Photo by Robbie Martin

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Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

Featured Apartments in Great Diamond Island and around

Glorious getaway on Portland's Eastern Promenade.
Property grounds

Glorious getaway on Portland's Eastern Promenade.

10.0 out of 10, Exceptional, (144)
"This rental is adorable with so many thoughtful touches from the host. From the personalized card and snacks to the labels explaining most everything you'd like to know about the space, everything has been considered. A great base from which to explore a fun town."
The price is €214
includes taxes & fees
18 Feb - 19 Feb
Glorious getaway on Portland's Eastern Promenade.
Fall In Love With Portland!
Fridge, microwave, oven, stovetop

Fall In Love With Portland!

9.6 out of 10, Exceptional, (110)
"We had a great time at Nick's apartment, it is spaceous and tastefully furnished. We were able to feel right at home and used the kitchen every day, the dining room had space for all of us which made for some great holiday meals together. The location is nearly unbeatable with just two blocks to the promenade by the water and a short walk to downtown. Congress Street, which is 50 yards from the front door, has a really cool vibe with bars, cafes and restaurants. Yet, you are clearly nestled in a...
The price is €476
includes taxes & fees
18 Feb - 19 Feb
Fall In Love With Portland!
Adorable Portland getaway on the Eastern Promenade
Interior

Adorable Portland getaway on the Eastern Promenade

9.8 out of 10, Exceptional, (93)
"Perfect location. Wonderful accommodations"
The price is €183
includes taxes & fees
18 Feb - 19 Feb
Adorable Portland getaway on the Eastern Promenade
1 room luxury ocean front studio cottage
Miscellaneous

1 room luxury ocean front studio cottage

9.6 out of 10, Exceptional, (149)
"Very clean, amazinv views, perfect weekend!!!! "
1 room luxury ocean front studio cottage
Cozy West End apartment minutes from the Old Port
1 bedroom, desk, iron/ironing board, travel cot

Cozy West End apartment minutes from the Old Port

10.0 out of 10, Exceptional, (5)
"Fantastic hosts and a great place to stay!"
The price is €217
includes taxes & fees
18 Feb - 19 Feb
Cozy West End apartment minutes from the Old Port
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Fridge, microwave, oven, stovetop

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

9.8 out of 10, Exceptional, (103)
"A great place for people looking to explore Portland. Clean, comfortable and with great communication by our host, we’d recommend it for any group looking for a home base in the area."
The price is €476
includes taxes & fees
18 Feb - 19 Feb
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Charming West End Hideaway. Private Parking
Interior

Charming West End Hideaway. Private Parking

10.0 out of 10, Exceptional, (24)
"Communication with the owner was seamless and there were no details missed. The location was perfect for going out and also great if you're looking to shop. The apartment was clean and adorable with a little private balcony. Would definitely stay again!"
The price is €189
includes taxes & fees
18 Feb - 19 Feb
Charming West End Hideaway. Private Parking
Completely remodeled 2 bedroom apartment in Portland's West End
Exterior

Completely remodeled 2 bedroom apartment in Portland's West End

10.0 out of 10, Exceptional, (60)
"We had a very nice stay in this apartment. I would definitely recommend it to others. The owners were friendly and it was easy to get into the unit. The only drawback for anyone who's not quite so agile is the steep staircase to get to the bedrooms. It worked out fine for our family of four, so I just list this for anyone with mobility issues."
Completely remodeled 2 bedroom apartment in Portland's West End
Incredible Location! Heart of Old Port|Roomy Condo
Smart TV

Incredible Location! Heart of Old Port|Roomy Condo

10.0 out of 10, Exceptional, (25)
"Great location for a fun Old Port get away. Property manager was very responsive."
Incredible Location! Heart of Old Port|Roomy Condo
The Portland Getaway
Smart TV, computer monitors

The Portland Getaway

9.6 out of 10, Exceptional, (21)
"This property is well maintained and very clean . Host was easy to communicate with and it was well stocked with basic needs. "
The Portland Getaway
Bright & Sunny West End Apartment with Private Parking.
Interior

Bright & Sunny West End Apartment with Private Parking.

9.8 out of 10, Exceptional, (23)
"This third floor apartment was conveniently located to downtown Portland. There are lots of good restaurants within walking distance. It was spacious and well equipped. It only came with 1 parking space but my son was able to find a spot nearby on the street."
The price is €305
includes taxes & fees
23 Feb - 24 Feb
Bright & Sunny West End Apartment with Private Parking.
Beautiful Old Port Apt-Downtown
Interior

Beautiful Old Port Apt-Downtown

9.6 out of 10, Exceptional, (14)
"It was all terrific. There was one issue with the apartment on the last night but they responded promptly and while it could not be fixed because of the holiday they were attentive and apologetic."
The price is €624
includes taxes & fees
21 Feb - 22 Feb
Beautiful Old Port Apt-Downtown
Prime Downtown Location/Beautiful Brownstone Apt/Sleeps2
Smart TV

Prime Downtown Location/Beautiful Brownstone Apt/Sleeps2

9.8 out of 10, Exceptional, (16)
"Extremely clean, modern and great locattion"
Prime Downtown Location/Beautiful Brownstone Apt/Sleeps2
Historic Home in the West End. Private Parking.
Interior

Historic Home in the West End. Private Parking.

9.8 out of 10, Exceptional, (28)
"We had a lovely stay in this historic home. The decor is charming and original, beds are comfy and everything is clean. The neighborhood is attractive and quiet. The information from the host was helpful. It was great to have a dedicated parking space. As described, the kitchenette has no sink but otherwise is very well equipped for simple food/beverage preparation. We look forward to staying in the future."
The price is €230
includes taxes & fees
18 Feb - 19 Feb
Historic Home in the West End. Private Parking.
Chic One Bedroom Apartment In Portland's Arts District
Fridge, microwave, oven, stovetop

Chic One Bedroom Apartment In Portland's Arts District

10.0 out of 10, Exceptional, (203)
"Sue and Barry were so accommodating, we have never been treated so well staying at a VRBO. They showed us local spots, told us great places for food and drinks, extremely kind and knowledgeable of the area. Couldn’t recommend them enough! "
Chic One Bedroom Apartment In Portland's Arts District
Harborview - Curated East End Escape w/ Parking
2 bedrooms, desk, iron/ironing board, travel cot

Harborview - Curated East End Escape w/ Parking

10.0 out of 10, Exceptional, (2)
"We enjoyed our stay at Jennifer’s place very much .The location was excellent. Walkable distance to the city center and to all the best restaurants.The view was breathtaking and the apartment was amazing!We highly recommend this place. We hope to return soon!"
The price is €570
includes taxes & fees
18 Feb - 19 Feb
Harborview - Curated East End Escape w/ Parking
Newly Furnished One Bedroom Just Steps to Ferry Beach
Beach nearby, sun-loungers, beach towels

Newly Furnished One Bedroom Just Steps to Ferry Beach

10.0 out of 10, Exceptional, (57)
"Impeccably clean and small dog friendly garage apt. We enjoyed our long weekend at Camp Ellis. The apt was very clean and such a calm and peaceful ambiance. The decor/aesthetic is soft and calming. Bed is on the harder side (maybe a topper?!) but perfect place and would return. "
Newly Furnished One Bedroom Just Steps to Ferry Beach
East end. Walk to food, beer and downtown fun.
TV

East end. Walk to food, beer and downtown fun.

9.8 out of 10, Exceptional, (23)
"Our host was an excellent, prompt communicator. He even offered information about things to do in the area. He was very clear about expectations about our stay which at first was a little off-putting. Cooking no greasy food seemed a little much and had us wondering what was allowed. The property was well stocked and as described including the slanted floor. We weren’t aware at booking that parking was only on the street. That would have been nice to know. It’s a 20 minute walk to downtown which...
The price is €464
includes taxes & fees
16 Mar - 17 Mar
East end. Walk to food, beer and downtown fun.
Old Orchard Beach Apartment - Quick Walk to Beach!
Toaster, dining tables

Old Orchard Beach Apartment - Quick Walk to Beach!

9.4 out of 10, Exceptional, (20)
"Great location to walk to the beach or to the pier. The top floor requires many steps so if you have a hard time with mobility this would not work for you. We loved it! So clean and well stocked with dishes, appliances and cookware. The recliners are the bomb! Bed was comfortable as well. Two air conditioners which kept us comfortable. The site is on point with their description and photos."
Old Orchard Beach Apartment - Quick Walk to Beach!
Superb Location!! Heart of Old Port/Spacious Condo
TV, books

Superb Location!! Heart of Old Port/Spacious Condo

9.8 out of 10, Exceptional, (19)
"This was our second stay at Dena’s property. Perfect size, 3bedrooms and 3 baths. This unit is impeccable, very clean, spacious, and well stocked. Dena checked in with us to be sure we were able to check in easily and was very responsive to anything we needed. We were located in the center of everything. Easily walkable area. We loved our stay and would love to return! "
Superb Location!! Heart of Old Port/Spacious Condo
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Great Diamond Island

The Weldon Hotel
Deluxe Suite, 2 Bedrooms | Private kitchen

The Weldon Hotel

4.0 star property
9.4 out of 10, Exceptional, (36)
"The full kitchen and appliances were perfect for my stay so that I did not have to eat out while I was there and save money "
The price is €151
includes taxes & fees
2 Mar - 3 Mar
The Weldon Hotel
Gorgeous ocean-front home with stunning beach views
On the beach

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (101)
"We stayed to visit family in the area. The location was excellent and we loved the ocean view. Everything was very clean, except under the sofa in the living room. We searched for a dropped puzzle piece and "
Gorgeous ocean-front home with stunning beach views
100 feet from the ocean 3 bedroom cottage 420 friendly
Interior

100 feet from the ocean 3 bedroom cottage 420 friendly

8.6 out of 10, Excellent, (16)
"Owner should get new cleaners. House smelled like dog urine. Bathroom smelled like human urine. Had to clean floors and bathroom…lots of dirt…not sure the last time floors were I’m mopped. Dog hair on sheets. Beds were not comfortable so be prepared. Parking is a challenge. One paid parking spot in front ($36/day). Can park super close to house for 2nd spot. Owner not very responsive. Had to constantly message for arrival info and didn’t get it until 10 mins after checkin time. No instructions...
100 feet from the ocean 3 bedroom cottage 420 friendly
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.