This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
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South Portland Vacation Rentals Show this location only Back to top
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Adorable, Light-Filled Bungalow Near Beaches and Downtown - Pet Ok!
2BR/2BA
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Sleeps 4
– South Portland #973608ha
$136 - $214 per night
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The Birdhouse at Willard Beach ~ a Maine Cottage at the Beach
2BR/1.5BA
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Sleeps 4-5
– South Portland #953622ha
$129 - $185 per night
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Romantic Maine Family Cottage Near Sandy Beach
3BR/1BA
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Sleeps 4-6
– South Portland #466164
$150 - $200 per night 2 night min stay
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Steps from
Willard Beach with Ocean Views.
1BR/1BA
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Sleeps 2
– South Portland #12490
$125 - $157 per night 4-7 night min stay
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Memorial Day Weekend Sale $1000 Private House 3br2ba, Sleeps 10, 500' from Beach
3BR+/2BA
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Sleeps 8-10
– South Portland #307943
From $157- $400/nt. Weekly discounts.
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Be Near Willard Beach on a Budget
1BR/1BA
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Sleeps 2
– South Portland #411440
$75 - $82 per night 3-7 night min stay
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Five Minute Walk to Willard Beach. Quiet Yet Fun, Seaside Area
3BR+/1BA
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Sleeps 4-6
– South Portland #281502
$175 - $199 per night 2 night min stay
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Contemporary Beach House
3BR+/2BA
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Sleeps 3-6
– South Portland #295408
$1100/wk - 1400wk
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2 Bedroom Oceanside Rental - Dog Friendly
2BR/2.25BA
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Sleeps 2-4
– South Portland #401572
$1,250/wk
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Oceanside Carriage House/ Dog Friendly -
1BR/1BA
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Sleeps 2
– South Portland #239255
$965/wk
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Enjoy Panoramic Views of the Southern Maine Coast in Quaint Old Orchard Beach
Studio/0BA
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Sleeps 2-4
– South Portland #471483
$2000 - $6000 per month 30 night min stay
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Spectacular Oceanfront Setting-Swimming - House with All Amenities
5BR/2.5BA
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Sleeps 8
– South Portland #115234ha
$343 - $429 per night
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10' from the Beach (Willard)
3BR/1BA
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Sleeps 7
– South Portland #243041ha
$65 - $329 per night
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Breathtaking Ocean Views from Portland's Victorian Terrace on the Prom
2BR/1.5BA
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Sleeps 4
– South Portland #935454ha
$320 - $357 per night 5-7 night min stay
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Spacious Oceanfront Home Perfect for Family Gatherings!
6BR/4BA
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Sleeps 12
– South Portland #327401ha
$843 per night
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Portland's Best Luxury Furnished Rentals
2BR/2BA
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Sleeps 4
– South Portland #235479ha
$80 - $271 per night
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Historic West End Apartment
1BR+/1BA
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Sleeps 3-4
– South Portland #184002ha
$725 - $825 per week 7 night min stay
- Modern House with Views of Casco Bay Islands ! Winter Rental September 1st 201 4BR/3BA – Sleeps 8 – South Portland #227492ha
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Elegant 1870 Carriage House in Exclusive West End
2BR+/2.5BA
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Sleeps 6
– South Portland #3489488ha
$350 per night 2 night min stay
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Delightful, Family-Friendly Home in Welcoming Portland Neighborhood
3BR/2.5BA
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Sleeps 6
– South Portland #990232ha
$195 per night 4 night min stay
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Modern, Airy Apartment in Portland's Desirable East End
2BR/1BA
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Sleeps 3
– South Portland #983767ha
$136 per night
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Grand Family Home, Newly Renovated with Private Beach Rights
6BR/4.5BA
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Sleeps 12
– South Portland #246160ha
$5950 per week 7 night min stay
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The Pilot House in South Portland
2BR/1BA
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Sleeps 6
– South Portland #961086ha
$129 - $195 per night
- Cape Elizabeth's Finest Oceanfront Rental Home for Your Vacation 4BR+/2.5BA – Sleeps 10 – South Portland #234306ha
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Newly Updated and Furnished Willard Beach Cottage
3BR/2BA
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Sleeps 8
– South Portland #175199ha
$60 - $286 per night
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Historic Intown Brick Victorian in Portland's Arts District
1BR/1BA
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Sleeps 2-3
– South Portland #386411ha
$167 - $250 per night
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Sophisticated Downtown Condo 5 Night Minimum
2BR/1BA
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Sleeps 4-5
– South Portland #3538570ha
$200 - $300 per night 5 night min stay
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Morning on the Promenade...Your Home Away from Home!
2BR/1BA
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Sleeps 4
– South Portland #976959ha
$63 - $214 per night
- New Rental Near Willard Beach with Views of Ocean South Portland 3BR/1.5BA – Sleeps 8 – South Portland #982636ha
- Beautifully Renovated East End Apartment with Casco Bay Views 2BR/1BA – Sleeps 3 – South Portland #181867ha
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Portland Apartment
1BR/1BA
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Sleeps 2
– South Portland #981922ha
$165 per night 2 night min stay
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Exquisite Victorian on Portlands East End
3BR/4BA
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Sleeps 6
– South Portland #3472391ha
$167 - $429 per night
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Adorable, Light-Filled Bungalow Near Beaches and Downtown - Pet Ok!
2BR/2BA
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Sleeps 4
– South Portland #973608ha
Overview of South Portland Vacation Rentals
Activities are Just Steps Away From South Portland Vacation Rentals
If you're looking for things to do in South Portland, you won't have a hard time creating a list of fun activities. Just a few minutes from your South Portland lodging, you'll find enough to keep you busy. The Sable Oaks Golf Course, one of the top-rated golf courses in the U.S., is just the beginning of the available activities in the area. Spas and other paths to living in luxury will give you a chance to unwind. Enjoy the Portland Mall's fantastic shopping opportunities, the Bean Outdoor Discovery School, or kayaking in Casco Bay. Put all of this within reach by booking South Portland vacation rentals.
History and Culture Near South Portland Lodging
South Portland is a region that's full of history. Casco Bay cottages put you in the midst of it. Go sightseeing at places like the Cotton Garden of Portland, Spring Point Ledge Lighthouse, the Greenwood Garden, Victoria Mansion, the Clay City Redux, or the famous Evergreen Cemetery. In addition to historic sites like these, cultural experiences abound at places like the Longhorn Steakhouse, Ricetta's Brickoven Pizzeria, and the Ginger Pad.
Casco Bay Cottages for Less
High quality South Portland lodging may be less expensive than you think. When you're traveling with a large group, like a big family, or if your vacation lasts for more than a few days, you'll notice a difference in price with Casco Bay cottages when compared to hotels. This better price doesn't mean that you're sacrificing creature comforts. The amenities at South Portland vacation rentals surpass those offered by luxury hotels and include kitchens, washer and dryer units, and everything else that you need to feel at home during vacation. Beyond luxury and price, the increased privacy of South Portland vacation rentals gives you a sense of intimacy that you simply can't find at local hotels.