Islesboro vacation rentals

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Top-rated vacation rentals in Islesboro

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

Guest favorite

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.

Mar 11 – 18

R2,578 ZAR per night
Guest favorite

Guesthouse in Orland

4.99 out of 5 average rating, 102 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!

Feb 12 – 19

R1,860 ZAR per night
Guest favorite

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.

Jan 10 – 17

R2,493 ZAR per night

Popular amenities for Islesboro vacation rentals

Stay near Islesboro's top sights

Lincolnville Beach42 locals recommend
Whale's Tooth Pub & Restaurant - Lobster Rolls - Cocktails - Craft Beer - Waterfront Dining23 locals recommend
Lobster Pound Restaurant16 locals recommend
McLaughlin's Lobster Shack11 locals recommend
The Hoot26 locals recommend
Dots18 locals recommend

Other great vacation rentals in Islesboro

Guest favorite

Apartment in Rockport

4.96 out of 5 average rating, 349 reviews

ONE BIG ROOM Studio in Rockport

Jan 22 – 29

R2,689 ZAR per night
Guest favorite

Guesthouse in Lincolnville

4.98 out of 5 average rating, 161 reviews

Peaceful Suite - Hiking, Beach, Nature

Oct 29 – Nov 5

R3,004 ZAR per night
Guest favorite

Yurt in Appleton

4.96 out of 5 average rating, 221 reviews

SUMMER ROSE a Yurt for ALL Seasons

Feb 17 – 24

R3,084 ZAR per night
Guest favorite

Apartment in Rockland

4.94 out of 5 average rating, 193 reviews

Sunny New England House Apartment STR22-44

Feb 9 – 16

R2,312 ZAR per night
Guest favorite

Chalet in Lincolnville

4.98 out of 5 average rating, 132 reviews

Charming home near ocean & close to Camden/Belfast

Apr 25 – May 2

R3,761 ZAR per night
Guest favorite

Guesthouse in Lincolnville

4.94 out of 5 average rating, 120 reviews

Ocean View Beach Loft Carriage House Lincolnville

Oct 17 – 24

R2,913 ZAR per night
Guest favorite

Apartment in Belfast

4.89 out of 5 average rating, 207 reviews

Comfy, Convenient Studio Apartment Near Downtown

May 23 – 30

R2,789 ZAR per night
Guest favorite

Apartment in Rockport

4.96 out of 5 average rating, 231 reviews

The perfect getaway - Camden/Rockport/Rockland

Dec 12 – 19

R2,701 ZAR per night
Guest favorite

Guest suite in Rockland

4.96 out of 5 average rating, 157 reviews

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

Aug 22 – 29

R2,820 ZAR per night
Guest favorite

Apartment in Rockport

4.94 out of 5 average rating, 193 reviews

Centrally Located Apartment! Rockport, Maine

Feb 13 – 20

R2,512 ZAR per night
Guest favorite

Cottage in Brooklin

4.98 out of 5 average rating, 178 reviews

Historic School House now with High Speed Internet

May 30 – Jun 6

R2,532 ZAR per night
Guest favorite

Home in Brooks

4.89 out of 5 average rating, 196 reviews

Cedar Swamp Farm

Nov 4 – 11

R2,156 ZAR per night

Other great vacation rentals in Islesboro

Guest favorite

Cottage in Belfast

4.9 out of 5 average rating, 111 reviews

Belfast Ocean Front Cottage

Oct 15 – 22

R3,480 ZAR per night
Guest favorite

Place to stay in Owls Head

4.97 out of 5 average rating, 157 reviews

A comforting sweet off grid cabin near the beach!

Nov 11 – 18

R2,716 ZAR per night
Guest favorite

Home in Camden

5.0 out of 5 average rating, 151 reviews

Quaint 3 Bedroom In Town Camden Home

Feb 14 – 21

R2,650 ZAR per night
Superhost

Cottage in Islesboro

4.83 out of 5 average rating, 42 reviews

Ocean Front Island Cottage

Feb 22 – Mar 1

R3,455 ZAR per night
Guest favorite

Guesthouse in Islesboro

4.97 out of 5 average rating, 30 reviews

Main Cabin at Coveside on Islesboro

Jun 17 – 24

R8,471 ZAR per night
Guest favorite

Cottage in Islesboro

5.0 out of 5 average rating, 20 reviews

"The Dory" on Penobscot Bay, Mid-Coast Maine

Oct 10 – 17

R6,490 ZAR per night
Guest favorite

Tiny home in Islesboro

4.95 out of 5 average rating, 19 reviews

"Bohemian Bungalow" Studio Island Guest Cottage

Nov 18 – 25

R3,223 ZAR per night
Superhost

Condo in Northport

5.0 out of 5 average rating, 3 reviews

Lovely 1 bedroom apartment in Northport

Feb 21 – 28

R2,199 ZAR per night
Guest favorite

Cottage in Northport

4.86 out of 5 average rating, 43 reviews

Mellow Yellow - cozy Penobscot views in Bayside!

Oct 1 – 8

R2,472 ZAR per night
Superhost

Home in Northport

5.0 out of 5 average rating, 5 reviews

Bear Pond Cottage - Waterfront in Maine!

Jun 11 – 18

R12,308 ZAR per night
Guest favorite

Home in Northport

4.97 out of 5 average rating, 34 reviews

Cliff House - Ocean Views! Architectural designed.

Nov 21 – 28

R11,975 ZAR per night
Guest favorite

Home in Lincolnville

5.0 out of 5 average rating, 32 reviews

Antique Barn Apartment at Salt Water Farm

Nov 4 – 11

R6,845 ZAR per night

Quick stats about vacation rentals in Islesboro

Total rentals

150 properties

Rentals with dedicated workspaces

70 properties have a dedicated workspace

Pet-friendly rentals

50 properties allow pets

Family-friendly rentals

90 properties are a good fit for families

Total number of reviews

5.5K reviews

Nightly prices starting at

R947 ZAR before taxes and fees

Frequently Asked Questions

  • Do house rentals in Islesboro have a bbq area?

    Absolutely! We offer over 40 house rentals with a bbq area in Islesboro. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Islesboro?

    Islesboro has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Islesboro have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Islesboro. Enjoy a tailored experience with all the comforts you desire.

  • Do cabin rentals in Islesboro have wireless internet?

    Absolutely! We offer over 10 cabin rentals with wireless internet in Islesboro. Enjoy a tailored experience with all the comforts you desire.

  • Are there cottage rentals with a dedicated workspace in Islesboro?

    Yes! Work meets play with ease at over 10 cottage rentals in Islesboro featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly cottage rentals in Islesboro?

    Four-legged friends are welcome in Islesboro. Choose from more than 10 cottage rentals for guests traveling with pets.

  • How much does it cost to stay in apartment rentals in Islesboro?

    Experience the best of Islesboro with our apartment rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • What are the most popular amenities for Cottage Rentals in Islesboro?

    Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with a bbq area, over 10 homes with air conditioning, over 30 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Waldo County
  5. Islesboro