
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$25,117 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.
LocationFamilyCondition
4.98 out of 5 average rating, 280 reviews
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
FamilyValueBathroom
5.0 out of 5 average rating, 168 reviews
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.
LocationFamilyDecor
4.95 out of 5 average rating, 175 reviews
"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
LocationValueComfort
4.94 out of 5 average rating, 107 reviews
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.
FamilyLocationWalkability
5.0 out of 5 average rating, 239 reviews
[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.
ValueLocationKitchen
4.93 out of 5 average rating, 259 reviews
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.
FamilyLocationAccuracy
4.92 out of 5 average rating, 125 reviews
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.
ValueFamilyGetting around
4.93 out of 5 average rating, 123 reviews
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.
FamilyLocationAir conditioning
4.94 out of 5 average rating, 103 reviews
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.
FamilyValueOutdoor spaces
4.95 out of 5 average rating, 325 reviews
MASSIVE Oceanfront Dark Harbor Home on ISLESBORO
This elegant 5+ bedroom Victorian Cottage has been carefully restored and renovated to highlight the natural charm and character of the home while integrating sophisticated elements throughout. Prime location within walking distance to local coffee shop, ice cream parlor and charming gift shop. All points of island are within a 10 minute drive of the home. Massive, private bedrooms perfect for multiple couples or families. Reach out with any questions or concerns you may have!
LocationFamilyOutdoor spaces
5.0 out of 5 average rating, 26 reviews
Historic Camden Farmhouse • Pets Welcome
Charming 1820s farmhouse just one mile from downtown Camden, the harbor, and Camden Hills State Park. Listed on the National Register of Historic Places, this unique home blends historic New England character with modern comfort. Enjoy cozy, welcoming spaces after hiking Mount Battie, sailing Penobscot Bay, or exploring Camden’s shops and restaurants. Pet- and family-friendly, with room to relax, unwind, and experience authentic coastal Maine living in every season.
ValueLocationTV
4.89 out of 5 average rating, 127 reviewsPopular amenities for Islesboro house rentals
House rentals with a pool

Large private area, close to Rockland
FamilyLocationPool
4.94 out of 5 average rating, 116 reviews
Cozy, fun, 3 bedroom home with a pool and Hot Tub.
ValueLocationHospitality
4.97 out of 5 average rating, 372 reviews
Coastal Retreat with Pool and Cheerful Vibes
LocationFamilyLong stay
4.86 out of 5 average rating, 22 reviews
Gorgeous house with a view
FamilyLocationNearby
5.0 out of 5 average rating, 46 reviews
Dog Friendly Midcoast Cape
LocationValueCleanliness
4.94 out of 5 average rating, 72 reviews
Ocean View Retreat with Heated Pool / Hot Tub
FamilyLocationGrill
4.95 out of 5 average rating, 75 reviews
Large MDI house w/pool perfect for groups+families
ValueLocationNearby
4.71 out of 5 average rating, 51 reviews
New Boho Cape with Pool! Fenced yard, pet friendly
FamilyValueTV
4.96 out of 5 average rating, 80 reviewsWeekly house rentals

Antique Barn Apartment at Salt Water Farm
FamilyLocationLaundry
5.0 out of 5 average rating, 65 reviews
Cliff House - Ocean Views! Architectural designed.
ValueLocationLayout
4.98 out of 5 average rating, 55 reviews
#1 NE Small Coastal Town- Castine, Shell Cottage
LocationFamilyWalkability
5.0 out of 5 average rating, 39 reviews
Casa on the Bagaduce River
FamilyLocationAccess
5.0 out of 5 average rating, 45 reviews
Spacious Oceanfront Home Stunning Sunset Views
FamilyValueComfort
4.96 out of 5 average rating, 26 reviews
Sweeping Views with Private Beach in Castine
LocationValueParks
4.92 out of 5 average rating, 74 reviews
NewerConstr.4bed coastal home near Camden w/firept
ValueFamilyNearby
4.95 out of 5 average rating, 21 reviews
Oceanfront home in Castine
ValueLocationQuiet
4.9 out of 5 average rating, 31 reviewsPrivate house rentals

Above & Beyond: Beautiful home on Penobscot Bay
LocationValueGrill
4.97 out of 5 average rating, 77 reviews
New! Centrally located on MDI, near Lakes/Acadia
LocationFamilyCheckout
5.0 out of 5 average rating, 10 reviews
4bed Full House on Private Dr. w/ Large Yard
FamilyLocationKitchen
4.99 out of 5 average rating, 77 reviews
Hot Tub, MDI, Lake front, Fire pit, Game Room!
FamilyValueGrill
5.0 out of 5 average rating, 28 reviews
Waterfront Home in Heart of Town
LocationFamilyComfort
4.93 out of 5 average rating, 28 reviews
Cozy Coastal New England Farmhouse
FamilyValueDecor
4.79 out of 5 average rating, 75 reviews
Waterfront, Meadows: 10 acres+ a Spacious House
ValueFamilySleep quality
4.99 out of 5 average rating, 97 reviews
Dockside Oasis
ValueFamilySleep quality
4.96 out of 5 average rating, 67 reviewsWhen is the best time to visit Islesboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$52,328 GYD | G$73,259 GYD | G$52,328 GYD | G$52,328 GYD | G$36,002 GYD | G$73,259 GYD | G$73,259 GYD | G$73,259 GYD | G$72,213 GYD | G$70,538 GYD | G$61,747 GYD | G$47,095 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 |
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- 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
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