Photo by Colleen Johnson

Islesboro Holiday Rentals

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Holiday Rentals in Islesboro

Fridge, microwave, oven, stovetop
Island log home in Maine with ocean views
10.0 out of 10, Exceptional, (54)
"My wife and I thought the property was fantastic. It was well maintained and very clean. If you want a nice quiet getaway I would highly recommend this place."
Island log home in Maine with ocean views
Panoramic Suite, 1 King Bed with Sofa bed, Balcony, Harbour View
Trade Winds on the Bay
3.0 star property
7.6 out of 10, Good, (41)
"This property is centrally located in Rockland and within walking distance to the harbor, dining, coffee, shopping, and more. We had a great harbor view from our room. And while Trade Winds is old and needs work (smells old and we had to air out our room every time we came back to it.), it's in the ideal location and we would definitely stay there again; just wish the price was a little less expensive. Customer service and communication was top notch and exceeded all expectations. "
The price is NZ$258
per night
29 May - 30 May
Trade Winds on the Bay
Property grounds
Cozy Cabin By The Pond, Sleeps 2
10.0 out of 10, Exceptional, (129)
"Beatiful property, clean and quiet accommodations. A few peaceful days exploring the greater Belfast area is just what we needed."
The price is NZ$347
per night
28 May - 29 May
Cozy Cabin By The Pond, Sleeps 2
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Oven, stovetop, coffee/tea maker, electric kettle
Cozy Cabin on Blue Hill Farm
9.8 out of 10, Exceptional, (23)
"We enjoyed our stay very much. If it had been warm enough to enjoy all of our meals outside that would have been wonderful. We didn’t plan or pack for any rain but when it poured for a solid day, we were thankful for the cabin’s shelter and wifi and umbrella when we went out. Although we brought an infant and a 2.5yo, I wouldn’t necessarily recommend this property for such little/young kids unless you’re prepared for spotting them up and down the ladder. We loved the hanging indoor swing and our...
Cozy Cabin on Blue Hill Farm
Beach
Oceanfront,Unobstructed Ocean Views, Onsite ocean access to a small sandy beach
10.0 out of 10, Exceptional, (89)
"Maine is spectacular in mid-October. The Primrose Apartment was the perfect location to see the colorful leaves, visit lighthouses and enjoy all both Rockland and Camden have to offer. Alex and Siobhan were gracious, thoughtful and kind hosts. The view of Glen Cove from both the kitchen window and the deck is stunning. The Primrose was the perfect property and location for our stay."
Oceanfront,Unobstructed Ocean Views, Onsite ocean access to a small sandy beach
Exterior
Waterfront cottage with deep water dock, ocean front.
9.8 out of 10, Exceptional, (67)
"The location was new for us. But oh so beautiful and interactive. The host was the best I have encountered in decades of travel. The accommodations were clean and very comfortable. I am ready to book for next spring."
Waterfront cottage with deep water dock, ocean front.
On the beach, sun-loungers
Oceanfront, Onsite Ocean Access to a small beach. Fantastic Ocean & Island Views
9.8 out of 10, Exceptional, (88)
"We renewed our wedding vows at Children’s Chapel. The area is beautiful, beach is amazing, there is a rock on the beach that has dates and names carved all over it from the 1800’s. The host was GREAT Alex told us stories and let us hear his “Alabama accent” LOL. I could’ve talked to him all day. We had a great trip and plan on coming back."
Oceanfront, Onsite Ocean Access to a small beach. Fantastic Ocean & Island Views
Exterior
Private cabin on the Maine coast
9.0 out of 10, Wonderful, (2)
"Great stay!"
The price is NZ$449
per night
29 May - 30 May
Private cabin on the Maine coast
Fridge, microwave, stovetop, coffee/tea maker
Cozy Cottage on Cat Cove w/ Wraparound Deck!
7.4 out of 10, Good, (8)
"Super cute cabin RIGHT on the lake. Wish it would have been warmer during our stay. The cabin is very secluded and quiet with a fire pit outside for relaxing. Be sure to have the directions ready from the property manager as your GPS won't pick the address up."
Cozy Cottage on Cat Cove w/ Wraparound Deck!
Interior
Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range
9.8 out of 10, Exceptional, (6)
"Had the good old field of what we always called a "camp." Kitchen was well stocked with utensils and glassware, etc. The lobster processing facility made for a bit of noise and a pretty steady stream of traffic. A lot of trucks, from pickups to semis coming in and out. Didn't really bother us a whole lot but it might bother other people. Overall the view of the water was pretty nice except for the power lines and there's not much that can be done about that. Have to have electricity after all."
Lovely home with harbor views, gas grill, streaming, W/D, & gourmet range
Property grounds
Secluded house just minutes away from Deer Isle/Stonington villages and beaches!
10.0 out of 10, Exceptional, (27)
"The house was beautiful and exactly what we needed. Mike and Rachael were fantastic."
Secluded house just minutes away from Deer Isle/Stonington villages and beaches!
Property grounds
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town
9.2 out of 10, Wonderful, (60)
"This house was awesome for our family to gather for my daughter's wedding. The wedding party got ready in the beautiful living room and there was plenty of room. Walkable to town and the wedding venue made this spot ideal. Seamless check in and check out."
The price is NZ$1,526
per night
16 Jun - 17 Jun
Perfect location ! Harbor Breeze is on Camden Harbor & walking distance to town
Fridge, microwave, oven, stovetop
Cabin with deck, grill & fire table on 10 private acres - near Crescent Beach
8.0 out of 10, Very good, (4)
"All of the smoke detectors need the batteries replaced. I bought batteries and replaced most of them but there was one still incessantly beeping. The house was great. We will book it again The"
Cabin with deck, grill & fire table on 10 private acres - near Crescent Beach
Property grounds
Stay at the Beach! - Private Balcony - Sunrise
9.8 out of 10, Exceptional, (55)
"We thoroughly enjoyed our stay here. It's very comfortable, has laundry facility and the host was in communicate when we called. We'll be back to stay here in the future!"
Stay at the Beach! - Private Balcony - Sunrise
View from property
Jaw-Dropping Coastal Mountain & Ocean View Post & Beam Log Getaway
9.8 out of 10, Exceptional, (59)
"This home was even better than the pictures! The space is so cozy and decorated beautifully. The hosts left a huge bouquet of fresh flowers for us along with bread, chocolates, and jams. Checking in and out was super easy and the home had all the accommodations you could need. Definitely will be back!"
Jaw-Dropping Coastal Mountain & Ocean View Post & Beam Log Getaway
Beach towels
Owls Head Village Post Office
10.0 out of 10, Exceptional, (130)
"Magical for us and our 10yo, who started asking to come back about 2 minutes after arriving."
Owls Head Village Post Office
Property grounds
Oceanfront retreat with sunrise views, screened porch, & deck
9.8 out of 10, Exceptional, (16)
"We visited the first week in November. The property is gorgeous, but the listings between VRBO and Vacasa (a third party that handles the actual communication for check in and such) have huge discrepancies about being dog friendly. This caused significant stress when we arrived as we had to find the original listing saying we could bring our small dog. I would definitely recommend the property, but just be sure you keep track of what you are agreeing to. Also, the bedrooms were warm enough...
Oceanfront retreat with sunrise views, screened porch, & deck
Property grounds
Close Call - A Charming Oceanfront Cottage
6.6 out of 10, (7)
"Wonderful retreat. I enjoyed watching the tide, the birds, and the walk through the adjacent preserve."
Close Call - A Charming Oceanfront Cottage
Beach nearby
Overview Cottage, Toddy Pond!
8.8 out of 10, Excellent, (34)
"Beatiful view and peaceful"
Overview Cottage, Toddy Pond!
Property grounds
Oceanfront, Unobstructed Views, Onsite Access to the water & small sandy beach.
10.0 out of 10, Exceptional, (104)
"Lovely property and the hosts could not be more accommodating. Very helpful and friendly. The view is amazing."
Oceanfront, Unobstructed Views, Onsite Access to the water & small sandy beach.
Don't see what you're looking for?
See all available properties in Islesboro
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.

Other types of properties in Islesboro you may be interested in

Fridge, microwave, oven, stovetop
Island log home in Maine with ocean views
10.0 out of 10, Exceptional, (54)
"My wife and I thought the property was fantastic. It was well maintained and very clean. If you want a nice quiet getaway I would highly recommend this place."
Island log home in Maine with ocean views
Exterior
The Country Inn at Camden Rockport
2.5 star property
9.4 out of 10, Exceptional, (1003)
"Great location close to Camden, yet quieter and nice grounds"
The price is NZ$248
per night
30 May - 31 May
The Country Inn at Camden Rockport
Private beach, fishing
Colonial Gables Oceanfront Village
2.5 star property
9.4 out of 10, Exceptional, (1005)
"Very nice. Quiet "
The price is NZ$214
per night
30 May - 31 May
Colonial Gables Oceanfront Village
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Islesboro holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Islesboro. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Islesboro. Seeing all the best attractions is bound to make you fall in love with Islesboro. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Islesboro short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Islesboro?

Yes, there are holiday rentals close to the most popular sights in Islesboro, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Islesboro has to offer?

Island log home in Maine with ocean views: This highly rated holiday home rental in Islesboro offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a garden.

How many holiday rentals are there in Islesboro?

With 11 Expedia holiday rentals, you're guaranteed to find just the right place for your Islesboro stay.

What’s there to see and do in Islesboro?

While exploring the area, visit family-friendly sights like Penobscot Marine Museum, or get outside and enjoy nature at Warren Island State Park. Lincolnville Beach and Pitcher Pond are a couple of places you'll find in the wider area.

What’s a holiday rental in Islesboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Islesboro. Holiday rentals offer extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for families.

Recent reviews of Islesboro properties
Expedia verified reviews