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

Waterfront Guest House on the Maine Coast
Bright open four-season guest house with fantastic view of Jones Cove and the open ocean in beautiful South Bristol, Maine. The guest house offers privacy and independence. The top floor has an open space with kitchen, sleeping area with queen bed, bathroom. The ground floor has a desk, Smart TV, seating area and French doors that open onto a stone patio. Includes Kohler generator, fiber optic wifi, outdoor grill & fire pit. The water is tidal Owner lives on property (150 ft from guest house)

Cozy Cottage on the Penobscot — Panoramic Luxury!
Escape to your private sanctuary where tranquility meets luxury. Our Coastal Maine Cottage home is perched on a granite ledge that disappears twice daily with the rising tide. Enjoy the pristine interior bathed in natural light, cherry floors, and gourmet kitchen. Wake to panoramic views of the Penobscot River from the owner's suite. Conveniently located 12 minutes to downtown Bangor, our retreat offers easy access to urban amenities, an international airport, and Acadia! IG @cozycottageinmaine.

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.

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.

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.

Private Sauna+Beach/Hiking Close+FirePit+S'mores
Come relax and unwind at Pine Cabin! * Private Cedar Sauna w/Glass Front * Minutes to Reid State Park Beach & 5 Island🦞 * Fire Pit w/S'mores * 100% Cotton sheets/towels * Rain Shower & Heated Bathroom Floor * AC/Heat & Automatic Kohler Generator * SmartTV & Record Player w/Vinyl *Fast Broadband Wifi *Pine Cabin is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart and separated by a privacy screen and natural landscaping.

Call of the Loon - Water Edge Lake House
Escape to serenity and immerse yourself in the breathtaking sunsets of Fernald's Neck Preserve at our lakeside home on Lake Megunticook, situated just a stone's throw away from the charming town of Camden. Indulge in the magic of Lake Megunticook, explore the nearby hiking trails or simply unwind on the porch with a good book and a view that never ceases to amaze. Book your stay at the Lake House today, and let the tranquility of this retreat wash away the stresses of everyday life.

Beachfront Guest Cottage - Year-round Hot Tub!
Our cozy guest cottage has easy beachfront/kayak/canoe access, and is located very close (within walking distance at low tide) to the public boat launch for larger boats. Great location to explore Deer Isle, Acadia (approx 1hr), Castine (45m), and the Bangor (1hr) area. Brave children and adults even swim from the beach but comfortable swimming ponds/lakes are 10m in several directions. The hot-tub is open year-round! Additional guests can be considered prior to booking.

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.

The Tiny House with the Enormous View of Acadia
The Tiny House on Goose Cove is the perfect place from which to enjoy your visit to Acadia National Park. Set on three acres of shore front property, the house features spectacular views of Mount Desert Island. The entrance to the Park, and the shops and restaurants of Bar Harbor, are just 20-25 minutes away by car. And when you've had enough of the bustle and crowds, you can retreat to the peace and serenity of this beautiful property.

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.

Quiet lakefront cottage on Graham Lake
Waterfront cottage on quiet Graham lake in the middle of our small working farm. Great spot for quiet relaxation, fishing or kayaking. 2 canoes on the property. Good central location for visiting Bangor, Bar Harbor, Acadia National Park and Downeast Sunrise ATV Trail. Private setting. Wifi available at the farmhouse. Because of family allergies, we cannot host pets
Popular amenities for waterfront rentals in Islesboro
Waterfront apartment rentals

Canal View|DTWN Bangor|Steps to great Restaurants

Tapley Farm Waterfront Apartment, Acadia, Pets

Coastal Loft Apartment with Beach Access

Union River Retreat Private Apartment

Downtown waterfront Belfast with amazing views.

Sail Loft - Upscale Oceanfront on a Pier near BBH!

Duck Cove Apartment

Oddfellows Hall-Second Floor
Waterfront house rentals

Cove House

Waterfront near Acadia | Hot Tub| Kayaks| Bay View

Gran Den Lakefront Home Near Acadia

Water's Edge-Oceanfront with Stellar View

Cabin on the rocks

Lakefront: Private Hot Tub, Sauna & Free Massages!

Sunny Waterfront Home Overlooking Blueberry Field

The Ward House
Waterfront apartment rentals

Marina side Stern condo

Oceanfront, dog-friendly 2BR with harbor view

Oceanfront Multi-level Condo with Prime Amenities

Toddy Haven: A Lakeside Condo Near Acadia.

1BR Waterview | Deck | Partial AC

Best views on MDI 2 bdrm 2 bth condo waterfront

2BR Condo + Ocean Views in Downtown SW [Seaglass]

Waterviews + Sunsets + Boothbay/Gardens Aglow
When is the best time to visit Islesboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 216 | € 216 | € 216 | € 216 | € 237 | € 259 | € 264 | € 259 | € 259 | € 259 | € 216 | € 216 |
| 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 € 121 per night before taxes and fees

Verified guest reviews
Over 1,960 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Islesboro holiday rentals include wifi 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!
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- Waterfront rentals Waldo County
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- Waterfront rentals United States
- Acadia National Park
- Pemaquid Beach
- Northeast Harbour Golf Club
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- Hermon Mountain Ski Area
- Dragonfly Farm & Winery
- Sandy Point Beach
- Bear Island Beach
- Sand Beach
- Lighthouse Beach
- Kebo Valley Golf Club
- Eaton Mountain Ski Resort
- Pebbly Beach
- The Camden Snow Bowl
- Wadsworth Cove Beach
- Farnsworth Art Museum
- Narrow Place Beach
- Spragues Beach
- Three Island Beach
- Driftwood Beach
- Rockland Breakwater Light
- Islesboro Town Beach
- Hero Beach