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

Total vacation rentals
Explore 120 vacation rentals in Islesboro

Nightly prices starting at
Islesboro vacation rentals start at G$25,105 GYD per night before taxes and fees

Verified guest reviews
Over 2,050 verified reviews to help you choose

Family-friendly vacation rentals
100 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 70 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
110 of Islesboro vacation 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.
ValueFamilyAir conditioning

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
FamilyValueRiver

Coveside Lakehouse on Sandy Point
If you are looking for a beautiful vacation spot on Green Lake, look no further. Cove Side Lake House on Sandy Point is the perfect place for you and your whole family to enjoy the lovely Maine summer, from sunrise until sun set. Whether you enjoy relaxing on the deck, catching a nap in the hammock, or fishing and kayaking, this is the vacation destination you've been dreaming of. Green Lake, located in Ellsworth/Dedham Maine, is a 3,132 acre freshwater lake with a maximum depth of over 170ft.
FamilyValueKitchen

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.
ValueLocationIndoor spaces

"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
FamilyLocationCleanliness

Quaint 3 Bedroom In Town Camden Home
Our 1900’s New England style home is located in a quiet neighborhood less than a mile from the heart of downtown Camden. Midcoast Maine is home to many great restaurants, shops, and art galleries, as well as events such as the National Toboggan Championships, North Atlantic Blues Festival, Maine Lobster Festival, and more! With Rockland just a quick 15 min. drive and Belfast located approximately half an hour north, you’ll be in a prime location to experience everything this area has to offer.
ValueFamilyWalkability

[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.
LocationValueHospitality

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.
LocationFamilyLong stay

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.
FamilyValueRiver

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.
FamilyLocationComfort

Blue Heron
Blue Heron, recently renovated with modern amenities, is conveniently located near local art, culture, restaurants, and fine dining. Its beautiful Burnt Cove sunsets, peaceful private settings, and natural ambiance make it a favorite among couples, solo adventurers, and families. The spacious front lawn offers ample space for relaxation. Just a short walk away, you can enjoy a lobster bake on the shore, launch your kayak in the backyard, or explore the local shops within a mile’s reach.
FamilyValueOutdoor spaces

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 Please read “other details”, we are on an island.
LocationValueHeating
Popular amenities for Islesboro house rentals
House rentals with a pool

Large private area, close to Rockland
FamilyValueQuiet

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

Gorgeous house with a view
LocationFamilyIndoor spaces

Coastal Retreat with Pool and Cheerful Vibes
LocationFamilySleep quality

Indoor Pool*Hot Tub*Sauna*Game Room*Near Acadia
LocationFamilyGetting around

The Jarvis Homestead | Historic Maine Mansion
FamilyValueWifi

Ocean View Retreat with Heated Pool / Hot Tub
LocationFamilyNearby

Dog Friendly Midcoast Cape
ValueFamilyCleanliness
Weekly house rentals

MASSIVE Oceanfront Dark Harbor Home on ISLESBORO
FamilyLocationBeach

Double On The Rocks, ocean view family retreat
FamilyLocationSleep quality

Antique Barn Apartment at Salt Water Farm
FamilyLocationLong stay

Cliff House - Ocean Views! Architectural designed.
ValueLocationKitchen

Casa on the Bagaduce River
FamilyValueSleep quality

#1 NE Small Coastal Town- Castine, Shell Cottage
LocationFamilyView

Above & Beyond: Beautiful home on Penobscot Bay
ValueFamilyLong stay

Stonington Dream House
LocationFamilyWifi
Private house rentals

Island View Cottage - NEW! Waterfront Home in LDI
ValueFamilyComfort

New! Centrally located on MDI, near Lakes/Acadia
FamilyLocationCheck-in

Dockside Oasis
LocationValueIndoor spaces

NewerConstr.4bed coastal home near Camden w/firept
FamilyLocationWifi

Hilltop Retreat
LocationFamilyTV

Waterfront Home in Heart of Town
LocationFamilyBackyard

Oceanfront home in Castine
LocationValueAir conditioning

Bay View Cottage · Prime Camden · Walk to Harbor
ValueLocationDecor
When is the best time to visit Islesboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$52,303 GYD | G$73,224 GYD | G$52,303 GYD | G$52,303 GYD | G$35,984 GYD | G$73,224 GYD | G$73,224 GYD | G$73,224 GYD | G$72,178 GYD | G$70,504 GYD | G$61,717 GYD | G$47,072 GYD |
| 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
- Montreal Vacation rentals
- Boston Vacation rentals
- Quebec City Vacation rentals
- Portland Vacation rentals
- Providence Vacation rentals
- Salem Vacation rentals
- Newport Vacation rentals
- Halifax Vacation rentals
- York County Vacation rentals
- Bar Harbor Vacation rentals
- Cambridge Vacation rentals
- New Haven Vacation rentals
- Rentals with beach access Islesboro
- Waterfront rentals Islesboro
- Beachfront rentals Islesboro
- Cabin rentals Islesboro
- Family-friendly rentals Islesboro
- Pet-friendly rentals Islesboro
- Apartment rentals Islesboro
- Rentals with breakfast Islesboro
- Cottage 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
- Schoodic Peninsula
- The Camden Snow Bowl
- University of Maine
- Rockland Breakwater Light
- Sand Beach
- Camden Hills State Park
- Farnsworth Art Museum
- Maine Lighthouse Museum
- Moose Point State Park
- Cellardoor Winery
- Bass Harbor Head Light Station
- Hollywood Slots Hotel & Raceway
- Echo Lake Beach





