Holiday rentals near Little Diamond Island
We found 617 holiday rentals — enter your dates for availability
If you'd like to stay close to Little Diamond Island, scroll through and discover holiday rentals to find the perfect one for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the amenities that you need and want, which might include parking and a fireplace. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Little Diamond Island
Showing deals for:12 Sept - 19 Sept
Image gallery for Art Filled East End Home a short walk to waterfront, restaurants and shops
9.89.8 out of 10 rating
Exceptional
(28 reviews)
Art Filled East End Home a short walk to waterfront, restaurants and shops
Portland, ME
8% off
Price is NZ$25,563
NZ$25,563
NZ$3,652 per night
includes taxes & fees
Image gallery for Sunny Modern Oasis in Portland’s Trendy East End
1010 out of 10 rating
Exceptional
(48 reviews)
Sunny Modern Oasis in Portland’s Trendy East End
Portland, ME
8% off
Price is NZ$5,012
NZ$5,012
NZ$716 per night
includes taxes & fees
Image gallery for Beautifully built Cape Elizabeth home nestled in the woods on 2.5 acres
1010 out of 10 rating
Exceptional
(15 reviews)
Beautifully built Cape Elizabeth home nestled in the woods on 2.5 acres
Cape Elizabeth, ME
8% off
Price is NZ$12,907
NZ$12,907
NZ$1,844 per night
includes taxes & fees
Image gallery for Elegant, Sunny, 2 Bedroom Townhouse Apartment, in the Heart of Downtown Portland
1010 out of 10 rating
Exceptional
(88 reviews)
Elegant, Sunny, 2 Bedroom Townhouse Apartment, in the Heart of Downtown Portland
Portland, ME
18% off
Price is NZ$4,218
NZ$4,218
NZ$603 per night
includes taxes & fees
Image gallery for Kayak, swim, fish, walk to restaurants, breweries, 19 min to Old Port
1010 out of 10 rating
Exceptional
(8 reviews)
Kayak, swim, fish, walk to restaurants, breweries, 19 min to Old Port
Westbrook, ME
12% off
Price is NZ$12,504
NZ$12,504
NZ$1,786 per night
includes taxes & fees
Image gallery for Oceanfront Cottage with Spectacular Views of Casco Bay
1010 out of 10 rating
Exceptional
(20 reviews)
Oceanfront Cottage with Spectacular Views of Casco Bay
Cape Elizabeth, ME
8% off
Price is NZ$8,224
NZ$8,224
NZ$1,175 per night
includes taxes & fees
Image gallery for Step right out to the beach! Amazing location 7 min to Portland. Unit 4
1010 out of 10 rating
Exceptional
(11 reviews)
Step right out to the beach! Amazing location 7 min to Portland. Unit 4
South Portland, ME
8% off
Price is NZ$8,333
NZ$8,333
NZ$1,190 per night
includes taxes & fees
Image gallery for Beautiful NEW apt on top of Munjoy Hill with private deck and private parking.
1010 out of 10 rating
Exceptional
(13 reviews)
Beautiful NEW apt on top of Munjoy Hill with private deck and private parking.
Portland, ME
8% off
Price is NZ$4,751
NZ$4,751
NZ$679 per night
includes taxes & fees
Image gallery for Entire House - three suites - conferences, reunions, retreats
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Entire House - three suites - conferences, reunions, retreats
Westbrook, ME
8% off
Price is NZ$14,449
NZ$14,449
NZ$2,064 per night
includes taxes & fees
Image gallery for Romantic apt:West End +parking
1010 out of 10 rating
Exceptional
(6 reviews)
Romantic apt:West End +parking
Portland, ME
12% off
Price is NZ$6,722
NZ$6,722
NZ$960 per night
includes taxes & fees
Image gallery for Spacious and bright, 1st floor apartment in Historical Yarmouth Village
1010 out of 10 rating
Exceptional
(19 reviews)
Spacious and bright, 1st floor apartment in Historical Yarmouth Village
Yarmouth, ME
17% off
Price is NZ$3,211
NZ$3,211
NZ$459 per night
includes taxes & fees
Image gallery for Willard Beach Neighborhood-Close to all Southern Maine has to offer!
9.89.8 out of 10 rating
Exceptional
(66 reviews)
Willard Beach Neighborhood-Close to all Southern Maine has to offer!
South Portland, ME
8% off
Price is NZ$5,182
NZ$5,182
NZ$740 per night
includes taxes & fees
Image gallery for Wonderful Portland Waterfront Home
9.69.6 out of 10 rating
Exceptional
(27 reviews)
Wonderful Portland Waterfront Home
Portland, ME
8% off
Price is NZ$8,474
NZ$8,474
NZ$1,211 per night
includes taxes & fees
Image gallery for Back yard paradise
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Back yard paradise
Portland, ME
8% off
Price is NZ$7,602
NZ$7,602
NZ$1,086 per night
includes taxes & fees
Image gallery for “The Beach House” Peaks Island Oceanfront Cottage
9.89.8 out of 10 rating
Exceptional
(40 reviews)
“The Beach House” Peaks Island Oceanfront Cottage
Peaks Island, ME
8% off
Price is NZ$13,208
NZ$13,208
NZ$1,887 per night
includes taxes & fees
Image gallery for Newly Renovated Apartment in Willard Square Area of South Portland, Maine.
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Newly Renovated Apartment in Willard Square Area of South Portland, Maine.
South Portland, ME
16% off
Price is NZ$3,026
NZ$3,026
NZ$432 per night
includes taxes & fees
Image gallery for So. Po. Sweet Spot
9.69.6 out of 10 rating
Exceptional
(5 reviews)
So. Po. Sweet Spot
South Portland, ME
8% off
Price is NZ$3,261
NZ$3,261
NZ$466 per night
includes taxes & fees
Image gallery for Harborview - Curated East End Escape w/ Parking
1010 out of 10 rating
Exceptional
(5 reviews)
Harborview - Curated East End Escape w/ Parking
Portland, ME
8% off
Price is NZ$8,713
NZ$8,713
NZ$1,245 per night
includes taxes & fees
Image gallery for Charming Great Diamond Island Cottage w/Waterviews - Bus. Lic.# STHR-003849-2021
1010 out of 10 rating
Exceptional
(25 reviews)
Charming Great Diamond Island Cottage w/Waterviews - Bus. Lic.# STHR-003849-2021
Portland, ME
8% off
Price is NZ$6,869
NZ$6,869
NZ$981 per night
includes taxes & fees
Image gallery for Cozy 3BR - Pet Friendly - Near Portland - Parking
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Cozy 3BR - Pet Friendly - Near Portland - Parking
Westbrook, ME
8% off
Price is NZ$4,631
NZ$4,631
NZ$662 per night
includes taxes & fees
Image gallery for Best Ocean View In Portland!
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Best Ocean View In Portland!
Portland, ME
8% off
Price is NZ$7,887
NZ$7,887
NZ$1,127 per night
includes taxes & fees
Image gallery for Garden Gem ★ 5 Min to Old Port ★ Spacious + New
9.49.4 out of 10 rating
Exceptional
(16 reviews)
Garden Gem ★ 5 Min to Old Port ★ Spacious + New
Portland, ME
8% off
Price is NZ$4,999
NZ$4,999
NZ$714 per night
includes taxes & fees
Image gallery for The best place for the money!!!
8.88.8 out of 10 rating
Excellent
(21 reviews)
The best place for the money!!!
Portland, ME
8% off
Price is NZ$10,250
NZ$10,250
NZ$1,464 per night
includes taxes & fees
Image gallery for Brand new single family Munjoy Hill
1010 out of 10 rating
Exceptional
(13 reviews)
Brand new single family Munjoy Hill
Portland, ME
8% off
Price is NZ$5,158
NZ$5,158
NZ$737 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Little Diamond Island
Showing deals for: 12 Sept - 15 Sept
Cottage in the Woods on Picturesque Island
Sleeps 5 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
The current price is NZ$1,187
NZ$1,187
for 3 nights, 1 cabin
NZ$396 per night
includes taxes & fees
3-bedroom island Retreat on Peaks Island
Sleeps 6 · 3 bedrooms · 2 bathrooms
The current price is NZ$2,696
NZ$2,696
for 3 nights, 1 home
NZ$899 per night
includes taxes & fees
New Ocean-front, Peaks Island, Portland home, Beaches,
Sleeps 6 · 2 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
The current price is NZ$5,682
NZ$5,682
for 3 nights, 1 home
NZ$1,894 per night
includes taxes & fees
3 bedroom home right of way to private beach, with deck and enclosed porch
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
The current price is NZ$2,053
NZ$2,053
for 3 nights, 1 home
NZ$684 per night
includes taxes & fees
Oceanfront Boathouse on Casco Bay
Sleeps 5 · 2 bedrooms · 1 bathroom
The current price is NZ$9,643
NZ$9,643
for 3 nights, 1 home
NZ$3,214 per night
includes taxes & fees
NEW 1 BDR-Heart of Munjoy Hill
Sleeps 4 · 1 bedroom · 1 bathroom
The current price is NZ$2,473
NZ$2,473
for 3 nights, 1 apartment
NZ$824 per night
includes taxes & fees
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
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