Holiday Rentals in Portland
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Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 km
332 rentals in Portland.
“Henry” Penthouse Suite: Amazing Views, Waterfront, in the heart of the Old Port
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Chic One Bedroom Apartment In Portland's Arts District
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Luxury Old Port Penthouse Suite w/Stunning Harbor Views. Parking. Safe + Secure.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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“Percival” Penthouse Suite: Breathtaking Views, Cupola, Walk to Restaurants
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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“Cornelia” Waterfront Penthouse Suite, Prime Old Port Location, Amazing Views!
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Historic Condo w/ Casco Bay Views, Fireplace, WiFi & 2 Bikes - Walk Everywhere!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Glorious getaway on Portland's Eastern Promenade.
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Charming Peaks Island Cottage
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Historic West End Neighborhood
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Chic 3 BR Retreat- Prime Old Port Spot with parking- Park and walk the town
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Great Captains House Portland
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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NEW LISTING ☼ Unique Oceanfront Home. Separate boat rental available.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Bright, spacious home, brand new hot tub, beautiful artwork, gigbit internet
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Hollywood meets seaside charm in the former cottage of famed director, John Ford
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming, Secluded, Island Getaway!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy Getaway In The City
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Stunning and Spacious 6 BR Waterfront House with Hot Tub
Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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The 'Water House' Cottage is on a Sandy Beach! Amazing Views!!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Spacious Historic 1st Floor Apartment
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Classic Family Cottage, Ocean View from Porch, Peaceful Rural Location
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Walk to Old Port ♦ West End Condo ♦ Parking
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Classic Island Cottage
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful House Rental At Diamond Cove At Great Diamond Island
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Art Filled East End Home a short walk to waterfront, restaurants and shops
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming 2-bedroom steps from the Eastern Promenade
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Adorable Portland getaway on the Eastern Promenade
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Charming Cottage - Great Diamond Island, Waterviews, Path to Beach, Sunset Side
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Perfect Vacation Cottage, Filled with Sunshine and Laughter.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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5 Star Back Cove Hide-Away1 bedroom Back Cove apartment with water views!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Adorable Peaks Island Cottage
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful getaway on Peaks Island!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Enjoy Portland With Family or Friends
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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New Peaks Cottage: Modern amenities, island charm, steps to shore
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Peaks Island Cottage with beautiful view of Whitehead passage
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Entire Three Units Apts (USM AREA)
Condo/Apartment
9 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
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Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Downtown Portland Apartment
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Elegant condo - walk to Portland's best restaurants & Old Port
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Vintage Maine & Modern Convenience in Portlands Exclusive East End
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Industrial Farmhouse Chic in Portland's Most Desirable Neighborhood
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Evergreen cottage 5' from the water
Holiday Rental House
5 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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1200 Sq Ft ♦ West End Gem ♦ Perfect Location
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Munjoy Hill Private Oasis
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Classic turn of the century Maine cottage - Price Reduction 8/20 to 9/10!
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Great Ocean View Summer Cottage Rental with Boat Mooring on Great Diamond Island
Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Panoramic Water, Island & City Views w/Private Roof Deck
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Showing results 1-50 of 332
Frequently Asked Questions about Portland
- 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
- 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
- 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