Book Holiday Homes in South Portland

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Featured Holiday Homes in South Portland

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

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

2 out of 5
Scarborough
Stay at this vacation home in Scarborough. Enjoy in-room jetted tubs and air conditioning. Popular attractions Engine and Grand Beach are located nearby.
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)

Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)

Buxton
Stay at this vacation home in Buxton. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attraction Swan Pond is located nearby.
Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)
The Moonglow! A beautiful ocean view house in Biddeford!

The Moonglow! A beautiful ocean view house in Biddeford!

Biddeford
Stay at this vacation home in Biddeford. Enjoy patios, cable/satellite TV service, and air conditioning. Popular attractions Engine and The Pool are located ...
The Moonglow! A beautiful ocean view house in Biddeford!
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Beach House ∆ Prime Location ∆ Steps to the Ocean

Beach House ∆ Prime Location ∆ Steps to the Ocean

Old Orchard Beach
The price is NZ$861 per night from 5 Jan to 6 Jan
NZ$861
includes taxes & fees
5 Jan - 6 Jan 2025
Book a stay at this beach vacation home in Old Orchard Beach. Enjoy free WiFi, a beach locale, and balconies. Popular attractions Engine and Old Orchard Beach ...
Beach House ∆ Prime Location ∆ Steps to the Ocean
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Portland
Book a stay at this family-friendly vacation home in Portland. Enjoy free WiFi, a water park, and a garden. Popular attractions Maine Mall and Deering Oaks Park ...
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Lakefront House

Lakefront House

Windham
The price is NZ$1,367 per night from 20 Jan to 21 Jan
NZ$1,367
includes taxes & fees
20 Jan - 21 Jan 2025
Stay at this vacation home in Windham. Enjoy free WiFi, a garden, and patios. Popular attractions Maine Wildlife Park and MAGAN Trailhead are located ...
Lakefront House
Beautiful Combo Home Located in Downtown Portland - Close to the Beach

Beautiful Combo Home Located in Downtown Portland - Close to the Beach

Portland
Stay at this vacation home in Portland. Enjoy a water park, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Maine Mall and Maine ...
Beautiful Combo Home Located in Downtown Portland - Close to the Beach
Charming 110-year former Inn 10' from the Ocean!

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

South Portland
Book a stay at this beach vacation home in South Portland. Enjoy free WiFi, a beach locale, and a water park. Popular attractions Maine Mall and Willard Beach ...
Charming 110-year former Inn 10' from the Ocean!
Immaculate Beachfront Retreat with Chef’s Kitchen, Ocean Vistas & Firepit

Immaculate Beachfront Retreat with Chef’s Kitchen, Ocean Vistas & Firepit

Scarborough
Book a stay at this beach vacation home in Scarborough. Enjoy a beach locale, a garden, and patios. Popular attractions Grand Beach and Pine Point Beach are ...
Immaculate Beachfront Retreat with Chef’s Kitchen, Ocean Vistas & Firepit
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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.

South Portland Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our South Portland vacation homes are the perfect way for you to wing it.

Holiday houses in South Portland let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of South Portland in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local South Portland adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in South Portland with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of South Portland vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

South Portland Holiday Homes essential information

Accommodation
582 Holiday Homes
Lowest Price
NZ$137
Highest Price
NZ$1,367
Popular accommodation
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough, Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option), The Moonglow! A beautiful ocean view house in Biddeford!, Beach House ∆ Prime Location ∆ Steps to the Ocean, Spacious & Sunny 4 Bedroom Close to Downtown, hot tub, Lakefront House, Beautiful Combo Home Located in Downtown Portland - Close to the Beach, Charming 110-year former Inn 10' from the Ocean!, Immaculate Beachfront Retreat with Chef’s Kitchen, Ocean Vistas & Firepit

Top trending hotels in South Portland

Casco Bay Hotel, Ascend Hotel Collection

Casco Bay Hotel, Ascend Hotel Collection

3.5 out of 5
80 John Roberts Rd., South Portland, ME
Fully refundableReserve now, pay when you stay
The price is NZ$163 per night from 5 Jan to 6 Jan
NZ$163
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this 3.5-star business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Casco Bay Hotel, Ascend Hotel Collection
Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

2.5 out of 5
369 Maine Mall Road, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is NZ$156 per night from 1 Jan to 2 Jan
NZ$156
includes taxes & fees
1 Jan - 2 Jan 2025
Stay at this hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Tru by Hilton Portland Airport Area
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
363 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is NZ$146 per night from 2 Jan to 3 Jan
NZ$146
includes taxes & fees
2 Jan - 3 Jan 2025
Stay at this hotel in South Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. ...
DoubleTree by Hilton Hotel Portland
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Comfort Inn Airport

Comfort Inn Airport

2.5 out of 5
90 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is NZ$137 per night from 25 Dec to 26 Dec
NZ$137
includes taxes & fees
25 Dec - 26 Dec
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
Comfort Inn Airport
Don't see what you're looking for?
See all available properties in South Portland
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.