
Holiday rentals with outdoor seating in Islesboro
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Islesboro
Guests agree: these rentals with outdoor seating 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.

BREEZE, in a tree The Appleton Retreat
BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE guests may reserve the wood fired cedar hot tub and the sauna, which are close by and private, at an additional charge. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

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

Cozy & peaceful AFrame in Maine woods “Maple”
Come relax in our newly constructed, 4 season modern A frame on the Blue Hill Peninsula. Located in the beautiful town of Brooksville, only 10 mins from Holbrook Island Sanctuary, 15 minute scenic drive to Blue Hill and Deer Isle/Stonington or 1 hour to Bar Harbor/Acadia National Park. Stocked with everything needed to enjoy a relaxing getaway- EV Charger too! Is the property not available when you need it? “Birch” A Frame is just next door. See separate listing for availability OR to book both

Exquisitely Modern Maine Cottage @Diagonair
Romantic and secluded, this 2,000 sf modern luxury cottage nestled on 12 private acres is a favorite of honeymooners and lovers of modern design * 1 hour to Acadia National Park & Bar Harbor; 15 min to shopping, hiking, swimming * Stargazing deck * 2 full baths, one with steam shower * Fully equipped kitchen with and under-counter fridge/freezer * Two gas fireplaces, one indoors, one on a covered deck * Queen bed with luxurious linens and pillows * WIFI, streaming TV, grill, bar * EV charger

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.

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.

Hemlock Cabin.
Nestled in beautiful Hemlock grove is this cozy cabin. Its equiped with all the necessities of home to make your stay comfortable. Guests will have private access to Scammons Pond, also known as, R. Lyle Frost Managment Area. Its a fun place to kayak and fish. From the cabin its about a 45 minute drive to Acadia National Park or Schoodic Point. Besides Acadia, there is local hiking, nearby shopping, local restaurants, the Sunrise Trail, and other Maine adventure just waiting to be explored.

Whitetail by the River, Acadia National Park 10m
Whitetail Cottage - 4 MILES TO MDI- nestled between woods edge & rolling meadows w/views distant views of the Jordan River! Tiny home with WIFI is ONLY 10 MILES to Acadia National Park -a hikers paradise! Minutes to Mount Desert Island but secluded enough to disconnect &get back to nature. Enjoy a stroll to the water, privacy, breathtaking sunsets,stargazing & local wildlife! Perfect for 2 & cozy for 4. Short drive to MDI,Acadia, Bar Harbor,Ellsworth,Southwest Harbor,Shops & Lobster Pound

Little Apple Cabin on 5 acres, amazing stargazing!
Cabins don't come much cuter than Little Apple Cabin. It's as if someone stayed here and *then* invented the word 'CabinCore'. Nestled in the magical woods of Midcoast, Maine, this cabin is the perfect getaway. Located just 25 minutes from the coast, it's the perfect spot for exploring all that the midcoast has to offer. 20 minutes to Camden and Rockland, 25 minutes to Belfast. (No hunting allowed). Surround yourself by the forest, stargaze all night, and rejuvenate in nature.

Modern Tree Dwelling w/Water Views+Cedar Hot Tub
Stay in our custom designed tree dwelling w/ wood-fired cedar hot tub up among the trees! This unique structure is perched atop a 21-acre wooded hill sloping to water views. Enjoy stunning views from the King size bed through a wall of windows. Located in a classic coastal Maine village w/ Reid State Park's miles of beaches + famed Five Islands Lobster Co. (See 2 other tree dwellings on our 21 acre property listed on AirBnb as "Tree Dwelling w/Water Views." See our reviews!).

Spectacular Cottage on Penobscot bay in Belfast
Spectacular cottage on Penobscot bay in Belfast. The cottage is focused on the views from the great room and screened porch. You’ll love the spacious, clean, open cottage with a complete kitchen and propane fireplace. Sit on the porch with a book/glass of wine and watch for seals and schooners. Easy access to the shore along a gradual path and short boardwalk. Great amenities and comfort for vacationers both young and old. Perfect for couples and families (with kids).
Popular amenities for outdoor seating rentals in Islesboro
House rentals with outdoor seating

Cove House

1830s Cape hosted by George & Paul

Hallowell Hilltop Home with Hot Tub & Sauna

Vernon's View

"The Roost" Cottage

Treetop Vista: stunning views, modern farmhouse

Secluded Retreat w/ Luxe Hot Tub & Forest Views

Entire House/Mill/modern vintage on 35 Acre Pond
Apartment rentals with outdoor seating

Tapley Farm Waterfront Apartment, Acadia, Pets

NEW MaineStay near Bangor Airport & Acadia Park

Flower Farm Loft

Coastal Vintage Living

Oceanview Escape near Maine Beaches

Sunny In-Town Camden Studio, 10% weekly discount

Midcoast In-Town Retreat

Lakeside Studio with hot tub, kayaks and canoe
Apartment rentals with outdoor seating

BLUE HILL Village Condo - Great In-Town Location

Battered Buoy - Newly renovated, two bedroom condo

Marina side Stern condo

16 Apartment near Acadia Open Hearth Inn

Modern Condo #3!

Toddy Haven: A Lakeside Condo Near Acadia.

Home away from home cozy new Apartment in Oakland

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 | € 181 | € 185 | € 168 | € 165 | € 175 | € 237 | € 254 | € 254 | € 220 | € 195 | € 178 | € 181 |
| 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 holiday rentals with outdoor seating in Islesboro

Total holiday rentals
Explore 130 holiday rentals in Islesboro

Nightly prices starting at
Islesboro holiday rentals start at € 86 per night before taxes and fees

Verified guest reviews
Over 3,970 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

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




