Vacation rentals in Little Diamond Island

4.88 out of 5 average rating, 258 reviews

An outdoor hot tub is positioned on a patio surrounded by grass and trees. Bubbles rise from the water, creating a serene ambiance. A grill is located nearby, suggesting options for outdoor meals. Views of the surrounding landscape in the background enhance the setting.

Home in Falmouth

Amazing Bay View Home with Hot Tub

This enchanting 2-bedroom home is a coastal dream come true! Luxurious and well-appointed, Casco Bay House sleeps up to six, provides a five-star stay, offers all of the comforts of home AND a relaxing hot tub spa. With stunning views of the water, the house also has easy access to dining, shopping, and sightseeing in Portland's lively Old Port district (just 5 minutes away). Whether you seek quiet tranquility or want to hit the town, this waterside house is the perfect home away from home!

A cobblestone street is framed by historic red brick buildings. Umbrella-covered tables sit outside local shops and cafes. Green and blue storefronts add color, while potted plants enhance the walkways. A friendly atmosphere invites leisurely strolls through the charming neighborhood.

4.98 out of 5 average rating, 150 reviews

Modern Luxury with Bay Views * 5 Star Location!

Well-appointed, high-end private apartment with wide plank pine floors sourced from Western Maine, luxury bathroom and bedroom. Shared patio with grill and fire pit. A short walk to the Eastern Prom or restaurants of the Old Port and Washington Street. I pay attention to details such as cleanliness, local coffee, quality linens, furniture and furnishings. Queen bed with a view of the harbor. This is a non-smoking, non-cooking space. Not suitable for infants children. Hi speed internet.

4.98 out of 5 average rating, 135 reviews

Yurt in Chebeague Island

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled peacefully in a private clearing in the woods. Explore island beaches and hidden trails. This yurt is “glampy” inside with leather chairs and a substantial log bed. The yurt has a rusticator kitchen with all of the basics for cooking, small fridge, stovetop, sink. Water. Outdoor fire pit. WiFi . Check ferry options on Casco Bay Lines or Chebeague Transportation. Host will provide transport to/from ferry to the yurt.

A modern kitchen area is illuminated by natural light streaming through a skylight and a large window. A stainless steel sink is positioned under the window, complemented by wooden counters and open shelving. A single orange chair adds a pop of color, enhancing the minimalist design.

4.98 out of 5 average rating, 151 reviews

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.

4.93 out of 5 average rating, 629 reviews

Adorable getaway on the Eastern Promenade

Lovely third-floor apartment on the East End just steps from the glorious Eastern Promenade. Cozy and cute, this adorable spot resides in the neighborhood which boasts the best restaurants, breweries, and coffee shops in the city all within walking distance. On a quiet residential street, there is plenty of on-street parking. This apartment is on the 3rd floor of the house . **Please note that the last 9 steps leading up to the apartment are quite steep.

Superhost

4.78 out of 5 average rating, 575 reviews

Downtown Studio, Walk Everywhere, Parking

The state of Maine requires all reservations must abide by current state travel restrictions. Please review before booking with us. You will love the location - just park at your reserved spot and forget about it! Great restaurants, bars, coffee shops, museums, Old Port, and Art Districts are all within 20 min walk. Fresh linens, towels, shampoo, french press, an insanely comfortable bed, and warm hospitality are provided, only bring your curious self!

4.92 out of 5 average rating, 282 reviews

A bathroom doorway opens into a compact space featuring a white toilet and a small sink. Light blue walls create a soothing contrast with the warm wood flooring. A mirror and a few shelves are mounted above the sink, providing functional storage.

Guest suite in Portland

Gorgeous Studio 2 Blocks from Eastern Prom!

Located in Portland's trendy East End and within walking distance to the Old Port and Downtown, this beautiful studio is only 2 blocks from the Eastern Promenade and Casco Bay! You will have the Unit entirely to yourself with its own entrance, air conditioning, kitchenette, queen sized bed and an additional pull out single. Easily walk to all of the cool breweries, great restaurants, coffee shops, and night life! Welcome to Portland!

Superhost

A charming beach cottage is nestled in a park-like setting along a quiet road. The ocean is visible in the background, framed by bare trees. The cloudy sky reflects soft shades of blue, while coastal rocks and waves can be seen nearby.

Cottage in Portland

4.85 out of 5 average rating, 148 reviews

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!

Superhost

4.85 out of 5 average rating, 319 reviews

East End Oasis

2bed, 1bath-1st Floor Unit. Located in the middle of Portland's most desirable neighborhood - the top of Munjoy Hill in the East End of Portland. Hardwood floors throughout. The double lot offers a LARGE and PRIVATE fenced in yard, complete with 2 patios/sitting areas, a grill, and beautifully maintained flower/vegetable gardens. Wash & Dryer in Unit. One off street parking spot and city bus stop on the street.

Guest suite in South Portland

A light green door is positioned prominently against a softly painted wall. A small, wall-mounted shelf displays decorative items. Nearby, a wooden dining table with two chairs is illuminated by natural light filtering through a window with light, sheer curtains.

4.92 out of 5 average rating, 255 reviews

Top of the Hill So Po In Law

Lovely In law apartment in desirable Meeting House Hill area of South Portland .We were recently the hottest real estate market in the country .Conveniently located , 10 minutes to Portland , and on the doorstep of local beaches, State parks , restaurants ,unique boutique shops ,amazing bakeries and coffee , lunch and antiquing .All you need for a home away from home . Your going to love this neighborhood !

4.97 out of 5 average rating, 139 reviews

The cabin is surrounded by a winter landscape, showcasing a dark exterior with large windows. Snow covers the ground and roofs, with evergreen trees in the background. A wooden door with a wreath adds a welcoming touch, while a small seating area is visible near the front.

Cabin in Kennebunk

HotTub/5min to K-port, Pet friendly, @anchorunwind

Follow us on IG @anchorunwind. Escape to a hidden gem nestled in the heart of the Kennebunkport area, where modern comfort meets nature's serenity. Our cabin offers an unforgettable vacation experience. ✭"...A must stay location. The host’s were very helpful and genuine..." ✭"...We’ve travelled all around the world and this is in our top 3 Airbnbs we’ve stayed in."

4.96 out of 5 average rating, 134 reviews

The charming exterior of the Tiny Cottage features a vibrant red door and yellow trim. A wooden boardwalk leads to the entrance, framed by lush greenery and flower beds. The cottage is set within a fenced yard, offering a sense of privacy.

Guesthouse in Portland

Tiny Cottage Hideaway, close to everything

A studio built in 1920 turned one-bedroom Guest Cottage, full of charm, on Peaks Island. Within 5 minutes walking distance to the ferry, restaurants, beaches and "Down Front" shops. Perfect for 1-2 people and possibly a third. The 500 square foot Cottage is an off-the-beaten-path Maine experience. Peaks Island is an 18 min ferry ride from Portland.

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Popular amenities for Little Diamond Island vacation rentals

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Free parking on premises

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Other great vacation rentals in Little Diamond Island

The entrance of a historic building is depicted, featuring a large green door with arched windows. Stone steps lead to the door, which is flanked by a tall, narrow window on the left. A lamppost and a small trash bin are visible beside the steps.

4.94 out of 5 average rating, 456 reviews

Beautiful Apt in Historic Building - Old Port

BennettRating, 5 stars2 weeks ago

Great stay at a very nice place. Well located with reasonable parking access.

Private room in Peaks Island

A well-lit staircase is surrounded by light-colored walls and features a polished wooden banister. Framed artwork adorns the walls, while a console table and lamp are positioned near the bottom of the stairs. A patterned rug runs along the floor below.

4.84 out of 5 average rating, 226 reviews

Peaks Island stays with 2 night minimum

LindsayRating, 5 stars2 weeks ago

Lovely home on Peaks Island! Rhonda is such a warm, friendly host and went above and beyond to make sure we had everything we needed during our stay.

A modern building constructed from shipping containers features a combination of black and orange exterior panels. Large glass doors provide entry, and a sign reading 'CHEESE' is prominently displayed. The surrounding area is paved with bricks, creating a welcoming pathway.

4.85 out of 5 average rating, 444 reviews

Modern East End studio, perfect Portland home base

MadisonRating, 5 stars2 weeks ago

Was a great space - very close to restaurants on both sides of Portland!! Munjoy Hill is a great spot!

5 out of 5 average rating, 122 reviews

A view through double glass doors showcases a scenic outdoor space. Lush greenery and flowering plants frame a stone pathway leading to the water's edge. The calm harbor reflects clear blue skies, enhancing the serene atmosphere.

Private room in Portland

Carrabassett Lodge

KarenRating, 5 stars9 months ago

Wow!! Mom and I loved Ella Mae’s place. So private, so comfortable, the best location to the pier and heart of things on the island, and an absolutely stunning , daily sunset view. We had such a relaxing and fun time. Ella Mae couldn’t have been any sweeter or helpful. We really loved everything about our stay at Peaks Island and Ella Mae was just a perfect host. Highly recommend.

A bright bathroom is presented featuring a modern vanity with a circular sink, complemented by a wall-mounted mirror. A glass door shower is visible, surrounded by white walls. Two navy towels hang on polished chrome towel bars, while light streams in through a nearby window.

4.95 out of 5 average rating, 61 reviews

Charming Apartment- Munjoy Hill

RebeccaRating, 5 stars1 week ago

My partner and I loved this Airbnb! Inside was great and it was in a quiet and safe, but still walkable area. We appreciated the local recommendations - the hosts were very helpful!

A cozy outdoor deck is surrounded by greenery, featuring a comfortable chair and an umbrella. A small table with four chairs provides a space for relaxation, while a decorative planter adds a touch of charm. Sliding glass doors lead into the cottage interior.

Cottage in Portland

4.62 out of 5 average rating, 26 reviews

Seaview Cottage/Quintessential Maine With a View

JamisonRating, 5 stars11 months ago

Mary is an excellent host. Very friendly, helpful and responsive. The house was not just clean and comfortable but it was obviously decorated with love and care. The Sun Room was an especially lovely place to be , with amazing views of Great Diamond and the bay…like a private tree house with lots of light. Also, the kitchen was VERY well appointed…great for cooking.. a special nod to the back deck…that’s where to find a cool breeze and a view of the very pretty gardens.

Guest suite in South Portland

A landscaped garden is presented, featuring a variety of shrubs and plants arranged along stone pathways. Fresh greenery is complemented by flares of red flowers. The surrounding neighborhood displays a mix of houses in the background, creating a serene outdoor environment.

4.97 out of 5 average rating, 90 reviews

Ocean Views, work friendly

PaulRating, 5 stars8 months ago

Tom's place was recommended by a third party and we are glad we took their advice. It was everything that was advertised. Easy access from South Portland to all the scenic surroundings, downtown and a wide selection of dining choices. We stayed for two nights and it was a peaceful, relaxing stay. Our trip was in October when the weather was starting to change, did I mention the vibrant colors of the trees, which was a nice change from the heat in Oklahoma.

A bright workspace is created by a wooden desk positioned under three windows adorned with blinds. A blue chair sits at the desk, which is complemented by a small lamp and a potted plant. Natural light illuminates the room, enhancing the serene atmosphere.