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Search Condo Rentals in Islesboro

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Compare 10 Condo Rentals in Islesboro with updated reviews, rates, and availability.

Charming dog-friendly condo with kitchenette, balcony, fast WiFi, & W/D

6.0 out of 10, (1)
"The property accommodated the needs for my wife, dog and I with close walking proximity to town. "
Charming dog-friendly condo with kitchenette, balcony, fast WiFi, & W/D

Downtown Getaway w/ Full Kitchen & Furnished Porch - Walk to the Beach/Harbor

8.8 out of 10, Excellent, (3)
"Great location in Castine! Very easy to get to nearby towns. Property needs blinds on the windows (windows facing the driveway/parking, bathroom, and bedroom). Felt very exposed with half-curtains on ground level. Other than that, property was perfect!"
Downtown Getaway w/ Full Kitchen & Furnished Porch - Walk to the Beach/Harbor

Comfy Downtown Getaway w/ Full Kitchen - Close to the Beach

8.8 out of 10, Excellent, (13)
"The beds were a joke and the spaces were dirty (mouse poop and birdseed on top of the refrigerator). The living room furniture is worn and uncomfortable. I would not recommend this property."
Comfy Downtown Getaway w/ Full Kitchen - Close to the Beach

Comfortable Getaway for Two w/ Kitchenette - Right in the Heart of Downtown

10.0 out of 10, Exceptional, (2)
"This rental was in great condition and very clean! Everything was exactly as pictured and listed and we had a wonderful time in Castine and exploring the area nearby."
Comfortable Getaway for Two w/ Kitchenette - Right in the Heart of Downtown

Oceanfront Condo overlooking Rockland Harbor and pier. Permit#STR22-30

10.0 out of 10, Exceptional, (4)
"Great location. Nice condo. Great for the family needs."
Oceanfront Condo overlooking Rockland Harbor and pier. Permit#STR22-30

Downtown 2-Bedroom with Shared Harbor-side Patio

Downtown 2-Bedroom with Shared Harbor-side Patio

Deluxe Oceanfront 1 BR at Samoset Resort

Deluxe Oceanfront 1 BR at Samoset Resort

Downtown condo, three bedrooms, water view

Downtown condo, three bedrooms, water view

Samoset Resort on The Ocean 1 Bedroom Condo Golf Tennis Pickleball Pool Dining

Samoset Resort on The Ocean 1 Bedroom Condo Golf Tennis Pickleball Pool Dining
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Islesboro

Island log home in Maine with ocean views

10.0 out of 10, Exceptional, (66)
"A nice quiet spot tucked off the beaten path. All you need - coffee galore, a comfy bed and the space to relax. "
Island log home in Maine with ocean views

~ Peaceful And Quaint Family Cottage On An Island In Maine ~

9.8 out of 10, Exceptional, (44)
"We just finished a five-night stay at this property. Rustic is the perfect way to describe it along with offering modern amenities like 1 and 1/2 baths, a complete kitchen, washer dryer and great internet. It's a great secluded location with the General Store just a five minute drive away."
~ Peaceful And Quaint Family Cottage On An Island In Maine ~

Trade Winds on the Bay

3.5 star property
8.2 out of 10, Very Good, (147)
"We got in very late. They had a lock box for us to get our keys after hours (texted us the code) and then checked on us the next day to make sure we made it safely. "
The price is SAR 394
SAR 468 total
includes taxes & fees
5 Jan - 6 January 2025
Trade Winds on the Bay
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

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