Photo by Robbie Martin

Great Diamond Island Vacation Rentals

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Tonight
Jan 29 - Jan 30
Tomorrow
Jan 30 - Jan 31
This weekend
Jan 31 - Feb 2
Next weekend
Feb 7 - Feb 9

Vacation Rentals 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, (35)
"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 CA $245
CA $268 total
includes taxes & fees
Feb 5 - Feb 6
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, (100)
"The view and location are amazing. The house was very comfortable for the three adults on our trip. It’s also very suitable for a family with kids as one of the rooms has two bunk bed sets. It’s comfortable, cozy, and completely relaxing. Within walking distance of the pier and entertainment. Great place to stay. "
Gorgeous ocean-front home with stunning beach views
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Interior

Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

9.8 out of 10, Exceptional, (197)
"Great codo unit, very close to everything "
The price is CA $252
CA $490 total
includes taxes & fees
Feb 3 - Feb 4
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Oceanfront Condo! Spectacular Views From Private Large Balcony
On the beach

Oceanfront Condo! Spectacular Views From Private Large Balcony

9.0 out of 10, Wonderful, (124)
"Great location! If you are looking for quiet time during the evening hours this isn’t the place for you as The Brunswick restaurant is directly below. If you like music and a great view, it’s an amazing spot! "
The price is CA $143
CA $347 total
includes taxes & fees
Feb 3 - Feb 4
Oceanfront Condo! Spectacular Views From Private Large Balcony
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
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 CA $143
CA $317 total
includes taxes & fees
Feb 4 - Feb 5
Glorious getaway on Portland's Eastern Promenade.
2 duplex
Comfort Duplex, 3 Bedrooms | Private kitchen

2 duplex

3.5 star property
2.0 out of 10, (1)
2 duplex
The Perfect Beach Escape: Cozy 4-Bedroom Retreat
On the beach, sun loungers, beach towels

The Perfect Beach Escape: Cozy 4-Bedroom Retreat

10.0 out of 10, Exceptional, (93)
"Perfect for a family and friends weekend! Lots of room for everyone to be comfortable!"
The Perfect Beach Escape: Cozy 4-Bedroom Retreat
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
Beach House ∆ Prime Location ∆ Steps to the Ocean
3 bedrooms, desk, iron/ironing board, travel crib

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (40)
"Great place.... Very clean and everything you will need to stay. It was three levels and it had supplies needed for the beach (Beach wagon, chairs, towel, sand toys...). We stayed off season so most of the houses were vacant. We would definately come back again. I did send two messages to the owner, but did not get a response. "
The price is CA $214
CA $710 total
includes taxes & fees
Jan 30 - Jan 31
Beach House ∆ Prime Location ∆ Steps to the Ocean
The Globe House on Munjoy Hill - Walk to Breweries
Fridge, microwave, oven, stovetop

The Globe House on Munjoy Hill - Walk to Breweries

10.0 out of 10, Exceptional, (74)
"The Globe House was a wonderful Plato spend a couple of days while exploring Portland. The house itself was immaculate and well appointed, with extra touches that put it a step above: the fresh scent from a diffuser welcomed us, a complimentary bottle of wine awaited us in the refrigerator, and luxe amenities like L’Occitane moisturizer were provided. Great location with easily walkable and excellent restaurants. Our hosts left a fabulous “guide to Portland” for us, with many of their favorite...
The Globe House on Munjoy Hill - Walk to Breweries
Large 2BD cottage 10 min to Pier & Beach Pets ok
Exterior

Large 2BD cottage 10 min to Pier & Beach Pets ok

9.4 out of 10, Exceptional, (26)
"This 2 bedroom cottage was perfect for our 3 day stay.Location was a 10 minute walk to the boardwalk.Would like to come back in the summer."
The price is CA $173
CA $349 total
includes taxes & fees
Mar 1 - Mar 2
Large 2BD cottage 10 min to Pier & Beach Pets ok
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 CA $125
CA $254 total
includes taxes & fees
Jan 30 - Jan 31
Adorable Portland getaway on the 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 CA $287
CA $710 total
includes taxes & fees
Jan 30 - Jan 31
Fall In Love With Portland!
Sensational Beachfront Property Old Orchard Beach, Maine, with indoor elevator
Outdoor dining

Sensational Beachfront Property Old Orchard Beach, Maine, with indoor elevator

9.6 out of 10, Exceptional, (55)
"This house exceeded my expectations and the owner, Jason was wonderful! I rented this beautiful house for my annual Christmas Eve party. It was more than perfect and there was plenty of room for everyone. The pool table was a nice activity for some good family competition. I highly recommend this property and would definitely stay here again. "
Sensational Beachfront Property Old Orchard Beach, Maine, with indoor elevator
East Grand Ave Fabulous Cottage
Beach

East Grand Ave Fabulous Cottage

9.2 out of 10, Wonderful, (131)
"The picture on VRBO leads you to believe you just go down the pathway shown to get to the beach when you are actually in a neighborhood and have to walk down the street to get to the beach. The house was very clean and both beds were very comfortable. The host was very fast to respond to my messages. Needs clean shower liner. We enjoyed our stay. "
East Grand Ave Fabulous Cottage
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Terrace/patio

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

10.0 out of 10, Exceptional, (99)
"This property is stunning, and the view is spectacular. If this were my house, I’d never leave! We had a fabulous time. "
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !
Terrace/patio

Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

10.0 out of 10, Exceptional, (30)
"This property was spectacular! Beautiful views, clean, spacious and comfortable. Great space to share with a larger group. The Host was very responsive. It was an amazing experience even in the winter. "
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !
Charming 110-year former Inn 10' from the Ocean!
Property grounds

Charming 110-year former Inn 10' from the Ocean!

9.8 out of 10, Exceptional, (116)
"Stunning location. Dog friendly beach. Lighthouse in walking distance. "
Charming 110-year former Inn 10' from the Ocean!
Dog-friendly cottage with deck & porch - walk to the beach, pier & town
Beach nearby

Dog-friendly cottage with deck & porch - walk to the beach, pier & town

8.2 out of 10, Very good, (12)
"We enjoyed our brief stay"
Dog-friendly cottage with deck & porch - walk to the beach, pier & town
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.
Don't see what you're looking for?
See all available properties in Great Diamond Island
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Great Diamond Island you may be interested in

Portland Harbor Hotel
Honeymoon Suite, 1 King Bed

Portland Harbor Hotel

4.0 star property
9.2 out of 10, Wonderful, (1451)
"This was our first stay at the Portland Harbor Hotel. The location was in the heart of the old port making it a great starting point for all our adventures. We liked the easy access to parking and all the little perks offered within the hotels. "
The price is CA $176
CA $250 total
includes taxes & fees
Feb 2 - Feb 3
Portland Harbor Hotel
Holiday Inn Portland-By the Bay, an IHG Hotel
Exterior

Holiday Inn Portland-By the Bay, an IHG Hotel

3.0 star property
8.8 out of 10, Excellent, (1132)
"Wonderful, attentive staff. Room was quiet and spacious! Great location! Currently under renovation, but did not impede our stay. Would book again!"
The price is CA $141
CA $156 total
includes taxes & fees
Feb 3 - Feb 4
Holiday Inn Portland-By the Bay, an IHG Hotel
Cambria Hotel Portland Downtown-Old Port
Exterior

Cambria Hotel Portland Downtown-Old Port

3.0 star property
9.2 out of 10, Wonderful, (758)
"I was looking for a place that was easy to get to after flying all day before starting a three day conference. The room was spacious and clean, providing a comfortable bed and a beautiful view. I was able to walk down to old Port board, the ferry, explore restaurants and coffee shops all within minutes from my hotel. "
The price is CA $140
CA $194 total
includes taxes & fees
Feb 5 - Feb 6
Cambria Hotel Portland Downtown-Old Port
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.