
House holiday rentals in Islesboro
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Top-rated house rentals in Islesboro
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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

Treetop Vista: stunning views, modern farmhouse
Relax in this beautiful, architect-designed new house. Enjoy expansive 180-degree views to the south and west, including spectacular sunsets and incredible foliage. Immerse yourself in the scenery, go hiking out the door, go swimming in nearby Hobbs pond, or take a 10-minute drive into Camden to enjoy food, art, shopping, and the ocean. This area is a mecca for outdoor and cultural activities. The house has 3 bedrooms, 2.5 bathrooms, a great room with kitchen, dining, living areas, and a deck.

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

Peaceful Oasis by the Great Salt Bay - 3BR/2Ba
Waterfront Retreat with Gorgeous Views Stunning 3-bedroom, 2-bath home perfect for multi-generational gatherings. Features an open-concept layout, chef’s kitchen, 1st-floor bedroom and bath, 2nd floor with 2 bedrooms and 1 bath. Kayak from your backyard, hike nearby trails, or swim in Damariscotta Lake just a 5-minute walk away. Stay connected with high-speed fiber optic WiFi. Close to charming Newcastle and Damariscotta shops and restaurants. A true oasis for nature and relaxation lovers!

Lavender by the Sea
The Cottage rests over the end of Penobscot River as it opens into the Bay. The Cottage will comfortably accommodate two. The Cottage has a spacious bedroom, full kitchen, dining area, den and an all season porch with rockers. From Cottage there are views of the water and the lavender gardens. The gardens are terraced with a path down to the sea. The Carriage House Suite is available for an additional fee. it has has two bedrooms, a full bath and a sitting area. It can easily sleep four.

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.

The Maine Getaway - Lakefront with Beach
If you are looking for a place to get away and relax, our house on Molasses Pond may be a good fit for you/your family. It is a hidden gem down a dirt road away from hustle and bustle. Peace and quiet is what you’ll find, along with a gorgeous view. It’s a great place for swimming, kayaking, paddle boarding, grilling, fishing, and laying on the hammock. We try to provide you with all the necessities you may need and are happy to answer any questions. We hope you enjoy it as much as we do!

[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.

Hallowell Hilltop Home with Hot Tub & Sauna
Discover this newly renovated 2-bedroom, 1-bathroom home in a quiet family-friendly neighborhood in Hallowell. This home's rustic-modern design, natural light, and all-new amenities make it a perfect getaway. Relax in the hot tub, grill on the deck, enjoy the backyard or visit downtown Hallowell and explore its restaurants, cafes, live music and antique shops. This home is also minutes away from several hiking and walking trails that can all be found in our guidebook.

Cozy home near the coastal town of Camden, Maine!
This home is in a country setting on Hatchet Mountain in Hope near the beautiful Maine coast and about 8 miles from Camden. About a mile from our home, is Hobbs Pond (2 miles long!) with public access for swimming, boating and kayaking. Hiking trails surround us, too! Beaver Lodge, a favorite spot for weddings and other family events, is also nearby. This listing has an exemption for all animals. For safety reasons, it may not be suitable for young children.
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

Luxe Liberty: Getaway with Heated Indoor Pool!

House in the woods

Three Sisters Retreat

Bar Harbor shorefront near Acadia with dock & pool

Dog Friendly Midcoast Cape
Weekly house rentals

Duck Cove Get Away

Ocean Edge, Taunton Bay, near Acadia & Bar Harbor

Sweeping Views with Private Beach in Castine

Extreme Oceanfront House

Downeast Hideaway - Near Ocean & Acadia Ntnl Park

#1 NE Small Coastal Town- Castine, Shell Cottage

Maine Coastal Retreat

*NEW* Bagaduce River Cottage @ Old Hart Farm
Private house rentals

Stonington Dream House

Spacious waterfront home - 2026 Now Booking

Oceanfront home in Castine

"Maine Squeeze" A beachcombers Dream

Red Barn at The Appleton Retreat

Salty Trails Maine Cottage

Spring Discounts! Ocean Front - Mountain View

Cozy Coastal New England Farmhouse
When is the best time to visit Islesboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $365 AUD | $365 AUD | $365 AUD | $395 AUD | $365 AUD | $490 AUD | $511 AUD | $511 AUD | $504 AUD | $492 AUD | $431 AUD | $329 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 |
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 $88Â 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!
Destinations to explore
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- Rentals with beach access Islesboro
- Rentals with a patio Islesboro
- Apartment rentals Islesboro
- Pet-friendly rentals Islesboro
- Cottage rentals Islesboro
- Rentals with a fire pit Islesboro
- Rentals with a washing machine and dryer Islesboro
- Waterfront rentals Islesboro
- Fitness-friendly rentals Islesboro
- Rentals with breakfast Islesboro
- Beachfront rentals Islesboro
- Rentals with a fireplace Islesboro
- Cabin rentals Islesboro
- Family-friendly rentals Islesboro
- Rentals with outdoor seating 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
- Maine Discovery Museum
- Bass Harbor Head Light Station
- Schoodic Peninsula
- Moose Point State Park
- Hollywood Slots Hotel & Raceway
- Maine Lighthouse Museum
- Cellardoor Winery
- Camden Hills State Park




