5 Best Vacation Rentals in South Portland - Holiday Lettings - Cabins

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168 Vacation rentals

(3) Very Good 

31

Vacation apartment in South Portland

Maine / South Portland

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Minimal And Clean - Ready For Travellers This second floor apartment - with its two bedrooms, one bathroom, kitchen, and more - offers plenty of space for up to four guests. Minimal, clean, and carefully appointed with traveller necessities. Guests have access to two …see more

from $200 / night

$1,275 / week

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Responds fast!
avg. 3 hours 7 minutes

from $200 / night

56

Vacation home with golf nearby in South Portland

Maine / South Portland

4 13 Min stay varies

  • 4 bedrooms
  • Sleeps 13
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
This beautifully renovated house was stripped down to the studs for a full-scale renovation. Beautifully designed and completely renovated by a highly recognized designer, the house retains the original 1906 Dutch Colonial charm, but was creatively reimagined for today' …see more

from $545 / night

$3,775 - $7,900 / week

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Responds fast!
avg. 3 hours 55 minutes

from $545 / night

(1) Excellent 

13

Vacation studio in South Portland

Maine / South Portland

Studio 3 7 nights min

  • Studio
  • Sleeps 3
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Perfect for a Maine summer vacation. This completely renovated, 400 sq foot studio apartment is one house away from Willard Beach, 4 blocks to Willard Square, 1 mile from downtown South Portland, and a 5 minute drive to downtown Portland, ME. The apartment has a ful …see more

from $210 / night

$1,300 / week

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Responds fast!
avg. 1 hour 20 minutes

from $210 / night

22

Vacation home with golf nearby in South Portland

Maine / South Portland

3 4 3 nights min

  • 3 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
My home is brand new and was completed at the end of the Summer in 2015. I designed and furnished the home with a lot of thought, attention to detail and aesthetic appeal. Floors are hardwood and Carrara marble in two baths and Brazilian black slate in the half bath. …see more

from $400 / night

$2,800 / week

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from $400 / night

(3) Excellent 

72

Home rental in South Portland

Maine / South Portland

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
BRAND NEW TO MARKET! Accepting winter thru fall reservations now. Beautifully renovated 3 Bedroom, 1.5+ bath turn-of-the-century seaside home features beautiful views of the Portland shipping channel and the islands of Casco Bay and is just 100 yards to Willard Beac …see more

from $295 / night

$1,575 - $4,375 / week

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Responds fast!
avg. 3 hours 55 minutes

from $295 / night

14

Vacation home in South Portland

Maine / South Portland

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Child friendly
Enjoy this quaint cape cod style house. A fun eclectic space to land after a day of shopping in Portland's Old Port, the Maine Mall, the infamous Freeport LL Bean, or dinner out in one of downtown Portland's stellar restaurants. 3 Bedrooms, 1 Bathroom, House features …see more

from $300 / night

$2,100 / week

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Responds fast!
avg. 2 hours 56 minutes

from $300 / night

9

Vacation apartment in South Portland

Maine / South Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
If you'd prefer being walking distance to Portland's best beaches and parks, but want a modern, sleek and private apartment, look no further. Accommodating up to 2x couples or a small family, our recently renovated apartment is ready for your stay. Our place is just 20 …see more

from $115 / night

$600 - $1,390 / week

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from $115 / night