Portland holiday homes
We found 2,299 holiday rentals — enter your dates for availability
Discover a selection of private holiday rentals close to Portland, ME (PWM-Portland Intl. Jetport) that provide the perfect home base for your trip. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for hanging out with the people that matter most, which might include a fireplace and a washer and dryer. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Portland, ME (PWM-Portland Intl. Jetport)
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 Ocean Views! Walk to the Beach!
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Ocean Views! Walk to the Beach!
Old Orchard Beach, ME
8% off
Price is NZ$10,694
NZ$10,694
NZ$1,528 per night
includes taxes & fees
Image gallery for Ocean view! Cozy Condo w/ Kitchen, Living Area, Porch, 2 Reserved Parking Spaces
1010 out of 10 rating
Exceptional
(12 reviews)
Ocean view! Cozy Condo w/ Kitchen, Living Area, Porch, 2 Reserved Parking Spaces
Old Orchard Beach, ME
8% off
Price is NZ$2,518
NZ$2,518
NZ$360 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 Africa-Inspired Downstairs Master "Suite" Experience on the Coast of Maine
1010 out of 10 rating
Exceptional
(7 reviews)
Africa-Inspired Downstairs Master "Suite" Experience on the Coast of Maine
Kennebunkport, ME
8% off
Price is NZ$14,950
NZ$14,950
NZ$2,136 per night
includes taxes & fees
Image gallery for Beautiful farmhouse with hiking trails/kayaking. 5 minutes to town or ocean!
1010 out of 10 rating
Exceptional
(6 reviews)
Beautiful farmhouse with hiking trails/kayaking. 5 minutes to town or ocean!
Freeport, ME
8% off
Price is NZ$10,154
NZ$10,154
NZ$1,451 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 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 Updated cottage, walk to beach, screened in porch
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Updated cottage, walk to beach, screened in porch
Old Orchard Beach, ME
8% off
Price is NZ$4,418
NZ$4,418
NZ$631 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 Highland Lake House
9.89.8 out of 10 rating
Exceptional
(28 reviews)
Highland Lake House
Windham, ME
8% off
Price is NZ$6,612
NZ$6,612
NZ$945 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 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 Spacious Family Home, minutes to beaches and hiking trails! sleeps 9
1010 out of 10 rating
Exceptional
(15 reviews)
Spacious Family Home, minutes to beaches and hiking trails! sleeps 9
Scarborough, ME
12% off
Price is NZ$8,797
NZ$8,797
NZ$1,257 per night
includes taxes & fees
Image gallery for Spacious & sunny, 7 minutes from the beach!
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Spacious & sunny, 7 minutes from the beach!
Old Orchard Beach, ME
8% off
Price is NZ$6,688
NZ$6,688
NZ$955 per night
includes taxes & fees
Image gallery for Relax in Raymond's lakefront 2-bedroom vacation home, just steps to Sebago Lake
1010 out of 10 rating
Exceptional
(5 reviews)
Relax in Raymond's lakefront 2-bedroom vacation home, just steps to Sebago Lake
Raymond, ME
8% off
Price is NZ$5,072
NZ$5,072
NZ$725 per night
includes taxes & fees
Image gallery for Bay-View. Waterfront Log cabin on the bay. Pet Friendly.
9.89.8 out of 10 rating
Exceptional
(26 reviews)
Bay-View. Waterfront Log cabin on the bay. Pet Friendly.
Harpswell, ME
8% off
Price is NZ$5,355
NZ$5,355
NZ$765 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 Grace's Place, a Real Maine Cottage
9.89.8 out of 10 rating
Exceptional
(42 reviews)
Grace's Place, a Real Maine Cottage
Harpswell, ME
9% off
Price is NZ$3,441
NZ$3,441
NZ$492 per night
includes taxes & fees
Image gallery for Cozy Sebago Lake Retreat
1010 out of 10 rating
Exceptional
(23 reviews)
Cozy Sebago Lake Retreat
Raymond, ME
8% off
Price is NZ$6,079
NZ$6,079
NZ$868 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 Beachy retreat!
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Beachy retreat!
Old Orchard Beach, ME
8% off
Price is NZ$2,751
NZ$2,751
NZ$393 per night
includes taxes & fees
Find spaces that suit your style
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Cottage
Villa
Chalet
Find the best place to stay - Portland
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
215 reviews(215 reviews)
Orchid Harbor, Bailey Island 3BR
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Lakefront Cottage with New HOT TUB. . Located 20 minutes from Portland
Sleeps 6 · 2 bedrooms · 1 bathroom
8.88.8 out of 10
Excellentexcellent
39 reviews(39 reviews)
The Weldon Hotel
Sleeps 2 · 1 bedroom
9.89.8 out of 10
Exceptionalexceptional
62 reviews(62 reviews)
Cozy and Quiet beautiful home 1 Bedroom private bathroom Portland with WiFi, AC
Sleeps 4 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
Beautifully Spacious with Charm
Sleeps 4 · 2 bedrooms · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
71 reviews(71 reviews)
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
More for lessMore space, more privacy, more amenities — more value