South Portland Holiday Rentals

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Holiday Rentals in South Portland

Willard Beach–Private Apt Near Portland & Parks

10.0 out of 10, Exceptional, (1)
"Cozy and clean place with a quick walk to the beach in beautiful neighborhood!"
The price is NZ$641
includes taxes & fees
20 July - 21 July
Willard Beach–Private Apt Near Portland & Parks

Charming 3-bedroom house with WiFi, AC in serene South Portland

The price is NZ$752
includes taxes & fees
23 July - 24 July
Charming 3-bedroom house with WiFi, AC in serene South Portland

Willard Beach: Cozy Apartment with a King Size Bed

The price is NZ$694
includes taxes & fees
10 Aug - 11 Aug
Willard Beach: Cozy Apartment with a King Size Bed

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

The price is NZ$2,885
includes taxes & fees
21 July - 22 July
The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury

Classic New England Waterfront

The price is NZ$2,783
includes taxes & fees
19 July - 20 July
Classic New England Waterfront

Mere Point Sunrise Views at Eastern Shore!

9.8 out of 10, Exceptional, (6)
"Great property with a great view. No ac was a bummer Washing machine kept erroring out a few mins after starting Grill brush was broke upon arrival Grill was very dirty and starting grease fires, so we cleaned it May want to check leaking of kitchen sink or dishwasher. When washing clothes I noticed the ceiling is wet right under the kitchen sink area "
The price is NZ$855
includes taxes & fees
25 July - 26 July
Mere Point Sunrise Views at Eastern Shore!

Waterfront Spacious Luxury Home, 5 min to LL Bean!

9.8 out of 10, Exceptional, (18)
"Great place. Gracious hosts. Warm and cozy space with plenty of room for everyone. "
The price is NZ$1,714
includes taxes & fees
21 July - 22 July
Waterfront Spacious Luxury Home, 5 min to LL Bean!

Waterfront, Luxury, Spacious home in Freeport!

10.0 out of 10, Exceptional, (26)
"Great location - close to downtown Freeport. Beautiful property with plenty of comfortable sleeping options"
The price is NZ$5,112
includes taxes & fees
4 Aug - 5 Aug
Waterfront, Luxury, Spacious home in Freeport!

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

10.0 out of 10, Exceptional, (4)
"We had a wonderful time in Freeport, getting some Christmas season shopping in and bring our 4 year old to the Sparkle weekend festivities. "
The price is NZ$1,445
includes taxes & fees
27 July - 28 July
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!

9.8 out of 10, Exceptional, (31)
"I spent summers on Long Island in Casco Bay always dreaming of staying at Peak’s Island to see what all the hype was about… Well, it exceeded my expectations at this location! The communication with the owner, to the comfort of the cottage and view was priceless. We are already planning for next summer 😃"
The price is NZ$2,084
includes taxes & fees
4 Aug - 5 Aug
Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!

Charming Studio apartment with WiFi, AC in welcoming Portland

10.0 out of 10, Exceptional, (2)
"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 NZ$383
includes taxes & fees
28 July - 29 July
Charming Studio apartment with WiFi, AC in welcoming Portland

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 NZ$881
includes taxes & fees
11 Aug - 12 Aug
Charming 2-bedroom apartment with AC, WiFi in fabulous Portland

Mint Ocean Promenade Condo, Steps to Old Port

The price is NZ$760
includes taxes & fees
23 July - 24 July
Mint Ocean Promenade Condo, Steps to Old Port

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

10.0 out of 10, Exceptional, (29)
"This properly was perfectly suited for my wife and I, it is exactly as it is described. We were comfortable and enjoyed every minute at this property. We had to reschedule our flight which required us staying an extra night, Jennifer so graciously allowed us to stay another night. We would definitely stay here again if we ever return to Portland."
The price is NZ$1,149
includes taxes & fees
13 July - 14 July
Modern & Sunny House Steps from the Promenade. Private Parking!

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 NZ$1,094
includes taxes & fees
28 July - 29 July
Elegant condo - walk to Portland's best restaurants & Old Port

The Globe House on Munjoy Hill - Walk to Breweries

10.0 out of 10, Exceptional, (78)
"Great historic house in a terrific location. "
The price is NZ$1,136
includes taxes & fees
15 July - 16 July
The Globe House on Munjoy Hill - Walk to Breweries

Spacious Downtown Waterfront Unit | Pets Are Welcome | Parking!

10.0 out of 10, Exceptional, (4)
"Awesome location. Look forward to returning in the summer!"
The price is NZ$791
includes taxes & fees
20 July - 21 July
Spacious Downtown Waterfront Unit | Pets Are Welcome | Parking!

Relaxing Couple Pet-Friendly Stay | Seafood & Portland Attractions

9.0 out of 10, Wonderful, (4)
"The halls echo badly and the people who wanted to party on our floor were very loud into the early morning "
The price is NZ$726
includes taxes & fees
20 July - 21 July
Relaxing Couple Pet-Friendly Stay | Seafood & Portland Attractions

Brews, Art & Fun! Downtown Stay Right in the Heart of Portland!

9.0 out of 10, Wonderful, (19)
"We had a great "
The price is NZ$726
includes taxes & fees
20 July - 21 July
Brews, Art & Fun! Downtown Stay Right in the Heart of Portland!

Stylish Stay | Savor Seafood & Explore Portland’s History!

The price is NZ$791
includes taxes & fees
20 July - 21 July
Stylish Stay | Savor Seafood & Explore Portland’s History!
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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Frequently asked questions

Can I find holiday rentals in South Portland?

Yes, there are holiday rentals close to the most popular sights in South Portland, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in South Portland. Allow some time to check out the waterfront during your trip.

What are some of the best holiday rentals that South Portland has to offer?

Charming 3 bedroom lake house on Damariscotta Lake.: This holiday home rental outside of South Portland has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in South Portland?

With 56 Expedia holiday rentals, you're guaranteed to find just the right place for your South Portland stay.

What can I see and do in South Portland?

Cultural attractions include Lyric Music Theater and South Portland Historical Society Museum, whereas Willard Beach and Casco Bay are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Maine Mall and Bug Light.

What are holiday rentals like in South Portland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in South Portland. Holiday rentals feature extras like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family gatherings.