Book Holiday Homes in South Portland

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Featured Holiday Homes in South Portland

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

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

Cumberland
With a stay at this vacation home, you'll be centrally located in Cumberland Center, within a 15-minute drive of Thompson's Point and Casco Bay.
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!
The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries

Portland
With a stay at this vacation home, you'll be centrally located in Portland, within a 10-minute drive of Thompson's Point and Maine Mall.
The Globe House on Munjoy Hill - Walk to Breweries
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
With a stay at this vacation home in Scarborough (Grand Beach), you'll be within a 5-minute drive of Old Orchard Beach Pier and Old Orchard Beach.
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
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New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Bailey Island
With a stay at this vacation home in Bailey Island, you'll be on the beach, just steps from Casco Bay and a 2-minute drive from Bailey Island Bridge.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
The Moonglow! A beautiful ocean view house in Biddeford!

The Moonglow! A beautiful ocean view house in Biddeford!

Biddeford
When you stay at this vacation home in Biddeford, you'll be near the beach, within a 5-minute drive of Fortunes Rock Beach and Saint Brendan's Chapel.
The Moonglow! A beautiful ocean view house in Biddeford!
Rent a room in the gorgeous Holt House

Rent a room in the gorgeous Holt House

Portland
With a stay at this vacation home in Portland (Parkside), you'll be a 3-minute drive from Thompson's Point and 8 minutes from Maine Mall.
Rent a room in the gorgeous Holt House
Sensational Beachfront Property Old Orchard Beach, Maine, with indoor elevator

Sensational Beachfront Property Old Orchard Beach, Maine, with indoor elevator

Old Orchard Beach
The price is AU$2,036 per night from 17 Mar to 18 Mar
AU$2,036
includes taxes & fees
17 Mar - 18 Mar
When you stay at this vacation home in Old Orchard Beach, you'll be on the beach, just steps from Old Orchard Beach and 15 minutes by foot from Old Orchard Beach ...
Sensational Beachfront Property Old Orchard Beach, Maine, with indoor elevator
Serenity between the lakes and seashore

Serenity between the lakes and seashore

Westbrook
With a stay at this vacation home in Westbrook, you'll be within a 15-minute drive of Maine Mall and Thompson's Point.
Serenity between the lakes and seashore
Modern & Sunny House Steps from the Promenade. Private Parking!

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

Portland
The price is AU$569 per night from 16 Mar to 17 Mar
AU$569
includes taxes & fees
16 Mar - 17 Mar
With a stay at this vacation home, you'll be centrally located in Portland, within a 10-minute drive of Thompson's Point and Maine Mall.
Modern & Sunny House Steps from the Promenade. Private Parking!
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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
602 Holiday Homes
Lowest Price
AU$131
Highest Price
AU$2,036
Popular accommodation
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!, The Globe House on Munjoy Hill - Walk to Breweries, Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough, New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach, The Moonglow! A beautiful ocean view house in Biddeford!, Rent a room in the gorgeous Holt House, Sensational Beachfront Property Old Orchard Beach, Maine, with indoor elevator, Serenity between the lakes and seashore, Modern & Sunny House Steps from the Promenade. Private Parking!

Top trending hotels in South Portland

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 AU$154 per night from 26 Mar to 27 Mar
AU$154
includes taxes & fees
26 Mar - 27 Mar
When you stay at DoubleTree by Hilton Hotel Portland in South Portland, you'll be near the airport, a 1-minute drive from Maine Mall and 8 minutes from Thompson's ...
DoubleTree by Hilton Hotel Portland
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 AU$146 per night from 24 Mar to 25 Mar
AU$146
includes taxes & fees
24 Mar - 25 Mar
When you stay at Tru by Hilton Portland Airport Area in South Portland, you'll be near the airport, a 1-minute drive from Maine Mall and 7 minutes from Thompson's ...
Tru by Hilton Portland Airport Area
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 AU$131 per night from 17 Mar to 18 Mar
AU$131
includes taxes & fees
17 Mar - 18 Mar
When you stay at Comfort Inn Airport in South Portland, you'll be in a shopping district, a 1-minute drive from Maine Mall and 6 minutes from Thompson's ...
Comfort Inn Airport
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Quality Inn & Suites

Quality Inn & Suites

2.5 out of 5
738 Main Street, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$137 per night from 28 Mar to 29 Mar
AU$137
includes taxes & fees
28 Mar - 29 Mar
Located in South Portland, Quality Inn & Suites is a 4-minute drive from Maine Mall and 6 minutes from Maine Medical Center.
Quality Inn & Suites
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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.

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^Subject to availability and chosen travel dates.