
Holiday houses in Portland
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Top-rated holiday rentals in Portland
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Portland holiday rentals
Other great holiday rentals in Portland
Top Guest favourite

Apartment in East End
4.98 out of 5 average rating, 95 reviewsHarborview - Curated East End Escape w/ Parking
Top Guest favourite

Cabin in Freeport
5 out of 5 average rating, 55 reviewsThe Maine Frame: Cozy Firepit 7 Mins to L.L. Bean
Superhost

Hotel room in Downtown Portland
4.87 out of 5 average rating, 488 reviewsEateries, nightlife, galleries – walk to it all
Top Guest favourite

Apartment in Cape Elizabeth
4.99 out of 5 average rating, 81 reviewsCrescent Beach Gardens

Apartment in Downtown Portland
5 out of 5 average rating, 3 reviewsCaptain Axel's Sophisticated Ocean View Getaway!
Guest favourite

Private room in Portland
4.88 out of 5 average rating, 744 reviewsClose to EVERYthing Portland + great neighborhood
Guest favourite

Private room in South Portland
4.89 out of 5 average rating, 377 reviewsAiry Room in Antique Victorian - SOPO
Top Guest favourite

Home in Cape Elizabeth
5 out of 5 average rating, 13 reviews"Periwinkle" ~ a Charming Oceanfront Cottage
Quick stats about holiday rentals in Portland
Total rentals
1.6K properties
Total number of reviews
172K reviews
Family-friendly rentals
850 properties are a good fit for families
Pet-friendly rentals
450 properties allow pets
Rentals with a pool
60 properties have a pool
Rentals with dedicated workspaces
800 properties have a dedicated workspace
Destinations to explore
- Condo rentals Portland
- Rentals with an EV charger Portland
- Rentals with a fire pit Portland
- Beach house rentals Portland
- Rentals with a patio Portland
- Kid-friendly rentals Portland
- Apartment rentals Portland
- Rentals with a hot tub Portland
- Family-friendly rentals Portland
- Cottage rentals Portland
- Rentals with outdoor seating Portland
- Rentals with beach access Portland
- Rentals with a fireplace Portland
- Fitness-friendly rentals Portland
- Villa rentals Portland
- Pet-friendly rentals Portland
- Rentals with a sauna Portland
- Mansion rentals Portland
- Waterfront rentals Portland
- Beachfront rentals Portland
- House rentals Portland
- Private suite rentals Portland
- Rentals with a washing machine and dryer Portland
- Cabin rentals Portland
- Rentals with pools Portland
- Rentals with breakfast Portland
- Townhouse rentals Portland
- Rentals with a kayak Portland
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- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- Popham Beach State Park
- Long Sands Beach
- Surfside Beach
- Pemaquid Beach
- Ferry Beach
- Funtown Splashtown USA
- East End Beach
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- Wentworth by the Sea Country Club
- Dunegrass Golf Club
- Fox Ridge Golf Club
- Palace Playland
- Brunswick Golf Club
- King Pine Ski Area
- Wolfe's Neck Woods State Park
- Crescent Beach
- Pebbly Beach
- Purity Spring Resort
- Things to do Portland
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- Sightseeing Portland
- Tours Portland
- Things to do Cumberland County
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