Vacation rentals in Long Island

4.92 out of 5 average rating, 304 reviews

A serene vista showcases the city skyline reflected in calm waters, framed by lush green grass and trees. The scene captures a tranquil moment, inviting viewers to appreciate the natural beauty and urban blend surrounding the space.

Home in Portland

Top Deck - Portland Property with Views!

Views, Views, Views! 2 huge decks overlooking water and city skyline. This home is adjacent to Payson’s Park – Portland’s largest park. 5-7 min ride to downtown Portland and the Old Port’s fabulous bars and restaurants. The main floor has bedroom with bath, kitchen, and living room. The upstairs has a large bedroom with bath, open room that can be used as 2nd living room or a 3rd/4th bedroom space. Sleeps 10-12. Off street parking 6-8. Large yard. Portland License #STHR-002587-2020

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4.91 out of 5 average rating, 602 reviews

A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.

Treehouse in Sanford

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

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4.97 out of 5 average rating, 301 reviews

Cottage in Portland

4br2ba House+parking@PeacefulOasis on Munjoy Hill

This standalone 1500sf 3-story cottage is set in an ideal location, close to the Eastern Prom, cafes, award-winning restaurants, breweries and the Old Port. -Main floor: well-equipped kitchen + open concept living/dining room -Upper floor: 3BR (1 queen, 1 full, 1 twin) + bath -Garden level: 1BR/1 bath (queen) with private entrance - Off-street parking for 1 car This charming home @ A Peaceful Oasis offers plenty of space, privacy & comfort, making it the perfect home base for your stay.

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Superhost

A charming red cottage is nestled among greenery, featuring a wrap-around porch with multiple entry points. The house, with a sloped roof and white trim, is set against a backdrop of tall trees and a grassy lawn, creating a serene outdoor setting.

Cottage in Long Island

Maine island vacation cottage

Just off the coast of Portland, Maine in the Casco Bay, lies Long Island, where our charming Long island get-away cottage is located. It is our own family vacation home that we love dearly and are happy to share with guests. Enjoy a long Fall weekend, or relaxing summer vacation week ...or two. Slow down and unwind on the thirty minute ferryboat ride to Long Island. Enjoy the beautiful beaches and quiet island life. It’s great for kids of all ages, and only a two hour drive from Boston.

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4.61 out of 5 average rating, 61 reviews

5.0 out of 5 average rating, 152 reviews

The exterior of the A-frame cabin is showcased, featuring a unique wooden facade and metal roof. Sunlight streams through tall triangular windows, illuminating the surrounding wooded area. A gravel path leads to the entryway, enhancing the cabin's connection to nature.

Cabin in Freeport

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

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Apartment in Peaks Island

A bright hallway leads into the living space, featuring light wood flooring and white walls. A dining area is seen to the left with a small table and chair, while decorative elements, including potted plants and books, add character to the space.

Peaks Island Master Bedroom Suite

Enjoy your stay at this conveniently located, light-filled, modern, chic living space--only a 4-minute walk from ferry, great sunsets, close to market and restaurants with a private entrance and deck. Walking distance to the best island beaches. Located on a quiet, dead end road off the main street. The space is found at the rear of one of Peaks Island's most beautiful, original Cape homes. Guests can enjoy a comfy queen size bed, organic cotton sheets, and a pull-out sofa bed.

ValueFamilyAir conditioning

4.99 out of 5 average rating, 229 reviews

4.87 out of 5 average rating, 185 reviews

Year-Round: Peaceful and Quiet Island Getaway

*Quiet and Peaceful *Easy Portland Access *Sparkling Bathroom Remote Downeast island experience just two hours from Boston ... Renovated home in the tranquil Tolman Heights section of Peaks (the island’s highest point) offers a modern kitchen and sparkling new bathroom. Sleeps 6-plus comfortably in bedrooms all equipped with ceiling fans. Spacious home is a short stroll to the Back Shore, with its dramatic views of Casco Bay and the open ocean. STHR-007313-2025

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Apartment in Downtown Portland

A modern lounge area is highlighted by large skylights, allowing abundant natural light to fill the space. A sleek, white sectional is complemented by colorful accent pillows and a patterned area rug. Exposed brick walls add an element of rustic charm, with scenic views of the harbor visible through the glass.

Old Port Penthouse Suite - Amazing Harbor Views

CO2024-01992 Private Old Port Penthouse w/Breathtaking Views + Your Own Cupola. Quiet + Secure. Gorgeous contemporary suite full of light located right across from the working waterfront. Lobster and seafood off the boat is 100 meters from your front door. Watch the ferries to the islands from the cupola. Smell the salt air from your private deck. Welcome to Portland! Please note: animals (including assistance animals) not allowed due to owner's health.

ValueFamilyOutdoor spaces

4.97 out of 5 average rating, 327 reviews

4.84 out of 5 average rating, 164 reviews

A charming beach cottage stands in a serene setting, featuring a weathered wooden exterior with red-trimmed windows. A yellow door welcomes guests, while a wooden staircase leads to the entrance. Lush greenery and colorful flowers surround the home, indicating a well-tended garden.

Cottage in Peaks Island

Artist's Retreat

A 1900's beach cottage on Peaks Island, a 5 minute walk from the ferry, but nestled off the road in a park like, peaceful setting. Hear the waves at night from the backyard, walk 5 minutes to Sandy Beach for swimming and to Picnic Point, with its view of Cushing Island and Whitehead Pass. Experience the beauty of Peaks -- but take a 17 minute ferry ride into downtown Portland for award winning restaurants. The best of both worlds!

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4.98 out of 5 average rating, 240 reviews

A well-maintained cottage is positioned beside a tranquil body of water, surrounded by lush greenery. A spacious lawn is visible in the foreground, showcasing an outdoor seating area with a patio umbrella. The scenic view of the water complements the serene setting.

Home in Harpswell

Waterfront Cottage On Basin Cove - Amazing Sunsets

Bright, airy cottage right on Basin Cove,a tidal cove in Harpswell Maine. Cool breezes with pristine views, especially for the sunsets over the cove. At the end of Harpswell Neck, so it feels like you're far away, but still only an hour from Portland, 1/2 hour from Freeport & 15 minutes from Brunswick. Use it as your hub to explore Midcoast Maine or hunker down and enjoy the screened in porch after a swim in the cove.

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4.99 out of 5 average rating, 76 reviews

A spacious house with large glass windows is featured, set against a colorful sunset sky. A wide deck extends around the home, with black outdoor furniture positioned for views. The structure is framed by trees and a grassy area, providing a serene atmosphere.

Home in Long Island

Whole house on a great island in Casco Bay!

Nona's View is a beautiful spot located on Long Island, Maine in Casco Bay. Long Island is only a 45 minute ferry ride from Portland and this quiet island is great for anyone looking to get away from the stress of the mainland. You will see breathtaking sunsets and will have access to the best beaches in the bay! The house also comes with a golf cart to use during your stay and will be left at the dock for you.

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A scenic view of the ocean framed by green trees and a grassy area. A distant lighthouse is visible on the horizon, while the sky is partly cloudy, creating a peaceful atmosphere. The landscape includes several large rocks scattered across the lawn.

4.9 out of 5 average rating, 123 reviews

Stunning Ocean Views From This Peaks Island Home

Completely remodeled classic Peaks Island home with stunning Atlantic Ocean white water views. Welcome to the newly renovated Valhalla on Peaks. This classic home underwent a complete renovation for your family's enjoyment. From the minute you step onto the property, your senses will be overwhelmed by the views, ocean breeze, salty smell, and the property's nostalgic feel.

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Popular amenities for Long Island vacation rentals

Monthly stays

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Long Island

4.82 out of 5 average rating, 51 reviews

A charming cottage exterior is highlighted by vibrant flowerbeds featuring yellow, pink, and blue blooms. A large deck is visible, complemented by a patio umbrella. The home's red facade and white railings create a welcoming atmosphere, surrounded by lush greenery.

Cottage in Long Island

Picturesque Maine water view Long Island

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4.93 out of 5 average rating, 29 reviews

Home in Long Island

Magical Long Island Retreat | Steps to Quiet Beach

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5.0 out of 5 average rating, 38 reviews

A large window frames the ocean view, where waves gently roll towards rocky outcrops. A cozy seating area, featuring a leather sofa and a wooden coffee table, is positioned to allow for a serene observation of the changing tides.

Home in Cape Elizabeth

"Periwinkle" ~ a Charming Oceanfront Cottage

LocationFamilyAccess

5.0 out of 5 average rating, 16 reviews

Home in Freeport

Mermaid's Chair | Private Beach | Hot Tub

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4.97 out of 5 average rating, 35 reviews

A dining table is set with a bowl of fresh salad, complemented by a glass of red wine. In the background, the sun sets over the water, casting a warm golden light through large windows that frame the peaceful waterfront view.

Home in Harpswell

Sunset Stunner w/summer dock

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Superhost

5.0 out of 5 average rating, 4 reviews

Unbeatable view! Peaceful spot.

LocationFamilyAccuracy

5.0 out of 5 average rating, 74 reviews

A spacious living area showcases a light-colored sofa paired with a wood coffee table, surrounded by hardwood flooring. Natural light floods in through the windows, highlighting the open layout that connects to the kitchen area featuring wooden cabinets and modern appliances.

Cottage in Peaks Island

Classic Peaks Island Cottage - 5 min walk to Ferry

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A modern cottage is positioned on a gently sloping landscape, showcasing large windows that maximize natural light. Surrounding gardens display vibrant flowering plants, creating a tranquil outdoor setting. The cottage features a charming architectural design with a blend of vertical and horizontal siding.