A calm sea with a sailboat and rocky coastline.

Great Diamond Island Vacation Rentals

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Our top choices for Great Diamond Island vacation rentals

Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is CA $307
CA $334 total
includes taxes & fees
Jul 21 - Jul 22
Fortland Island Campground

Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland

Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland
Pine Point
9.6 out of 10, Exceptional, (45 reviews)
"Beautiful, clean place to stay and dogs welcome "
United States
Anonymous traveller
The price is CA $204
CA $513 total
includes taxes & fees
Jul 22 - Jul 23
Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland

Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very good, (10 reviews)
"Check in process was smooth and description of area was accurate though cleanliness of unit left a lot to be desired. There was a lot of hair all over the apartment floor and bedding when we arrived with old stains in bedding. Booked 2 nights and ended up getting a hotel for the 2nd day."
United States
Raul
The price is CA $162
CA $267 total
includes taxes & fees
Jul 22 - Jul 23
Studio Apartment near downtown Walkable!

Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach

Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach
Grand Beach
9.8 out of 10, Exceptional, (47 reviews)
"Stay was good. It was clean well decorated and equipped with everything you need"
United States
Tom K.
The price is CA $168
CA $416 total
includes taxes & fees
Jul 28 - Jul 29
Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach

City Oasis and Spa/Close to Beaches

City Oasis and Spa/Close to Beaches
Downtown Saco
10.0 out of 10, Exceptional, (1 review)
"Clean room very nice."
United States
scot r.
The price is CA $225
CA $499 total
includes taxes & fees
Jul 20 - Jul 21
City Oasis and Spa/Close to Beaches

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (37 reviews)
"Absolutely wonderful little place to stay in Scarborough! "
United States
Eric S.
The price is CA $294
CA $507 total
includes taxes & fees
Aug 9 - Aug 10
Pine Point Beach private, quaint, charming studio.

Cozy Coastal 2-bedroom condo with AC, WiFi in welcoming Saco

Cozy Coastal 2-bedroom condo with AC, WiFi in welcoming Saco
Saco
9.8 out of 10, Exceptional, (6 reviews)
"The coastal condo was comfortable and a great place to stay! "
United States
Tara P.
The price is CA $284
CA $608 total
includes taxes & fees
Jul 20 - Jul 21
Cozy Coastal 2-bedroom condo with AC, WiFi in welcoming Saco

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (30 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is CA $291
CA $471 total
includes taxes & fees
Jul 20 - Jul 21
Sunny Spot with Private Parking.

Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.6 out of 10, Exceptional, (7 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is CA $258
CA $443 total
includes taxes & fees
Aug 3 - Aug 4
Mid Coast Getaway w/ water views

Sunny Cottage

Sunny Cottage
Biddeford
10.0 out of 10, Exceptional, (57 reviews)
"Exactly as described, close to everything."
United States
Erika J.
The price is CA $284
CA $511 total
includes taxes & fees
Jul 30 - Jul 31
Sunny Cottage

Cozy 3BR | Pet Friendly | Near Portland | Parking

Cozy 3BR | Pet Friendly | Near Portland | Parking
Westbrook
10.0 out of 10, Exceptional, (13 reviews)
"We had a great stay here. It was very clean and conveniently located."
United States
Angela B.
The price is CA $370
CA $769 total
includes taxes & fees
Aug 9 - Aug 10
Cozy 3BR | Pet Friendly | Near Portland | Parking

New Listing! AmongstTheAspens - Off-Grid Tiny Home

New Listing! AmongstTheAspens - Off-Grid Tiny Home
Saco
9.2 out of 10, Wonderful, (17 reviews)
"Had a great stay, very private property. House was very clean and user friendly. Would definitely stay again, thanks"
United States
Doug C.
The price is CA $390
CA $487 total
includes taxes & fees
Jul 22 - Jul 23
New Listing! AmongstTheAspens - Off-Grid Tiny Home

The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!

The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!
Downtown Saco
10.0 out of 10, Exceptional, (25 reviews)
"Great space, responsive host, great location!"
United States
Reed C.
The price is CA $209
CA $479 total
includes taxes & fees
Jul 22 - Jul 23
The Saco Suite - Downtown, Dog Friendly, Sleeps 4, Walk to Bars & Restaurants!

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (10 reviews)
"Apartment was very cute, clean, and just what I was looking for. Jennifer was very accommodating and understanding "
United States
Jolee S.
The price is CA $390
CA $617 total
includes taxes & fees
Jul 21 - Jul 22
Peaceful & minutes from the Old Port with private parking

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (38 reviews)
"Overall a pleasing stay."
United States
Mallory D.
The price is CA $196
CA $649 total
includes taxes & fees
Jul 22 - Jul 23
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Welcome to our BoHo Treehouse!

Welcome to our BoHo Treehouse!
Downtown Saco
9.8 out of 10, Exceptional, (10 reviews)
"We enjoyed our stay in Saco! The apartment was adorable and had all the necessities! "
United States
Sandy B.
The price is CA $248
CA $484 total
includes taxes & fees
Jul 21 - Jul 22
Welcome to our BoHo Treehouse!

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (54 reviews)
"Wonderful stay!"
United States
Erika T.
The price is CA $284
CA $520 total
includes taxes & fees
Jul 21 - Jul 22
Full sized home

Charming Rustic Cottage

Charming Rustic Cottage
Old Orchard Beach
The price is CA $219
CA $270 total
includes taxes & fees
Jul 26 - Jul 27
Charming Rustic Cottage

Modern dome w/ full bath + spa access - 04

Modern dome w/ full bath + spa access - 04
Freeport
10.0 out of 10, Exceptional, (4 reviews)
"Pet friendly and the experience is just amazing. Thank you for having us! "
United States
Rene B.
The price is CA $415
CA $662 total
includes taxes & fees
Jul 23 - Jul 24
Modern dome w/ full bath + spa access - 04

Elegant condo - walk to Portland's best restaurants & Old Port

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.4 out of 10, Exceptional, (81 reviews)
"Lovely unit. Very comfortable bed. Nice to have off street parking. Walkable to Old Port. Would def stay again. "
United States
Erin H.
The price is CA $236
CA $719 total
includes taxes & fees
Jul 22 - Jul 23
Elegant condo - walk to Portland's best restaurants & 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.
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Top Great Diamond Island Hotel Reviews

Find out more about Great Diamond Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Great Diamond Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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