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Check prices for these dates

Next weekend
7 Saf. - 9 Saf.
In two weeks
14 Saf. - 16 Saf.
In one month
28 Saf. - 2 Rab. I
In two months
28 Rab. I - 30 Rab. I

Compare 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)
"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
Oceanfront Condo overlooking Rockland Harbor and pier. Permit#STR22-30
Newly renovated living area. Elegant and comfortable. VIEWS!

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
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)
"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
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)
"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
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)
"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
Downtown 2-Bedroom with Shared Harbor-side Patio
Property grounds

Downtown 2-Bedroom with Shared Harbor-side Patio

Downtown 2-Bedroom with Shared Harbor-side Patio
Downtown condo, three bedrooms, water view
Exterior

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
Aerial 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
Deluxe Oceanfront 1 BR at Samoset Resort
Golf

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
Exterior

Island log home in Maine with ocean views

10.0 out of 10, Exceptional, (68)
"Cozy, quiet cabin with a good layout and nice view on the water. Easy check-in and check-out process. Host is very responsive. "
Island log home in Maine with ocean views
Trade Winds on the Bay
Interior

Trade Winds on the Bay

3.5 star property
8.2 out of 10, Very Good, (161)
"Above and beyond service "
The price is SAR 351
SAR 383 total
includes taxes & fees
3 Feb - 4 Feb
Trade Winds on the Bay
Cozy Cabin By The Pond, Sleeps 2
Welcome to the Cozy Cabin

Cozy Cabin By The Pond, Sleeps 2

10.0 out of 10, Exceptional, (162)
"Extremely cozy, easy to find, great hosts, close to some very cute towns."
The price is SAR 450
SAR 744 total
includes taxes & fees
3 Feb - 4 Feb
Cozy Cabin By The Pond, Sleeps 2
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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