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Vacation Homes in South Portland

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

9.8 out of 10, Exceptional, (48)
"Very nice property to stay at in Old Orchard Beach! It’s a very quiet neighborhood with a fully enclosed backyard, which was nice for my dog. It’s only a 15 minute walk to the beach, which is very convenient as well. Only thing that I would have liked was to have access to regular cable on the tv, since I couldn’t watch NESN with Roku. But still would give this place 5 stars! We had a lovely time. 😊"
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Maine Cottage

9.8 out of 10, Exceptional, (79)
"We loved everything about our stay! "
Maine Cottage

Sunny Modern Oasis in Portland’s Trendy East End

10.0 out of 10, Exceptional, (51)
"We loved our stay in Munjoy Hill at Mark's VRBO property! It was super clean and modern and in a fantastic location. We were able to walk all over the city from here! Close to so many great restaurants. It was also super private--loved the little deck off the back and the changing leaves. Would definitely stay here again!"
Sunny Modern Oasis in Portland’s Trendy East End

Convenient Portland home 3 miles from Downtown

10.0 out of 10, Exceptional, (27)
"The home was in a great neighborhood and the place was very clean. My family and I enjoyed staying here."
The price is AED 1,201
AED 2,891 total
includes taxes & fees
7 Aug - 8 Aug
Convenient Portland home 3 miles from Downtown

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!

Cozy and Quiet Beautiful Home One Bedroom Private Bathroom in Portland Maine.

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 Beautiful Home One Bedroom Private Bathroom in Portland Maine.

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

8.4 out of 10, Very Good, (53)
"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!

Quaint Cottage Vacation

9.0 out of 10, Wonderful, (25)
"Had a great time!!"
Quaint Cottage Vacation

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

9.8 out of 10, Exceptional, (126)
"John was great and the view was a amazing"
Charming 110-year former Inn 10' from the Ocean!

Luxurious Penthouse with Modern Design in Downtown

9.8 out of 10, Exceptional, (11)
"Just as advertised, would definitely stay here again. Great location!"
Luxurious Penthouse with Modern Design in Downtown

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

9.6 out of 10, Exceptional, (64)
"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

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

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

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

10.0 out of 10, Exceptional, (1)
"We had a wonderful stay. Nice comfortable camp. We enjoyed swimming in the lake. "
Charming 2-bedroom house with AC, WiFi in lovely Falmouth

Enchanting 3BR Farmhouse Retreat Nature Getaway

10.0 out of 10, Exceptional, (2)
"The home and property were beautifully maintained and exceptionally clean. Thoughtful touches throughout include plenty of k-cups, super soft towels in the bathrooms, travel size shampoo, conditioner, and lotion, laundry detergent, and throw blankets in the living room. The only thing I would warn people about is the traffic noise. If that is something you’re sensitive to, bring ear plugs for sleeping. Otherwise, it’s perfect. Very comfortable furniture and the hosts obviously put a lot of...
Enchanting 3BR Farmhouse Retreat Nature Getaway

The Lori House in Westbrook

10.0 out of 10, Exceptional, (1)
The Lori House in Westbrook

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

10.0 out of 10, Exceptional, (43)
"Cleanest and updated house we have stayed in, I highly recommend. "
ENJOY YOUR SUMMER AT BEACH ROSE COTTAGE IN OLD ORCHARD BEACH!

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 AED 5,510
AED 7,583 total
includes taxes & fees
17 Aug - 18 Aug
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

Water-view retreat with beach access, deck, grill, EV charger & lawn games

9.8 out of 10, Exceptional, (18)
"The house was fantastic. Serene, clean and beautiful setting. Would stay here again and again."
Water-view retreat with beach access, deck, grill, EV charger & lawn games

The Outlet Studio, Rustic Comfort w Fireplace

10.0 out of 10, Exceptional, (9)
"This is such a cozy little place just a short walk from all the fun in Freeport, and a quick ride to the highway. The apartment is warm and inviting. A really great place to stay."
The Outlet Studio, Rustic Comfort w Fireplace
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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