We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in Portland

Revenue impacts this sort order. Learn more

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, holiday rental in Portland
“Henry” Penthouse Suite: Amazing Views, Waterfront, in the heart of the Old Port, holiday rental in Portland
“Henry” Penthouse Suite: Amazing Views, Waterfront, in the heart of the Old Port, holiday rental 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
More info
Check-in
Check-out
Chic One Bedroom Apartment In Portland's Arts District, holiday rental in Portland
Chic One Bedroom Apartment In Portland's Arts District, holiday rental in Portland
Chic One Bedroom Apartment In Portland's Arts District, holiday rental in Portland

Chic One Bedroom Apartment In Portland's Arts District

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
Luxury Old Port Penthouse Suite w/Stunning Harbor Views. Parking. Safe + Secure., holiday rental in Portland
Luxury Old Port Penthouse Suite w/Stunning Harbor Views. Parking. Safe + Secure., holiday rental in Portland
Luxury Old Port Penthouse Suite w/Stunning Harbor Views. Parking. Safe + Secure., holiday rental in Portland

Luxury Old Port Penthouse Suite w/Stunning Harbor Views. Parking. Safe + Secure.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
“Percival” Penthouse Suite: Breathtaking Views, Cupola, Walk to Restaurants, holiday rental in Portland
“Percival” Penthouse Suite: Breathtaking Views, Cupola, Walk to Restaurants, holiday rental in Portland
“Percival” Penthouse Suite: Breathtaking Views, Cupola, Walk to Restaurants, holiday rental in Portland

“Percival” Penthouse Suite: Breathtaking Views, Cupola, Walk to Restaurants

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
“Cornelia” Waterfront Penthouse Suite, Prime Old Port Location, Amazing Views!, holiday rental in Portland
“Cornelia” Waterfront Penthouse Suite, Prime Old Port Location, Amazing Views!, holiday rental in Portland
“Cornelia” Waterfront Penthouse Suite, Prime Old Port Location, Amazing Views!, holiday rental in Portland

“Cornelia” Waterfront Penthouse Suite, Prime Old Port Location, Amazing Views!

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Historic Condo w/ Casco Bay Views, Fireplace, WiFi & 2 Bikes - Walk Everywhere!, holiday rental in Portland
Historic Condo w/ Casco Bay Views, Fireplace, WiFi & 2 Bikes - Walk Everywhere!, holiday rental in Portland
Historic Condo w/ Casco Bay Views, Fireplace, WiFi & 2 Bikes - Walk Everywhere!, holiday rental in Portland

Historic Condo w/ Casco Bay Views, Fireplace, WiFi & 2 Bikes - Walk Everywhere!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Glorious getaway on Portland's Eastern Promenade., holiday rental in Portland
Glorious getaway on Portland's Eastern Promenade., holiday rental in Portland
Glorious getaway on Portland's Eastern Promenade., holiday rental in Portland

Glorious getaway on Portland's Eastern Promenade.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Charming Peaks Island Cottage, holiday rental in Portland
Charming Peaks Island Cottage, holiday rental in Portland
Charming Peaks Island Cottage, holiday rental in Portland

Charming Peaks Island Cottage

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Historic West End Neighborhood, holiday rental in Portland
Historic West End Neighborhood, holiday rental in Portland
Historic West End Neighborhood, holiday rental in Portland

Historic West End Neighborhood

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Chic 3 BR Retreat- Prime Old Port Spot with parking- Park and walk the town, holiday rental in Portland
Chic 3 BR Retreat- Prime Old Port Spot with parking- Park and walk the town, holiday rental in Portland
Chic 3 BR Retreat- Prime Old Port Spot with parking- Park and walk the town, holiday rental in Portland

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
More info
Check-in
Check-out
Great Captains House Portland, holiday rental in Portland
Great Captains House Portland, holiday rental in Portland
Great Captains House Portland, holiday rental in Portland

Great Captains House Portland

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
NEW LISTING ☼ Unique Oceanfront Home. Separate boat rental available., holiday rental in Portland
NEW LISTING ☼ Unique Oceanfront Home. Separate boat rental available., holiday rental in Portland
NEW LISTING ☼ Unique Oceanfront Home. Separate boat rental available., holiday rental in Portland

NEW LISTING ☼ Unique Oceanfront Home. Separate boat rental available.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants, holiday rental in Portland
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants, holiday rental in Portland
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants, holiday rental in Portland

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Bright, spacious home, brand new hot tub, beautiful artwork, gigbit internet, holiday rental in Portland
Bright, spacious home, brand new hot tub, beautiful artwork, gigbit internet, holiday rental in Portland
Bright, spacious home, brand new hot tub, beautiful artwork, gigbit internet, holiday rental in Portland

Bright, spacious home, brand new hot tub, beautiful artwork, gigbit internet

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Hollywood meets seaside charm in the former cottage of famed director, John Ford, holiday rental in Portland
Hollywood meets seaside charm in the former cottage of famed director, John Ford, holiday rental in Portland
Hollywood meets seaside charm in the former cottage of famed director, John Ford, holiday rental in Portland

Hollywood meets seaside charm in the former cottage of famed director, John Ford

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Charming, Secluded, Island Getaway!, holiday rental in Portland
Charming, Secluded, Island Getaway!, holiday rental in Portland
Charming, Secluded, Island Getaway!, holiday rental in Portland

Charming, Secluded, Island Getaway!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Cozy Getaway In The City, holiday rental in Portland
Cozy Getaway In The City, holiday rental in Portland
Cozy Getaway In The City, holiday rental in Portland

Cozy Getaway In The City

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
Stunning and Spacious 6 BR Waterfront House with Hot Tub, holiday rental in Portland
Stunning and Spacious 6 BR Waterfront House with Hot Tub, holiday rental in Portland
Stunning and Spacious 6 BR Waterfront House with Hot Tub, holiday rental in Portland

Stunning and Spacious 6 BR Waterfront House with Hot Tub

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
The 'Water House' Cottage is on a Sandy Beach! Amazing Views!!, holiday rental in Portland
The 'Water House' Cottage is on a Sandy Beach! Amazing Views!!, holiday rental in Portland
The 'Water House' Cottage is on a Sandy Beach! Amazing Views!!, holiday rental in Portland

The 'Water House' Cottage is on a Sandy Beach! Amazing Views!!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
Spacious Historic 1st Floor Apartment, holiday rental in Portland
Spacious Historic 1st Floor Apartment, holiday rental in Portland
Spacious Historic 1st Floor Apartment, holiday rental in Portland

Spacious Historic 1st Floor Apartment

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Classic Family Cottage, Ocean View from Porch, Peaceful Rural Location, holiday rental in Portland
Classic Family Cottage, Ocean View from Porch, Peaceful Rural Location, holiday rental in Portland
Classic Family Cottage, Ocean View from Porch, Peaceful Rural Location, holiday rental in Portland

Classic Family Cottage, Ocean View from Porch, Peaceful Rural Location

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Walk to Old Port ♦ West End Condo ♦ Parking, holiday rental in Portland
Walk to Old Port ♦ West End Condo ♦ Parking, holiday rental in Portland
Walk to Old Port ♦ West End Condo ♦ Parking, holiday rental in Portland

Walk to Old Port ♦ West End Condo ♦ Parking

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Classic Island Cottage, holiday rental in Portland
Classic Island Cottage, holiday rental in Portland
Classic Island Cottage, holiday rental in Portland

Classic Island Cottage

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Beautiful House Rental At Diamond Cove At Great Diamond Island, holiday rental in Portland
Beautiful House Rental At Diamond Cove At Great Diamond Island, holiday rental in Portland
Beautiful House Rental At Diamond Cove At Great Diamond Island, holiday rental in Portland

Beautiful House Rental At Diamond Cove At Great Diamond Island

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries, holiday rental in Portland
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries, holiday rental in Portland
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries, holiday rental in Portland

The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Art Filled East End Home a short walk to waterfront, restaurants and shops, holiday rental in Portland
Art Filled East End Home a short walk to waterfront, restaurants and shops, holiday rental in Portland
Art Filled East End Home a short walk to waterfront, restaurants and shops, holiday rental in Portland

Art Filled East End Home a short walk to waterfront, restaurants and shops

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Charming 2-bedroom steps from the Eastern Promenade, holiday rental in Portland
Charming 2-bedroom steps from the Eastern Promenade, holiday rental in Portland
Charming 2-bedroom steps from the Eastern Promenade, holiday rental in Portland

Charming 2-bedroom steps from the Eastern Promenade

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Adorable Portland getaway on the Eastern Promenade, holiday rental in Portland
Adorable Portland getaway on the Eastern Promenade, holiday rental in Portland
Adorable Portland getaway on the Eastern Promenade, holiday rental in Portland

Adorable Portland getaway on the Eastern Promenade

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
Charming Cottage - Great Diamond Island, Waterviews, Path to Beach, Sunset Side, holiday rental in Portland
Charming Cottage - Great Diamond Island, Waterviews, Path to Beach, Sunset Side, holiday rental in Portland
Charming Cottage - Great Diamond Island, Waterviews, Path to Beach, Sunset Side, holiday rental in Portland

Charming Cottage - Great Diamond Island, Waterviews, Path to Beach, Sunset Side

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Perfect Vacation Cottage, Filled with Sunshine and Laughter., holiday rental in Portland
Perfect Vacation Cottage, Filled with Sunshine and Laughter., holiday rental in Portland
Perfect Vacation Cottage, Filled with Sunshine and Laughter., holiday rental in Portland

Perfect Vacation Cottage, Filled with Sunshine and Laughter.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
5 Star Back Cove Hide-Away1 bedroom Back Cove apartment with water views!, holiday rental in Portland
5 Star Back Cove Hide-Away1 bedroom Back Cove apartment with water views!, holiday rental in Portland
5 Star Back Cove Hide-Away1 bedroom Back Cove apartment with water views!, holiday rental in Portland

5 Star Back Cove Hide-Away1 bedroom Back Cove apartment with water views!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Adorable Peaks Island Cottage, holiday rental in Portland
Adorable Peaks Island Cottage, holiday rental in Portland
Adorable Peaks Island Cottage, holiday rental in Portland

Adorable Peaks Island Cottage

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Beautiful getaway on Peaks Island!, holiday rental in Portland
Beautiful getaway on Peaks Island!, holiday rental in Portland
Beautiful getaway on Peaks Island!, holiday rental in Portland

Beautiful getaway on Peaks Island!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Enjoy Portland With Family or Friends, holiday rental in Portland
Enjoy Portland With Family or Friends, holiday rental in Portland
Enjoy Portland With Family or Friends, holiday rental in Portland

Enjoy Portland With Family or Friends

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
New Peaks Cottage: Modern amenities, island charm, steps to shore, holiday rental in Portland
New Peaks Cottage: Modern amenities, island charm, steps to shore, holiday rental in Portland
New Peaks Cottage: Modern amenities, island charm, steps to shore, holiday rental in Portland

New Peaks Cottage: Modern amenities, island charm, steps to shore

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Peaks Island Cottage with beautiful view of Whitehead passage, holiday rental in Portland
Peaks Island Cottage with beautiful view of Whitehead passage, holiday rental in Portland
Peaks Island Cottage with beautiful view of Whitehead passage, holiday rental in Portland

Peaks Island Cottage with beautiful view of Whitehead passage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Stunning Entire Three Units Apts  (USM AREA), holiday rental in Portland
Stunning Entire Three Units Apts  (USM AREA), holiday rental in Portland
Stunning Entire Three Units Apts  (USM AREA), holiday rental in Portland

Stunning Entire Three Units Apts (USM AREA)

Condo/Apartment
9 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
More info
Check-in
Check-out
Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!, holiday rental in Portland
Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!, holiday rental in Portland
Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!, holiday rental in Portland

Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Downtown Portland Apartment, holiday rental in Portland
Downtown Portland Apartment, holiday rental in Portland
Downtown Portland Apartment, holiday rental in Portland

Downtown Portland Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
Elegant condo - walk to Portland's best restaurants & Old Port, holiday rental in Portland
Elegant condo - walk to Portland's best restaurants & Old Port, holiday rental in Portland
Elegant condo - walk to Portland's best restaurants & Old Port, holiday rental in Portland

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Vintage Maine & Modern Convenience in Portlands Exclusive East End, holiday rental in Portland
Vintage Maine & Modern Convenience in Portlands Exclusive East End, holiday rental in Portland
Vintage Maine & Modern Convenience in Portlands Exclusive East End, holiday rental in Portland

Vintage Maine & Modern Convenience in Portlands Exclusive East End

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood, holiday rental in Portland
2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood, holiday rental in Portland
2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood, holiday rental in Portland

2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Industrial Farmhouse Chic in Portland's Most Desirable Neighborhood, holiday rental in Portland
Industrial Farmhouse Chic in Portland's Most Desirable Neighborhood, holiday rental in Portland
Industrial Farmhouse Chic in Portland's Most Desirable Neighborhood, holiday rental in Portland

Industrial Farmhouse Chic in Portland's Most Desirable Neighborhood

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
Evergreen cottage 5' from the water, holiday rental in Portland
Evergreen cottage 5' from the water, holiday rental in Portland
Evergreen cottage 5' from the water, holiday rental in Portland

Evergreen cottage 5' from the water

Holiday Rental House
5 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
1200 Sq Ft ♦ West End Gem ♦ Perfect Location, holiday rental in Portland
1200 Sq Ft ♦ West End Gem ♦ Perfect Location, holiday rental in Portland
1200 Sq Ft ♦ West End Gem ♦ Perfect Location, holiday rental in Portland

1200 Sq Ft ♦ West End Gem ♦ Perfect Location

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Beautiful Munjoy Hill Private Oasis, holiday rental in Portland
Beautiful Munjoy Hill Private Oasis, holiday rental in Portland
Beautiful Munjoy Hill Private Oasis, holiday rental in Portland

Beautiful Munjoy Hill Private Oasis

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Classic turn of the century Maine cottage - Price Reduction 8/20 to 9/10!, holiday rental in Portland
Classic turn of the century Maine cottage - Price Reduction 8/20 to 9/10!, holiday rental in Portland
Classic turn of the century Maine cottage - Price Reduction 8/20 to 9/10!, holiday rental in Portland

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
More info
Check-in
Check-out
Great Ocean View Summer Cottage Rental with Boat Mooring on Great Diamond Island, holiday rental in Portland
Great Ocean View Summer Cottage Rental with Boat Mooring on Great Diamond Island, holiday rental in Portland
Great Ocean View Summer Cottage Rental with Boat Mooring on Great Diamond Island, holiday rental in Portland

Great Ocean View Summer Cottage Rental with Boat Mooring on Great Diamond Island

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch, holiday rental in Portland
Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch, holiday rental in Portland
Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch, holiday rental in Portland

Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Panoramic Water, Island & City Views w/Private Roof Deck, holiday rental in Portland
Panoramic Water, Island & City Views w/Private Roof Deck, holiday rental in Portland
Panoramic Water, Island & City Views w/Private Roof Deck, holiday rental in Portland

Panoramic Water, Island & City Views w/Private Roof Deck

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Showing results 1-50 of 332
Frequently Asked Questions about Portland