjoy your coffee on the private deck, or sip wine at night by the fire pit. Close to Tanglewood Rd (4H camp) , Camden Hills State Park trails, and Lincolnville Beach(1 -2 miles). The area is quiet- yet just a few miles away from shopping and restaurants in Camden, Belfast, & Rockland.

Oct 6 – 13

G$32,896 GYD per night

Guesthouse in Orland

4.99 out of 5 average rating, 103 reviews

Cozy cottage in Orland Village-Penobscot Bay area

Charming cottage in Orland Village, 2 minutes from Bucksport, a short walk away from the Orland River and its estuary on the Penobscot Bay. Nestled on 3.5 acres of wooded land, 300 ft behind an 18th-century colonial house. Completely self-contained with equipped kitchen. Fast 400 Mbs cable internet/WiFi. 45 minutes to Acadia National Park, 30 min. to Belfast, 20 min. to Castine. Perfect base for hiking, kayaking, sailing, or discovering the maritime past of the area. Pet friendly!

Jan 17 – 24

G$20,515 GYD per night

Apartment in Belfast

4.99 out of 5 average rating, 261 reviews

Room with a Brew

Welcome to our new building. "A Room With a Brew" is located above Belfast's newest craft brewery, Frosty Bottom Brewing. A small community supported brewery open 2 days/week for 3-4 hours for beer share members. Guests can request a tour of the brewery and sample some fresh beer. Owners live in downtown Belfast and are available should any issues arise during your stay. The apartment/brewery is located 3 miles from downtown on a quiet road that offers local hiking and biking.

Dec 8 – 15

G$27,071 GYD per night

Home in Appleton

4.96 out of 5 average rating, 122 reviews

The Barn

I call my place "The Barn" because as I was finishing it it took the shape and feel of a barn. It's not a barn. It's a quiet post and beam open concept building (a Jamaica Cottages kit) set among the fields of Appleton Maine. You'll sleep in the loft or on a futon on the main floor. The bathroom is huge, 10X10, with a heated floor. It's an open concept kitchen and living space. From Appleton you are 20 miles away from the tourist destinations of Camden, Rockland, and Belfast.

May 21 – 28

G$29,726 GYD per night

Guesthouse in Sedgwick

4.96 out of 5 average rating, 235 reviews

Tiny house with AC!!

A tiny guest house (450 sq ft) overlooking the Benjamin River. AC!!. Enjoy a cup of coffee on your private porch. Living area has a smart tv (no cable, but internet available to access your streaming account). DVD's also available. Kitchenette comes with Keurig with k-cups included, mini fridge, coffee maker/filters, toaster oven, microwave, 2 burner hot plate (no oven), dishes/pots and pans. There is a loft with an army cot. Not suitable for children under age 5.

Feb 28 – Mar 7

G$29,132 GYD per night

Cabin in Freedom

4.9 out of 5 average rating, 288 reviews

Cozy Lakefront Cabin in Freedom, ME

Our secluded, very quiet and private two bedroom cabin with loft features a bug-free screened-in porch on its large deck. The cabin overlooks peaceul Sandy Pond, inhabited by bald eagles, loons, and herons. Watch beautiful sunrises and sunsets, and swim, fish and kayak from our dock. We're close to coastal Belfast, Unity, MOFGA (annual Common Ground Fair), Waterville, Acadia and Camden. Eat at The Lost Kitchen, visit the Amish, hike the Hills to Sea Trail.

Dec 14 – 21

G$17,153 GYD per night

Cottage in Rockport

4.95 out of 5 average rating, 165 reviews

Designer’s Coastal Retreat with Simple Luxuries

A designer’s stunning retreat just a short walk to Rockport harbor. This newly renovated 1920’s one bedroom cottage is tucked into a forested granite hillside with oversized windows to take in the view. Artfully furnished with a minimalist sensibility, the space has been fully winterized in order to be a year round sanctuary. A top of the line steam shower, heated bathroom floor, modern gas fire place, and pigmented plaster walls add touches of luxury.

Mar 24 – 31

G$30,289 GYD per night

Guest suite in Rockland

4.96 out of 5 average rating, 157 reviews

Salty Dog Hilltop Guest Suite (permit #SDR22-18)

This guest suite is located in the lower level of our NetZero post & beam home which sits on a mountain overlooking the Penobscot Bay. The over 600 sq. ft. large open floor plan is spacious & clean with a large private patio. The location is quiet and peaceful while only 5 minutes from the action in downtown Rockland and only 15 minutes from Camden. This is a great home base to explore all that the Midcoast area has to offer.

Feb 3 – 10

G$31,166 GYD per night

Place to stay in Owls Head

4.98 out of 5 average rating, 160 reviews

A comforting sweet off grid cabin near the beach!

Get away from it all when you stay at our sweet little off grid cabin in the woods. A place where sleep and peace meet! Surrounded by 15 acres of woods and fields and within walking distance to Birch Point State Park, you'll have a perfect little getaway - all while being only a few minutes away from Rockland.

Nov 6 – 13

G$29,894 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Islesboro Island vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Islesboro Island

Cabin in Deer Isle

4.89 out of 5 average rating, 129 reviews

Long Cove Artist Cottage

May 12 – 19

G$23,302 GYD per night

Apartment in Rockland

4.93 out of 5 average rating, 195 reviews

Sunny New England House Apartment STR24-42

Oct 24 – 31

G$25,023 GYD per night

Apartment in Searsmont

4.97 out of 5 average rating, 109 reviews

Searsmont Studio

Jun 9 – 16

G$22,082 GYD per night

Apartment in Rockport

4.96 out of 5 average rating, 352 reviews

ONE BIG ROOM Studio in Rockport

Mar 4 – 11

G$29,528 GYD per night

Tiny home in Blue Hill

4.94 out of 5 average rating, 155 reviews

New enchanting retreat near Acadia National

Sep 5 – 12

G$29,607 GYD per night

Guest suite in Rockland

4.98 out of 5 average rating, 347 reviews

5 Laurel Studio private entrance STR20-69

Oct 5 – 12

G$20,529 GYD per night

Cottage in Sedgwick

4.99 out of 5 average rating, 188 reviews

Exquisitely Modern Maine Cottage @Diagonair

Apr 30 – May 7

G$99,668 GYD per night

Home in Brooks

4.89 out of 5 average rating, 198 reviews

Cedar Swamp Farm

May 11 – 18

G$23,779 GYD per night

Destinations to explore