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

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11 Vacation rentals

(1) Very Good 

24

Vacation home in South Portland

Maine / South Portland

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
This brand-new, 1,000-square-foot home built for two offers modern appliances and designer decor as well as cutting edge in-home entertainment and access to a private beach a short drive away. Located on Cape Elizabeth, just 10 minutes from downtown Portland, you're clo …see more

from $162 / night

$1134 / week

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Responds fast!
avg. 3 hours 42 minutes

from $162 / night

13

Vacation studio in South Portland

Maine / South Portland

Studio 3 3 nights min

  • Studio
  • Sleeps 3
  • 3 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 $195 / night

$1200 / week

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Responds fast!
avg. 1 hour 59 minutes

from $195 / night

(3) Very Good 

27

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 $150 / night

$1033 / week

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Responds fast!
avg. 3 hours 36 minutes

from $150 / 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

$2800 / week

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from $400 / night

(2) Excellent 

67

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

$1575 - $5215 / week

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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

$2100 / week

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Responds fast!
avg. 1 hour 42 minutes

from $300 / night

(1) Excellent 

13

South Portland Vacation cottage rental

Maine / South Portland

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
This unique ocean side carriage house is just one house from the ocean. It has one bedroom with a king size bed. A full bath and kitchen. All linens, plates, utensils and glassware included. Air conditioned. Our beach is a quiet, sandy, mile long neighborhood beach on …see more

from $190 / night

$1350 - $2050 / week

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from $190 / night

21

Vacation home in South Portland

Maine / South Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
You'll be only one block from Willard Beach at this two-bedroom South Portland condo, a charming and comfortable getaway with a dog-friendly interior, a private outdoor deck, and a wonderful location near lighthouses, shops, restaurants, and the gorgeous shores of Casco …see more

from $85 / night

$595 / week

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Responds fast!
avg. 3 hours 42 minutes

from $85 / night

20

Vacation home in South Portland

Maine / South Portland

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Enjoy a revitalizing retreat to the charming city of Portland when you stay at this lovely vintage condo. You'll have updated amenities inside, plus a deck and gas grill, and you'll be in close proximity to lots of restaurants nearby in Willard Square. Conveniently loca …see more

from $88 / night

$616 / week

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Responds fast!
avg. 3 hours 42 minutes

from $88 / night

6

Home rental in South Portland

Maine / South Portland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
For an amazing stay in a lively area of Portland, this inviting dog-friendly condo has plenty to offer. You'll have a wood stove, a great deck with a gas grill, and a top-notch location within walking distance to lots of fantastic eateries. Located in the heart of Willa …see more

from $80 / night

$560 / week

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Responds fast!
avg. 3 hours 42 minutes

from $80 / night

4

Vacation home in South Portland

Maine / South Portland

4 13 3 nights min

  • 4 bedrooms
  • Sleeps 13
  • 3 nights min
  • Child friendly
This Beautiful new vacation home is the latest creation of the group at Sopo Cottage and has already received national media attention. This four bedroom, 2.5 bath home is 2125 square feet and features some of the original 1906 beach house features, while creatively re …see more

from $895 / night

$6976 / week

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from $895 / night