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

Total holiday rentals
Explore 70 holiday rentals in Islesboro

Nightly prices starting at
Islesboro holiday rentals start at $112 AUD per night before taxes and fees

Verified guest reviews
Over 2,020 verified reviews to help you choose

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

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 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.

Lakefront Log Cabin on Pleasant Lake
Best view on the Lake! 500' of frontage out on a point. Private boat launch and dock site available. Covered deck to watch the sunset. Outdoor firepit, as well as indoor gas insert. Propane grill on site. Plenty of parking available. In the winter, ideal location for snowmobiling and ice-fishing. Right on to the lake and then 4 locations to get on local/ITS trails. Great fishing 200’ from the porch. Once the ice is out, hit the black crappie and Smallies from the convenience of a private launch

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

Brand new Scandinavian cottage: dock & kayaks!
Brand new architectural cottage and detached 'boathouse' with sweeping elevated ocean views both east and west, private waterfront lawns and deep water dock with kayaks. This property was built in 2020 so expect a fresh and clean experience on one of Harpswell's most private peninsulas. Watch the sunrise from the cantilevered 2nd floor deck, sit by the campfire on your private lawn oceanside, or walk down to the dock for a paddle in the west facing protected cove. The best of coastal Maine!

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.

[Trending Now]Belfast Ocean Breeze
Welcome to an exquisite retreat nestled on a tranquil dead-end lane in the thriving coastal town of Belfast. With private access to Belfast City Park and Ocean, this charming space offers unparalleled serenity, and boasting breathtaking views of Penobscot Bay and beyond. The exceptional grounds offer an ideal setting for relaxation with the added allure of explorations along the shoreline or tennis/ pickleball at park/ year round hot tub. Near downtown and Rt. 1. No parties.

Private Lakefront Cottage Close to Bar Harbor
Newly renovated historic lakefront home on 8 acres with a lot of privacy. Conveniently located only 20 minutes from airport, this 2-story cedarshake home sits on the water's edge and is close to Bar Harbor and surrounding picturesque towns for shopping, restaurants and sightseeing. Large wrap-around porch (with dining table that seats 10 and several comfy seating areas) for family fun & outdoor dining. Large deck, perfect for swimming, lake fun and canoe rides. AC in bedrooms.

Seaside House/Upstairs
Enjoy everything coastal Maine has to offer with this as your home base. The views are outstanding and the house is well appointed and well maintained. This house encompasses the second and third floors, with great ocean views. The first floor is a separate apartment. The property has a large back yard to relax or play in and a dedicated BBQ. The house sits across the street from Clam Cove and is not directly on the beach. Beach access is private, quick and easy.

Sea Breeze Cottage in idyllic Castine Maine!
Sea Breeze Cottage, Castine, Maine Experience quintessential New England charm in this cozy Castine cottage. Freshly and tastefully renovated and only a short stroll from beautiful Fort Madison beach. Recharge your batteries and relax to the sound of the nearby bellbuoy! Discover all coastal Maine has to offer from the comfort of Sea Breeze Cottage!
Popular amenities for Islesboro house rentals
House rentals with a pool

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

New Boho Cape with Pool! Fenced yard, pet friendly

Coastal Retreat with Pool and Cheerful Vibes

House in the woods

Three Sisters Retreat

Bar Harbor, near Acadia with seasonal dock & pool

Dog Friendly Midcoast Cape

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

Duck Cove Get Away

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

Stonington Dream House

Fun Lakefront Cabin near Acadia

Summer Oceanfront Retreat- Acadia/Bar Harbor

The South Bay Maine House "on the rocks"

Cottage on the sea

Blue Heron
Private house rentals

Lupine Landing

Salt Pond Farmhouse

The Cottage at Red Top - Cozy Lakeside Year-Round

The Bunkhouse at Salisbury Camp

Red Barn at The Appleton Retreat

Salty Trails Maine Cottage

Light-filled House amid Beauty, ideal for dogs

Alewife House
When is the best time to visit Islesboro?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $349 AUD | $349 AUD | $349 AUD | $377 AUD | $349 AUD | $468 AUD | $489 AUD | $489 AUD | $482 AUD | $471 AUD | $412 AUD | $314 AUD |
| 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
- Boston Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Island of Montreal Holiday rentals
- Capital District, New York Holiday rentals
- Quebec City Area Holiday rentals
- Halifax Holiday rentals
- Laval Holiday rentals
- Québec Holiday rentals
- Portland Holiday rentals
- Newport Holiday rentals
- Martha's Vineyard Holiday rentals
- Rentals with a patio Islesboro
- Rentals with outdoor seating Islesboro
- Pet-friendly rentals Islesboro
- Cottage rentals Islesboro
- Fitness-friendly rentals Islesboro
- Rentals with beach access Islesboro
- Apartment rentals Islesboro
- Rentals with breakfast Islesboro
- Rentals with a fireplace Islesboro
- Rentals with a washing machine and dryer Islesboro
- Cabin rentals Islesboro
- Family-friendly rentals Islesboro
- Rentals with a fire pit Islesboro
- Beachfront rentals Islesboro
- Waterfront 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
- The Camden Snow Bowl
- Sand Beach
- Farnsworth Art Museum
- Rockland Breakwater Light
- University of Maine
- Schoodic Peninsula
- Bass Harbor Head Light Station
- Moose Point State Park
- Maine Lighthouse Museum
- Cellardoor Winery
- Hollywood Slots Hotel & Raceway
- Camden Hills State Park




