Holiday rentals in Little Diamond Island

4.88 out of 5 average rating, 258 reviews

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!

4.94 out of 5 average rating, 247 reviews

Guest suite in Falmouth

Pristine Waterfront Studio Apt. Retreat

Studio apt. on the water where Casco Bay meets the Presumpscot River. Downtown Portland 2 minutes away. Perfect to... *Relax & enjoy the sunset & water views from decks *Head into Portland-Bon Appetite 2018 Restaurant City of the Year & "The Best Lobster Roles in Maine" *CNN named Portland as "one of the best towns to visit in 2024" *Drive up the coast, explore the beautiful beaches, lighthouses, quaint towns *Adventure inland for amazing hikes & mountainous views *Awesome music scene!

4.94 out of 5 average rating, 142 reviews

Flat in South Portland

Sopo Abode

Welcome to your garden oasis. Your home away from home. This elegantly styled garden level apartment in South Portland's crown jewel neighborhood, Sylvan Sites, is spacious, calm, and inviting. Have a sit in your private sauna, and take in the abundant birdsong of the neighborhood from your private back patio while you sip your morning coffee. Just down the road (5 minutes) to downtown Portland, Willard Beach, or Knightville, and 10-15 minutes to Scarborough and Cape Elizabeth beaches.

4.98 out of 5 average rating, 154 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.

4.82 out of 5 average rating, 486 reviews

Walk-able Portland Studio

NEWLY RENOVATED! Cozy studio apartment in a historic building, located in Portland's East End Neighborhood. This location can't be beat! The Space features original hardwood floors, and large windows, subway tiled shower and thoughtful decor. Portland Food Co-Op is directly next door, as is the Walgreen's. Walking distance to Eventide, Honey Paw, Duck Fat, Hugos, Little Woodfords, LB Kitchen, Washington Ave Breweries and Distilleries and Old Port shopping district.

4.9 out of 5 average rating, 108 reviews

Portland Back Cove Hideaway-1 BR- With Patio

Our quiet residential Back Cove neighborhood is your perfect retreat from a busy day exploring Portland. Take a short drive to the center of the city, or enjoy the waterfront walking and biking trail which loops around the cove. Dine at Tipo or Woodford F&B, two neighborhood favorites. Come home to this newly renovated space and relax on the patio! Our space can accommodate four guests. Great for a family, or close friends! We look forward to hosting you!

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, 577 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!

Guest suite in South Portland

5 out of 5 average rating, 253 reviews

Bright Guest Studio Near Lighthouses and Beach

This bright guest studio is steps from the Greenbelt Walkway. Walk (within 10 mins) to two lighthouses, Willard beach, Bug Light Park, Scratch Bakery, Willard Scoops ice cream and a variety of restaurants. Portland is an 8 minute drive or 20 minute bike over the bridge. The space is minimal, bright and airy with windows surrounding, an elevated bed with comfy queen mattress, fully equipped kitchen, washer/dryer, and cozy couch for lounging.

4.92 out of 5 average rating, 282 reviews

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!

4.96 out of 5 average rating, 480 reviews

Tiny home in Portland

The Garden Cabin Tiny Home

Curious about tiny homes? Love dogs, gardens, pine trees, campfires, and birds? Hate cleaning fees? Our private 128 sqft cozy cabin is for you! On the spectrum between camping and a hotel room, it's a chill place to call home while visiting Portland. Enjoy our garden while sipping a beverage from your own deck or around the campfire. Heat and A/C when needed. Please, no smokers, kids under 13, or guest pets. STHR-000718-2018

4.97 out of 5 average rating, 574 reviews

Cozy & Comfortable apartment in a perfect location

Bright sunny 1 bedroom private apartment in a quiet, Owner Occupied building. Perfect location. A short walk to Duckfat, Eventide and the rest of Portland. Top floor with full kitchen, work/desk area, comfortable living room, full bath with tub and shower, bedroom with a comfortable Queen bed. If you're a book lover, you'll enjoy it even more! Includes Reserved off street parking. Portland City License #STHR-000980

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Popular amenities for Little Diamond Island holiday rentals

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Other great holiday rentals in Little Diamond Island

Private room in Peaks Island

4.84 out of 5 average rating, 226 reviews

Peaks Island stays with 2 night minimum

LindsayRating, 5 stars3 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.

4.85 out of 5 average rating, 445 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

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.

4.89 out of 5 average rating, 626 reviews

Private room in Portland

Large, spacious, and eclectic Room, Private Bath

SaraRating, 5 stars1 day ago

We had a wonderful stay at Gail's place. Very peaceful and relaxing space. At Gail's suggestion we walked to a local noodle bar and had a fantastic dinner! Gail was warmly welcoming and helpful. We thoroughly enjoyed our stay with her!

Cottage in Portland

4.62 out of 5 average rating, 26 reviews

Seaview Cottage/Quintessential Maine With a View

JamisonRating, 5 stars12 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.

Superhost

Hotel room in Portland

4.87 out of 5 average rating, 463 reviews

Eateries, nightlife, galleries – walk to it all

JackieRating, 5 stars3 days ago

Our stay at the Aloft was amazing! Location was great and walking distance to so many restaurants, bars, shops. All the staff were very nice! Would love to stay here again

Guest suite in South Portland

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.