
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 12 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.

Entire House/Mill/modern vintage on 35 Acre Pond
The house has a access trail to 35 acre Mason Pond. This newly built home has an abundance of open space with native wood walls and ceilings. The kitchen and living room is on the second floor capturing views of surrounding hills and distant ocean. 2nd fl A/C only .The second floor has sliding glass doors opening to a 36 ft covered deck.The 2 bedrooms are on the 1st floor with queen size beds. Both bedrooms have 10 foot ceilings with their own private French doors access to yard & 6 acre field

Blue Arches: waterfront vacation home on 18+ acres
A lovely custom-designed home nestled in a pristine oceanfront cove, Blue Arches offers 18 acres of privacy and relaxation on beautiful Deer Isle, Maine. Charming Stonington Village is just five minutes away & features harbor-front restaurants, shops, kayaking adventures, galleries and the acclaimed Opera House Arts center. Day trips to nearby Bar Harbor, Mt. Desert Island and Acadia National Park expand your possibilities and let you create a truly memorable vacation for your friends & family.

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

Sunny Waterfront Home Overlooking Blueberry Field
5 acres of lawns, gardens, and meadows and a gentle rocky beach on Blue Hill's Salt Pond, a protected inlet of the Atlantic Ocean. The house faces south towards the water and overlooks a gorgeous blueberry field that turns a majestic shade of deep red in the fall. Please feel free to reach out with us for more information or to inquire about a longer term booking. The house has two bedrooms and baths on the main level and an two additional bedrooms, bathroom, and living space downstairs.

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.

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.

Perched atop the Coast of the Atlantic Ocean
Enjoy sweeping vistas of the Atlantic Ocean from this 2002 home perched among spruce trees above the rocky coast. Watch for bald eagles and seals. Fall asleep to the sound of crashing waves. Walk down to the edge of the ocean to lounge or picnic. Walk 6 minutes or drive the 0.1 miles to the park entrance. Hike the Little River Trail. The house has vaulted ceilings, panoramic views, fully equipped kitchen, and whirlpool bath.

Hot Tub Time Machine
Step into a vibrant world with this collection of paintings that celebrate color and texture. Enjoy pristine beaches and forest and spread out in this 2600 sq ft house with cathedral ceilings, 2 fireplaces, sauna and well stocked kitchen. Explore the island and it's hikes and fine sand beaches or take a dip in the quarry. Discover a dramatic narrative with this striking home that juxtaposes nature and fantastic mythical creatures
Popular amenities for Islesboro house rentals
House rentals with a pool

Luxe Liberty: Getaway with Heated Indoor Pool!

Coastal Retreat with Pool and Cheerful Vibes

House in the woods

Dog Friendly Midcoast Cape

Ocean View Retreat with Heated Pool / Hot Tub

Acadia get away.! With pool and hot tub

3-BR Serene Waterfront Home with In-Ground Pool

1798 - Spacious - Sleeps 10 - On Morgan Bay
Weekly house rentals

The Colby House - Built in 2025!

#1 NE Small Coastal Town- Castine, Shell Cottage

Bayview House 1br 2ba Stunning Harbor Views

Salt Pond Farmhouse

Dockside Oasis

Delight<Farmhouse

Sternman's Cottage

Newer Constructn 4bed coastal retreat near Camden
Private house rentals

River View | Private Hot Tub | Poplar Treehouse

Sweeping Views with Private Beach in Castine

Sun, Salt & Sand at Heart Rock House!

Trinity Cottage, Cozy 2 bedroom, walk to water.

Bucksport oasis, w/hot tub! One hour to Acadia NP!

The Swan Lake House - Lakefront-Private Beach

Red Barn at The Appleton Retreat

The South Bay Maine House "on the rocks"
When is the best time to visit Islesboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $430 NZD | $430 NZD | $430 NZD | $465 NZD | $430 NZD | $577 NZD | $602 NZD | $602 NZD | $594 NZD | $508 NZD | $430 NZD | $430 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 |
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 $172 NZD per night before taxes and fees

Verified guest reviews
Over 1,890 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
30 properties have a dedicated workspace

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

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Islesboro rentals

4.8 Average rating
Islesboro stays are highly rated by guests—averaging 4.8 out of 5!
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- Acadia National Park
- Pemaquid Beach
- Northeast Harbour Golf Club
- Pemaquid Point Lighthouse
- Acadia National Park Pond
- Coastal Maine Botanical Gardens
- Hermon Mountain Ski Area
- Dragonfly Farm & Winery
- Sandy Point Beach
- Sand Beach
- Lighthouse Beach
- Bear Island Beach
- The Camden Snow Bowl
- Eaton Mountain Ski Resort
- Kebo Valley Golf Club
- Wadsworth Cove Beach
- Spragues Beach
- Farnsworth Art Museum
- Rockland Breakwater Light
- Narrow Place Beach
- Islesboro Town Beach
- North Point Beach
- Pebble Beach
- Billys Shore




