Search Holiday Rentals in South Portland

    price find illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Save instantly and earn perks with One Key
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Top Holiday Rentals in South Portland

Willard Beach: Cozy Apartment with a King Size Bed

Willard Beach: Cozy Apartment with a King Size Bed

Willard Square Family Home

9.6 out of 10, Exceptional, (7)
"A funky place. Liked the decor. "
The price is £510
includes taxes & fees
7 Jul - 8 Jul
Willard Square Family Home

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 £323
includes taxes & fees
20 Jul - 21 Jul
Willard Beach–Private Apt Near Portland & Parks

Full sized home

9.8 out of 10, Exceptional, (28)
"This property was as described and it felt like we were staying at a family member’s cozy house. The towels were thick, the beds were comfortable, and the kitchen had everything we needed."
The price is £276
includes taxes & fees
10 Jul - 11 Jul
Full sized home

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

The price is £1,306
includes taxes & fees
7 Jul - 8 Jul
The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury

Classic New England Waterfront

The price is £1,073
includes taxes & fees
7 Jul - 8 Jul
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 £356
includes taxes & fees
9 Jul - 10 Jul
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 £1,036
includes taxes & fees
21 Jul - 22 Jul
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 £2,272
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 £703
includes taxes & fees
27 Jul - 28 Jul
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

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 £173
includes taxes & fees
28 Jul - 29 Jul
Charming Studio apartment with WiFi, AC in welcoming Portland

2-bedroom apartment in Portland, ME with WiFi, AC. Enjoy your stay!

The price is £292
includes taxes & fees
4 Aug - 5 Aug
2-bedroom apartment in Portland, ME with WiFi, AC. Enjoy your stay!

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

The price is £403
includes taxes & fees
14 Jul - 15 Jul
Charming 2-bedroom apartment with AC, WiFi in fabulous Portland

Mint Ocean Promenade Condo, Steps to Old Port

The price is £289
includes taxes & fees
8 Jul - 9 Jul
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 £577
includes taxes & fees
8 Jul - 9 Jul
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 £337
includes taxes & fees
7 Jul - 8 Jul
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 Globe House on Munjoy Hill - Walk to Breweries

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 £329
includes taxes & fees
13 Jul - 14 Jul
Brews, Art & Fun! Downtown Stay Right in the Heart of Portland!

Relaxing Couple Pet-Friendly Stay | Seafood & Portland Attractions

8.8 out of 10, Excellent, (3)
"The halls echo badly and the people who wanted to party on our floor were very loud into the early morning "
The price is £329
includes taxes & fees
13 Jul - 14 Jul
Relaxing Couple Pet-Friendly Stay | Seafood & Portland Attractions

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 £358
includes taxes & fees
20 Jul - 21 Jul
Spacious Downtown Waterfront Unit | Pets Are Welcome | Parking!
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.
Save an average of 15% on thousands of hotels when you're signed in

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 110-year former Inn 10' from the Ocean!: This highly rated holiday home rental in South Portland is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in South Portland?

With 55 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.