
House holiday rentals in Islesboro
Find and book unique houses on Airbnb
Quick stats about house rentals in Islesboro

Total holiday rentals
Explore 120 holiday rentals in Islesboro

Nightly prices starting at
Islesboro holiday rentals start at $208 NZD per night before taxes and fees

Verified guest reviews
Over 2,050 verified reviews to help you choose

Family-friendly holiday rentals
100 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 70 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
110 of Islesboro holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Islesboro rentals

4.8 Average rating
Islesboro stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated house rentals in Islesboro
Guests agree: These houses are highly rated for location, cleanliness and more.

Cute Midcoast Cottage w Hot Tub
Kick back and relax in this ideally located modern cottage. Enjoy a soak in the hot tub or the peace of the covered porch. Situated in the heart of midcoast Maine, this cottage has it all. An elegant kitchen that awaits your culinary delights, a spacious living area, a primary bedroom with a TV, a kingsize bed and a luxurious bath with a soaking tub and a walk-in rainfall shower, plus twin bunk beds for the kiddos. A small store and a farm to table restaurant are conveniently across the street.

Cozy Cottage on the Penobscot – Panoramic Luxury!
Escape to your private waterfront retreat where tranquility meets luxury. Our Coastal Maine Cottage style home rests on a granite ledge that disappears twice daily with the tide. Enjoy a sun-filled interior with cherry floors, a gourmet kitchen, and a private deck for sunrise coffee or evening wine. Wake to sweeping Penobscot River views & unwind by the fire pit at river’s edge. Just 10 minutes to downtown Bangor, with easy access to urban amenities, Bar Harbor, and Acadia Park. @cozycottageinme

Moss House: A Modern Waterfront Cabin in the Woods
Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

"The Roost" Cottage
"The Roost" is a bright 1400 sqft. 2 bedroom c.1890 cottage that has been recently renovated and painted located on a two acre property with a coffee roaster Green Tree Coffee and Tea as well as another very small cabin called "The Lair". We are located 400 yards from Lincolnville Beach, 2 miles from Mt. Battie State park, 4 miles from downtown Camden, and 12 miles from Belfast. We are a very dog friendly property, plenty of room for your dog to roam out back in small pasture. Sorry no cats

Downtown-Walk to All Things Rockland
Cute, convenient, and clean recently renovated 1930’s cottage has two bedrooms, sleeps 4, a private backyard, and is within walking distance to downtown, restaurants, nightlife, co-op & supermarket, museums, shops, art galleries, Harbor Park, ferry and the waterfront. Enjoy off-street parking and an ocean view with the sun glistening off the harbor at the end of the street. This is a perfect home-base for a coastal Maine vacation and festivals. Discounts offered for weekly and monthly stays!

[Trending Now]Belfast City Park Ocean House
Welcome to an exquisite retreat nestled on a tranquil dead-end lane in the thriving coastal City of Belfast. With private access to Belfast City Park and Ocean, this charming space offers unparalleled serenity, boasting breathtaking views of Penobscot Bay and beyond. The meticulously manicured grounds offer an ideal setting for relaxation and outdoor entertaining, with the added allure of explorations along the shoreline or tennis/pickleball courts at park/year round hot tub. No parties.

Historic Stephenson Farm on 35 acre Mason Pond
This water front historic Stephenson Farmhouse is a cozy 3 bedroom farmhouse that sits on 5 acres with frontage on Lower Mason Pond. A bird lovers paradise along with sightings of beaver & river otters. Trail from house leads to waterfront, canoes, paddles & PFD’s and a picnic table. We’ve maintained the antiquity of the house along with many antique pieces of furniture. Enjoy amazing sunsets, expand your birding life list, pick apples and blueberries in season. . . on a nature preserve.

Bayview House 1br 2ba Stunning Harbor Views
Do you crave balmy summer evenings or frosty winter days that make you feel like you've been transported back to a simpler time? Or long for days spent on the water or experiencing village life with friendly locals in charming pubs tasting local eats? Experience the simple joys of life with rustic yet modern amenities offered at this coastal 2-story home. Whether daily strolls by the water or taking in the sunset on your deck, you'll fall in love with this lovely New England destination.

Newly renovated cottage in the heart of Downeast
The Woodlands is tucked away on a quiet street off Route 1, minutes from downtown Ellsworth. Newly renovated in 2021, this delightful one bedroom, 2 bathroom cottage has new appliances, including a gas range and washer and dryer, along with all the thoughtful amenities you'll need for a relaxing retreat. With central access to Acadia National Park and all your coastal adventures, the Woodlands is a perfect destination for a peaceful getaway in the heart of Downeast Maine.

Secluded Retreat w/ Luxe Hot Tub & Forest Views
Tucked near the woods of Maine, this peaceful cabin offers the perfect escape. Soak in the private hot tub under the stars, curl up by the electric woodstove, or work remotely with fast Wi-Fi and forest views. The cabin features a comfy king bed, full kitchen, clean modern bath, and self check-in. Enjoy your morning coffee in the sunroom or take a short drive to explore Belfast and the coast. Quiet, cozy, and surrounded by nature—ideal for rest, romance, or reflection.

Hot Tub Art Sail Loft. Swans Island
Experience the beauty of nature in this art lovers abode. The dynamic brushstrokes and colors create an atmosphere of tranquility, making it an ideal retreat for those seeking inspiration and a connection with nature. Just steps to fisherman’s cooperative with daily catch lobsters. Walk to the lighthouse or lay back in the hot tub after you drink your coffee in the widows walk with harbor views. Please read other details, we are on an island.

Sweet home away (pet friendly)
Single floor living at its finest. Conveniently located to both Camden and Rockland, enjoy this 3 bdrm 1.5 bath home in a great country setting. Just 1/2 mile to route 1 and very close to the ocean. Come enjoy the large back deck over looking the peaceful maine woods. The front door in about 50’ from the road, which can be busy at certain time of the day. There is 1 ring doorbell for everyone’s security outside the front door of the house.
Popular amenities for Islesboro house rentals
House rentals with a pool

Cozy, fun, 3 bedroom home with a pool and Hot Tub.

The Jarvis Homestead | Historic Maine Mansion

New Boho Cape with Pool! Fenced yard, pet friendly

Coastal Retreat with Pool and Cheerful Vibes

House in the woods

Peaceful 4 Bedroom Maine Retreat with Private Pool

Dog Friendly Midcoast Cape

Ocean View Retreat with Heated Pool / Hot Tub
Weekly house rentals

Sweeping Views with Private Beach in Castine

#1 NE Small Coastal Town- Castine, Shell Cottage

Antique Barn Apartment at Salt Water Farm

Hilltop Retreat

Double On The Rocks, ocean view family retreat

A quiet place on the coast of Maine

Casa on the Bagaduce River

Above & Beyond
Private house rentals

NEW luxury WATERFRONT home! ADA,roof deck, garage+

Eleanor's Cottage

Belfast Beach House

Harbor Haven

Extreme Sunrise - Oceanfront Cottage

*NEW* Bagaduce River Cottage @ Old Hart Farm

The Swan Lake House - Lakefront-Private Beach

Red Barn at The Appleton Retreat
When is the best time to visit Islesboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $434 NZD | $607 NZD | $434 NZD | $468 NZD | $434 NZD | $581 NZD | $607 NZD | $607 NZD | $599 NZD | $585 NZD | $512 NZD | $390 NZD |
| Avg. temp | -7°C | -6°C | -1°C | 6°C | 13°C | 18°C | 21°C | 20°C | 16°C | 9°C | 3°C | -3°C |
Destinations to explore
- Rentals with a fireplace Islesboro
- Rentals with beach access Islesboro
- Beachfront rentals Islesboro
- Waterfront rentals Islesboro
- Rentals with a washing machine and dryer Islesboro
- Rentals with a patio Islesboro
- Cabin rentals Islesboro
- Family-friendly rentals Islesboro
- Pet-friendly rentals Islesboro
- Apartment rentals Islesboro
- Rentals with breakfast Islesboro
- Cottage rentals Islesboro
- Rentals with outdoor seating Islesboro
- Rentals with a fire pit Islesboro
- Fitness-friendly rentals Islesboro
- House rentals Waldo County
- House rentals Maine
- House rentals United States
- Acadia National Park
- Acadia National Park Pond
- Pemaquid Beach
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- Schoodic Peninsula
- The Camden Snow Bowl
- University of Maine
- Sand Beach
- Rockland Breakwater Light
- Farnsworth Art Museum
- Camden Hills State Park
- Cellardoor Winery
- Maine Lighthouse Museum
- Moose Point State Park
- Bass Harbor Head Light Station
- Hollywood Slots Hotel & Raceway
- Echo Lake Beach





