South Portland Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Browse Select South Portland Vacation Homes

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Fridge, microwave, oven, stovetop

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

9.8 out of 10, Exceptional, (50)
"We enjoyed ourselves very much! Close to everything we wanted to do. Would stay again."
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Maine Cottage
Property grounds

Maine Cottage

9.8 out of 10, Exceptional, (82)
"We loved everything about our stay! "
Maine Cottage
Sunny Modern Oasis in Portland’s Trendy East End
Exterior detail

Sunny Modern Oasis in Portland’s Trendy East End

10.0 out of 10, Exceptional, (53)
"This apartment was very clean, modern, and fairly private, located on a quite street, but still close enough to walk to shops, cafes, breweries. Only about half a mile from downtown. Would definitely stay again!"
Sunny Modern Oasis in Portland’s Trendy East End
Beachfront, Just steps and you're on the beach!
On the beach

Beachfront, Just steps and you're on the beach!

10.0 out of 10, Exceptional, (1)
"We loved our stay at the cottage. It was exceptionally clean and quiet. "
Beachfront, Just steps and you're on the beach!
Elegant and efficient Island home 4 miles from downtown Portland
Outdoor dining

Elegant and efficient Island home 4 miles from downtown Portland

Elegant and efficient Island home 4 miles from downtown Portland
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
1 bedroom, in-room safe, free WiFi, bed sheets

Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was as described, clean, and in a quiet neighborhood. Conveniently located to many local attractions. Check in and check out process was smooth. Overall enjoyed my stay very much. "
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
Quaint Cottage Vacation
Exterior

Quaint Cottage Vacation

9.0 out of 10, Wonderful, (28)
"Had a great time!!"
Quaint Cottage Vacation
Charming 110-year former Inn 10' from the Ocean!
Property grounds

Charming 110-year former Inn 10' from the Ocean!

9.8 out of 10, Exceptional, (128)
"We loved our stay here. Everything was clean. My kids loved the toy blocks and running out on the beach. There is a playground nearby on the beach. Views are amazing and the area is very quiet. Great vacation!"
Charming 110-year former Inn 10' from the Ocean!
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
Smart TV, video games, table tennis, books

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

8.2 out of 10, Very good, (54)
"We had a large group and had more than enough beds and plenty of space to hang out. Would recommend for a big group or a family looking to spread out!"
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
Luxurious Penthouse with Modern Design in Downtown
Interior

Luxurious Penthouse with Modern Design in Downtown

9.8 out of 10, Exceptional, (12)
"Just as advertised, would definitely stay here again. Great location!"
Luxurious Penthouse with Modern Design in Downtown
Swim, Kayak & Relax in Coastal Comfort from this Charming, Pet-Friendly Home
3 bedrooms, iron/ironing board, travel crib, free WiFi

Swim, Kayak & Relax in Coastal Comfort from this Charming, Pet-Friendly Home

10.0 out of 10, Exceptional, (1)
"Wonderful place to stay provided so many amenities. Beautiful views of Curtis Bay. Would definitely come back! "
Swim, Kayak & Relax in Coastal Comfort from this Charming, Pet-Friendly Home
Spacious 5BR Family Dream with Private Beach Access
Private kitchen

Spacious 5BR Family Dream with Private Beach Access

10.0 out of 10, Exceptional, (1)
"Great property! Spacious and comfortable.Nice location."
Spacious 5BR Family Dream with Private Beach Access
New South Portland Cottage, 10 Minutes to Downtown, Great for Entertaining
Exterior

New South Portland Cottage, 10 Minutes to Downtown, Great for Entertaining

9.6 out of 10, Exceptional, (65)
"We thoroughly enjoyed our stay at the Portland Cottage! It was a wonderful location, extremely clean, and incredible cozy. Paul is a delightful host!"
New South Portland Cottage, 10 Minutes to Downtown, Great for Entertaining
Charming 2-bedroom house with AC, WiFi in lovely Falmouth
Property grounds

Charming 2-bedroom house with AC, WiFi in lovely Falmouth

10.0 out of 10, Exceptional, (2)
"We had a wonderful stay. Nice comfortable camp. We enjoyed swimming in the lake. "
Charming 2-bedroom house with AC, WiFi in lovely Falmouth
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
Private kitchen

Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

2.0 star property
8.8 out of 10, Excellent, (6)
The price is CA $2,068
CA $3,004 total
includes taxes & fees
Aug 17 - Aug 18
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
Luxury 5BR/5 ensuite baths • Oceanfront retreat directly on the beach !
Dining

Luxury 5BR/5 ensuite baths • Oceanfront retreat directly on the beach !

Luxury 5BR/5 ensuite baths • Oceanfront retreat directly on the beach !
Enchanting 3BR Farmhouse Retreat Nature Getaway
Fridge, microwave, oven, stovetop

Enchanting 3BR Farmhouse Retreat Nature Getaway

10.0 out of 10, Exceptional, (3)
"We really enjoyed this property. It was very clean, and very comfortable. We will visit again. "
Enchanting 3BR Farmhouse Retreat Nature Getaway
ENJOY YOUR SUMMER AT BEACH ROSE COTTAGE IN OLD ORCHARD BEACH!
Beach nearby, beach towels

ENJOY YOUR SUMMER AT BEACH ROSE COTTAGE IN OLD ORCHARD BEACH!

9.8 out of 10, Exceptional, (45)
"Cleanest and updated house we have stayed in, I highly recommend. "
ENJOY YOUR SUMMER AT BEACH ROSE COTTAGE IN OLD ORCHARD BEACH!
The Lori House in Westbrook
Fridge, microwave, oven, stovetop

The Lori House in Westbrook

10.0 out of 10, Exceptional, (1)
The Lori House in Westbrook
Charming 3-bedroom house steps to Pine Point Beach with backyard oasis
Outdoor dining

Charming 3-bedroom house steps to Pine Point Beach with backyard oasis

2.0 star property
10.0 out of 10, Exceptional, (1)
"Perfect x 3Perfect location Perfect communication with owner Perfect homeFantastic home at Pine Point Maine that has everything you need for your stay. "
Charming 3-bedroom house steps to Pine Point Beach with backyard oasis
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top South Portland Hotel Reviews

Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

10/10 Excellent
"I enjoyed my stay and thought was excellent value for the money. For old property it has been kept up well. I enjoyed they had pool and strong AC in the rooms. "
Elizabeth 1-night trip
Posted 1 day ago
Days Inn by Wyndham Airport/Maine Mall