Holiday Homes in South Portland

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in South Portland and around

Willard Beach–Private Apt Near Portland & Parks
Interior

Willard Beach–Private Apt Near Portland & Parks

10.0 out of 10, Exceptional, (2)
"Excellent in every way."
The price is €230
includes taxes & fees
15 Sept - 16 Sept
Willard Beach–Private Apt Near Portland & Parks
Spacious and Centrally Located! Two Connected Apartments- Sleeps 12
Private kitchen

Spacious and Centrally Located! Two Connected Apartments- Sleeps 12

The price is €617
includes taxes & fees
2 Sept - 3 Sept
Spacious and Centrally Located! Two Connected Apartments- Sleeps 12
Willard Square Family Home
Property grounds

Willard Square Family Home

9.6 out of 10, Exceptional, (7)
"A funky place. Liked the decor. "
The price is €742
includes taxes & fees
17 Aug - 18 Aug
Willard Square Family Home
Modern Getaway by the Sea
Fridge, microwave, oven, stovetop

Modern Getaway by the Sea

The price is €506
includes taxes & fees
14 Sept - 15 Sept
Modern Getaway by the Sea
Willard Beach: Cozy Apartment with a King Size Bed
Fridge, microwave, oven, stovetop

Willard Beach: Cozy Apartment with a King Size Bed

10.0 out of 10, Exceptional, (1)
"Lovely and quiet. Just what I had hoped for. "
The price is €268
includes taxes & fees
10 Sept - 11 Sept
Willard Beach: Cozy Apartment with a King Size Bed
Full sized home
Interior

Full sized home

9.8 out of 10, Exceptional, (32)
"Very clean and comfortable. Great care has gone into making it feel like a home well loved."
The price is €319
includes taxes & fees
19 Aug - 20 Aug
Full sized home
The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury
Fridge, microwave, oven, stovetop

The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury

10.0 out of 10, Exceptional, (1)
"We had a fantastic stay at this peaceful oceanside property in Harpswell, Maine. The setup—with a main house, attached apartment, and a charming bunkhouse—was perfect for our two families and adult children. There was plenty of space for everyone to relax and unwind.The backyard is absolutely stunning, filled with beautiful flowers and lush grass, and it opens up to a tranquil ocean inlet. We especially loved the hammock spot, perfect for a good book or an afternoon nap, and the back porch...
The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury
Classic New England Waterfront
Private kitchen

Classic New England Waterfront

Classic New England Waterfront
Bird Watching Paradise @ Waterfront Harpswell with Private Deck
Private kitchen

Bird Watching Paradise @ Waterfront Harpswell with Private Deck

10.0 out of 10, Exceptional, (1)
"Super location, very private, responsive host, lovely, clean. Very lucky to have been able to stay here!"
The price is €535
includes taxes & fees
16 Aug - 17 Aug
Bird Watching Paradise @ Waterfront Harpswell with Private Deck
Waterfront Spacious Luxury Home, 5 min to LL Bean!
Exterior

Waterfront Spacious Luxury Home, 5 min to LL Bean!

9.8 out of 10, Exceptional, (20)
"Great place. Gracious hosts. Warm and cozy space with plenty of room for everyone. "
Waterfront Spacious Luxury Home, 5 min to LL Bean!
Waterfront, Luxury, Spacious home in Freeport!
Terrace/patio

Waterfront, Luxury, Spacious home in Freeport!

10.0 out of 10, Exceptional, (27)
"Great location - close to downtown Freeport. Beautiful property with plenty of comfortable sleeping options"
Waterfront, Luxury, Spacious home in Freeport!
30 Acres with Woodland Trails and Playground
Fridge, microwave, oven, stovetop

30 Acres with Woodland Trails and Playground

2.0 star property
10.0 out of 10, Exceptional, (1)
"Spent a week with my family at this lovely property in Freeport, ME. The location is ideal to visit various attractions nearby. Including the pinturesque dowtown. The house was clean and had everything needed to have a pleasant stay away from home. "
30 Acres with Woodland Trails and Playground
Luxury King Room with Parlor and Balcony
Property grounds

Luxury King Room with Parlor and Balcony

The price is €615
includes taxes & fees
7 Sept - 8 Sept
Luxury King Room with Parlor and Balcony
Spacious Country Home Freeport, Only 5 min to LL Bean!
Interior

Spacious Country Home Freeport, Only 5 min to LL Bean!

9.6 out of 10, Exceptional, (15)
"We had a great time here. It was great."
Spacious Country Home Freeport, Only 5 min to LL Bean!
Charming Studio apartment with WiFi, AC in welcoming Portland
Interior

Charming Studio apartment with WiFi, AC in welcoming Portland

9.6 out of 10, Exceptional, (5)
"This was a great stay through and through. Excellent condition, very responsive before and during the stay, and a great location. 10/10 will recommend to anyone staying in Portland! "
The price is €200
includes taxes & fees
20 Aug - 21 Aug
Charming Studio apartment with WiFi, AC in welcoming Portland
Charming 2-bedroom apartment with AC, WiFi in fabulous Portland
Interior

Charming 2-bedroom apartment with AC, WiFi in fabulous Portland

6.0 out of 10, (1)
"The location was very convenient. I missed the part that said it was on second floor with a curved stair case. The actual apartment was clean, but in need of a few repairs. "
The price is €378
includes taxes & fees
27 Aug - 28 Aug
Charming 2-bedroom apartment with AC, WiFi in fabulous Portland
Spacious 4-bedroom house located in the heart of Portland, ME.
Interior

Spacious 4-bedroom house located in the heart of Portland, ME.

10.0 out of 10, Exceptional, (1)
"Clean, comfortable. "
The price is €873
includes taxes & fees
1 Sept - 2 Sept
Spacious 4-bedroom house located in the heart of Portland, ME.
Mint Ocean Promenade Condo, Steps to Old Port
Private kitchen

Mint Ocean Promenade Condo, Steps to Old Port

10.0 out of 10, Exceptional, (1)
The price is €308
includes taxes & fees
2 Sept - 3 Sept
Mint Ocean Promenade Condo, Steps to Old Port
Modern & Sunny House Steps from the Promenade. Private Parking!
Terrace/patio

Modern & Sunny House Steps from the Promenade. Private Parking!

10.0 out of 10, Exceptional, (29)
"Perfect stay for a quick trip to Portland! "
The price is €532
includes taxes & fees
10 Sept - 11 Sept
Modern & Sunny House Steps from the Promenade. Private Parking!
Elegant condo - walk to Portland's best restaurants & Old Port
Fridge, microwave, oven, stovetop

Elegant condo - walk to Portland's best restaurants & Old Port

9.4 out of 10, Exceptional, (62)
"Right off a Main Street with tons of food and drink options. Loved the area, felt safe and fun. Close to walking trails as well. Inside decor was nice. "
The price is €375
includes taxes & fees
17 Aug - 18 Aug
Elegant condo - walk to Portland's best restaurants & Old Port
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

Clarion Hotel Portland

Clarion Hotel Portland

10/10 Excellent
"Convenient, good location "
Neal 1-night trip
Posted 1 day ago
Clarion Hotel Portland