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Compare 8 Condo Rentals in Islesboro with updated reviews, rates, and availability.

Charming dog-friendly condo with kitchenette, balcony, fast WiFi, & W/D
Charming dog-friendly condo with kitchenette, balcony, fast WiFi, & W/D
6.0 out of 10, (1)

Downtown Getaway w/ Full Kitchen & Furnished Porch - Walk to the Beach/Harbor
Downtown Getaway w/ Full Kitchen & Furnished Porch - Walk to the Beach/Harbor
8.8 out of 10, Excellent, (3)

Oceanfront Condo overlooking Rockland Harbor and pier. Permit#STR22-30
Oceanfront Condo overlooking Rockland Harbor and pier. Permit#STR22-30
10.0 out of 10, Exceptional, (4)

Comfy Downtown Getaway w/ Full Kitchen - Close to the Beach
Comfy Downtown Getaway w/ Full Kitchen - Close to the Beach
8.8 out of 10, Excellent, (13)

Downtown 2-Bedroom with Shared Harbor-side Patio
Downtown 2-Bedroom with Shared Harbor-side Patio

Comfortable Getaway for Two w/ Kitchenette - Right in the Heart of Downtown
Comfortable Getaway for Two w/ Kitchenette - Right in the Heart of Downtown
10.0 out of 10, Exceptional, (2)

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

Deluxe Oceanfront 1 BR at Samoset Resort
Deluxe Oceanfront 1 BR at Samoset Resort
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
Island log home in Maine with ocean views
10.0 out of 10, Exceptional, (69)

Trade Winds on the Bay
Trade Winds on the Bay
8.2 out of 10, Very Good, (203)
The price is SAR 480
SAR 570 total
includes taxes & fees
21 Apr - 22 Apr

Cozy Cabin By The Pond, Sleeps 2
Cozy Cabin By The Pond, Sleeps 2
10.0 out of 10, Exceptional, (167)
The price is SAR 450
SAR 745 total
includes taxes & fees
14 Apr - 15 Apr
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.
Recent reviews of Islesboro hotels
Recent reviews of Islesboro hotels

Trade Winds on the Bay
5/5 Excellent
"A wonderful pool area with great amenities. I don't understand why there are no napkins/paper towels in the rooms. We had to use towels and they were extra dirty after. Our housekeeper for the 4th floor. She was very sweet and kind. Also, she seemed efficient. We enjoyed our stay. Thank you "
A verified traveler stayed at Trade Winds on the Bay
Posted 3 days ago
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