
Waterfront holiday rentals in Islesboro
Find and book unique waterfront accommodation on Airbnb
Top-rated waterfront accommodation in Islesboro
Guests agree: These waterfront accommodation options are highly rated for location, cleanliness and more.

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

Quiet cottage on the bay
Settle in at this mid-coast Maine treasure, where you will find more than you hoped for in a getaway. Located in a private neighborhood and setback on a private road on 2.5 acres. You can take a short stroll down a wooded path to the Belfast bay and watch the sunset or simply enjoy the view from living room. The rocky beach gives you access to a wonderful piece of the Maine coastline. Come make some memories at this unique, pet and family-friendly quiet cottage just 1 mile to downtown Belfast.

Lobstermen's ocean-front cottage
Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

[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.

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.

Cottage by the sea private oceanfront shoreline
Breathtaking oceanfront private cottage. Spiral staircase to second floor bedroom. Sliding glass doors open to wrap-around deck and lawn that slopes to Ocean. 300 + feet of deep water frontage. Separated from lawn by broad rock ledge. Perfect spot for sunbathing or having a campfire in the evening. Enjoy your morning coffee watching lobster and sailboats in the Mussel Ridge Channel. Unbelievable and peaceful views out to ocean and north to the Camden Hills. Unparalleled views everywhere.

Cozy log cabin on private pond, near Reid St Park!
Winter or summer, the Little River Retreat will help you step away from the world - but still be minutes from Reid State Park, Five Islands Lobster, the Georgetown General Store, and the rugged beauty of Midcoast Maine. This is our family camp, with our own books, games, and “vibe”. It is not a hotel, and some things may not be “industry standard”. We love the unique charm of this space and place, and many repeat guests do too. We hope you will treasure (and care for it) as we do!

Tiny house with AC!!
A tiny guest house (450 sq ft) overlooking the Benjamin River. AC!!. Enjoy a cup of coffee on your private porch. Living area has a smart tv (no cable, but internet available to access your streaming account). DVD's also available. Kitchenette comes with Keurig with k-cups included, mini fridge, coffee maker/filters, toaster oven, microwave, 2 burner hot plate (no oven), dishes/pots and pans. There is a loft with an army cot. Not suitable for children under age 5.

Timeless Tides Cottage
This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own private point with 350 feet of waterfront! Cook out on the grill, lounge on the deck or dock while taking in the wildlife on a beautiful tidal river. Watch nesting Bald Eagles and Great Blue Herons fishing! There is plenty of sight-seeing in this picturesque area. Rockland is just 10-minutes away where you can enjoy shopping, restaurants, museums, galleries, lighthouses and festivals.

Authentic Maine Log Cabin | Lakefront | Cozy
Cozy log cabin lake house is perfect for those seeking outdoor recreational adventures visiting Acadia National Park, a relaxing family lake trip, or a true Maine historic log cabin experience. Enjoy this unique home with a spacious waterfront in Bucksport, Maine. Relax in the shade of the tall pine trees, go fishing, or swimming in the lake. When you want to explore, the cabin’s location is perfectly convenient to Bangor, Brewer, Ellsworth, and Bar Harbor!

Sail Loft - Upscale Oceanfront on a Pier near BBH!
Welcome to Sail Loft, a one-of-a-kind vacation destination in Boothbay Harbor! You can't get any closer to the water than this! Imagine relaxing in style and comfort, right over the ocean, and having views from every window. It's like being on a boat but better! Our newly updated, spotless loft has all the amenities you could want, and is only a short walk to downtown. You will find a great mattress, with cozy bedding and fluffy towels.

Parisian apartment in downtown Belfast, Maine
Elegant Parisian-inspired apartment ideal for one couple in the heart of the charming coastal city of Belfast, Maine. Enjoy a stylish, comfortable experience at this central downtown location, steps away from restaurants, shops, and the beautiful waterfront/trail. Free/safe overnight public parking 250 feet away. The bed is made, the table is set, there is a Bluetooth-enabled vintage radio, games, and a smart TV.
Popular amenities for Islesboro waterfront rentals
Waterfront apartment accommodation

Canal View|DTWN Bangor|Steps to great Restaurants

Tapley Farm Waterfront Apartment, Acadia, Pets

Stunning Royal Richmond 2 Br Apartment Get Away!

Union River Retreat Private Apartment

2 bedroom furnished apartment

Downtown waterfront Belfast with amazing views.

Duck Cove Apartment

Oddfellows Hall-Second Floor
Waterfront house rentals

Cove House

Water's Edge-Oceanfront with Stellar View

Cabin on the rocks

Sunny Waterfront Home Overlooking Blueberry Field

Modern Lakefront Home w/ Hot Tub • Winter Escape

Lakefront Log Cabin on Pleasant Lake

The Maine Getaway - Lakefront with Beach

Pinkham Cove - Water Front Cottage
Waterfront condo accommodation

Marina side Stern condo

Oceanfront, dog-friendly 2BR with harbor view

Toddy Haven: A Lakeside Condo Near Acadia.

Mabel's Maine Studio on the River

1BR Waterview | Deck | Partial AC

Best views on MDI 2 bdrm 2 bth condo waterfront

Waterfront|Sunsets|Boothbay Harbor

3-BR Elegant Oceanfront Condo w/ Stunning Views
When is the best time to visit Islesboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $351 AUD | $351 AUD | $351 AUD | $351 AUD | $386 AUD | $421 AUD | $438 AUD | $485 AUD | $421 AUD | $421 AUD | $386 AUD | $414 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 waterfront rentals in Islesboro

Total holiday rentals
Explore 40 holiday rentals in Islesboro

Nightly prices starting at
Islesboro holiday rentals start at $84 AUD per night before taxes and fees

Verified guest reviews
Over 2,090 verified reviews to help you choose

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

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

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

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

4.9 Average rating
Islesboro stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Boston Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Island of Montreal Holiday rentals
- Quebec City Area Holiday rentals
- Halifax Holiday rentals
- Laval Holiday rentals
- Québec Holiday rentals
- Lanaudière Holiday rentals
- Portland Holiday rentals
- Cambridge Holiday rentals
- Rentals with beach access Islesboro
- Rentals with a fire pit Islesboro
- Beachfront rentals Islesboro
- Rentals with a patio Islesboro
- Rentals with a fireplace Islesboro
- Rentals with outdoor seating Islesboro
- House rentals Islesboro
- Rentals with a washing machine and dryer Islesboro
- Apartment rentals Islesboro
- Fitness-friendly rentals Islesboro
- Cottage rentals Islesboro
- Cabin rentals Islesboro
- Family-friendly rentals Islesboro
- Rentals with breakfast Islesboro
- Pet-friendly rentals Islesboro
- Waterfront rentals Waldo County
- Waterfront rentals Maine
- Waterfront 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
- University of Maine
- Rockland Breakwater Light
- Maine Discovery Museum
- Schoodic Peninsula
- Bass Harbor Head Light Station
- Hollywood Slots Hotel & Raceway
- Moose Point State Park
- Maine Lighthouse Museum
- Cellardoor Winery
- Camden Hills State Park




