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227 rentals
in Portland.
“Henry” Penthouse Suite: Amazing Views, Waterfront, in the heart of the Old Port
140
Condo/Apartment
2 bedrooms
Sleeps 4
3 bathrooms
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Luxury Old Port Penthouse Suite w/Stunning Harbor Views. Parking. Safe + Secure.
172
Condo/Apartment
2 bedrooms
Sleeps 4
2 bathrooms
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Chic One Bedroom Apartment In Portland's Arts District
149
Condo/Apartment
1 bedroom
Sleeps 3
1 bathroom
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“Percival” Penthouse Suite: Breathtaking Views, Cupola, Walk to Restaurants
153
Condo/Apartment
2 bedrooms
Sleeps 4
2 bathrooms
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“Cornelia” Waterfront Penthouse Suite, Prime Old Port Location, Amazing Views!
98
Condo/Apartment
2 bedrooms
Sleeps 4
3 bathrooms
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Historic Condo w/ Casco Bay Views, Fireplace, WiFi & 2 Bikes - Walk Everywhere!
101
Condo/Apartment
1 bedroom
Sleeps 2
1 bathroom
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Charming Peaks Island Cottage
76
Holiday Rental House
1 bedroom
Sleeps 2
1 bathroom
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Glorious getaway on Portland's Eastern Promenade.
76
Condo/Apartment
2 bedrooms
Sleeps 5
1 bathroom
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Spacious 3 Bed in a Prime Old Port Location
135
Condo/Apartment
3 bedrooms
Sleeps 6
1 bathroom
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Historic West End Neighborhood
72
Holiday Rental House
3 bedrooms
Sleeps 5
1 bathroom
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Great Captains House Portland
54
Holiday Rental House
4 bedrooms
Sleeps 12
2 bathrooms
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Bright, spacious home, brand new hot tub, beautiful artwork, gigbit internet
50
Holiday Rental House
3 bedrooms
Sleeps 6
2 bathrooms
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Cozy Getaway In The City
38
Condo/Apartment
1 bedroom
Sleeps 3
1 bathroom
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NEW LISTING ☼ Unique Oceanfront Home. Separate boat rental available.
53
Holiday Rental House
3 bedrooms
Sleeps 4
2 bathrooms
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Hollywood meets seaside charm in the former cottage of famed director, John Ford
33
Holiday Rental House
3 bedrooms
Sleeps 6
2 bathrooms
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Charming, Secluded, Island Getaway!
37
Holiday Rental House
2 bedrooms
Sleeps 6
1 bathroom
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Classic Family Cottage, Ocean View from Porch, Peaceful Rural Location
25
Holiday Rental House
4 bedrooms
Sleeps 8
3 bathrooms
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Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
66
Condo/Apartment
3 bedrooms
Sleeps 10
2 bathrooms
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Classic Island Cottage
43
Holiday Rental House
3 bedrooms
Sleeps 3
1 bathroom
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The 'Water House' Cottage is on a Sandy Beach! Amazing Views!!
32
Holiday Rental House
1 bedroom
Sleeps 3
1 bathroom
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Beautiful House Rental At Diamond Cove At Great Diamond Island
34
Holiday Rental House
3 bedrooms
Sleeps 6
2 bathrooms
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Stunning and Spacious 6 BR Waterfront House with Hot Tub
29
Holiday Rental House
6 bedrooms
Sleeps 14
3 bathrooms
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Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers
24
Condo/Apartment
4 bedrooms
Sleeps 9
2 bathrooms
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Spacious Historic 1st Floor Apartment
35
Condo/Apartment
2 bedrooms
Sleeps 8
1 bathroom
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Art Filled East End Home a short walk to waterfront, restaurants and shops
25
Holiday Rental House
3 bedrooms
Sleeps 3
3 bathrooms
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Walk to Old Port ♦ West End Condo ♦ Parking
41
Condo/Apartment
3 bedrooms
Sleeps 8
1 bathroom
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5 Star Back Cove Hide-Away1 bedroom Back Cove apartment with water views!
18
Holiday Rental House
1 bedroom
Sleeps 2
1 bathroom
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Charming 2-bedroom steps from the Eastern Promenade
46
Condo/Apartment
2 bedrooms
Sleeps 5
1 bathroom
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The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
25
Holiday Rental House
2 bedrooms
Sleeps 6
1 bathroom
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Beautiful Munjoy Hill Private Oasis
39
Condo/Apartment
2 bedrooms
Sleeps 4
1 bathroom
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Perfect Vacation Cottage, Filled with Sunshine and Laughter.
30
Holiday Rental House
3 bedrooms
Sleeps 6
2 bathrooms
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Beautiful getaway on Peaks Island!
22
Holiday Rental House
4 bedrooms
Sleeps 8
3 bathrooms
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Downtown Portland Apartment
45
Condo/Apartment
1 bedroom
Sleeps 3
1 bathroom
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1200 Sq Ft ♦ West End Gem ♦ Perfect Location
65
Condo/Apartment
2 bedrooms
Sleeps 6
1 bathroom
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New Peaks Cottage: Modern amenities, island charm, steps to shore
29
Holiday Rental House
3 bedrooms
Sleeps 8
1 bathroom
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Peaks Island Cottage with beautiful view of Whitehead passage
21
Holiday Rental House
3 bedrooms
Sleeps 6
2 bathrooms
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Spacious 5 Bedroom, 2 Full Baths, Walkable Neighborhood! Close to Breweries!
16
Holiday Rental House
5 bedrooms
Sleeps 16
2 bathrooms
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Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!
20
Holiday Rental House
3 bedrooms
Sleeps 8
3 bathrooms
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Stunning Entire Three Units Apts (USM AREA)
14
Condo/Apartment
9 bedrooms
Sleeps 20
6 bathrooms
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Enjoy Portland With Family or Friends
78
Condo/Apartment
3 bedrooms
Sleeps 8
2 bathrooms
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Vintage Maine & Modern Convenience in Portlands Exclusive East End
21
Condo/Apartment
2 bedrooms
Sleeps 4
1 bathroom
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Adorable Portland getaway on the Eastern Promenade
44
Condo/Apartment
1 bedroom
Sleeps 3
1 bathroom
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2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood
44
Condo/Apartment
2 bedrooms
Sleeps 4
1 bathroom
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Fresh East End Apartment Walkable to Downtown Portland
17
Condo/Apartment
1 bedroom
Sleeps 4
1 bathroom
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Charming Cottage - Great Diamond Island, Waterviews, Path to Beach, Sunset Side
24
Holiday Rental House
3 bedrooms
Sleeps 6
2 bathrooms
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Industrial Farmhouse Chic in Portland's Most Desirable Neighborhood
16
Holiday Rental House
4 bedrooms
Sleeps 9
2 bathrooms
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Waterfront Island Getaway w/two cottages perfect for Multiple or Large Families
15
Holiday Rental House
5 bedrooms
Sleeps 14
3 bathrooms
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Great Ocean View Summer Cottage Rental with Boat Mooring on Great Diamond Island
14
Holiday Rental House
4 bedrooms
Sleeps 8
1 bathroom
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Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch
10
Holiday Rental House
4 bedrooms
Sleeps 8
3 bathrooms
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2 Bedroom Apartment on Top Floor in Portland's West End
17
Condo/Apartment
2 bedrooms
Sleeps 5
1 bathroom
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Frequently Asked Questions about Portland
Do any holiday rentals in Portland have a pool?
Yes, here are some popular holiday rentals in Portland that have a pool:
Classic, cozy family cottage with modern amenities and ocean view from porch
Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch
Updated 2 Bedroom with Roof deck and backyard
See all holiday rentals with a pool in Portland on Tripadvisor
Do any holiday rentals in Portland have internet access?
Yes, here are some popular holiday rentals in Portland that have internet access:
Classic, cozy family cottage with modern amenities and ocean view from porch
Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch
Updated 2 Bedroom with Roof deck and backyard
See all holiday rentals in Portland on Tripadvisor
What are the best pet friendly rentals in Portland?
The best pet friendly rentals in Portland are:
Updated 2 Bedroom with Roof deck and backyard
Casco Bay Sunrise Vista
Stunning White Water Ocean Views From This Peaks Island Home
See all pet friendly holiday rentals in Portland on Tripadvisor
What are some great rentals in Portland that are kid friendly?
Some of the most popular kid friendly rentals in Portland are:
Classic, cozy family cottage with modern amenities and ocean view from porch
Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch
Updated 2 Bedroom with Roof deck and backyard
See all kid friendly holiday rentals in Portland on Tripadvisor