We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers: Windows: Internet Explorer, Mozilla Firefox. Mac: Safari.

South Portland Holiday Rentals

Hotels (12)

B&Bs / Inns (0)

Speciality Lodging (0)

Holiday Rentals (5)

The safest rental experience online

Rent from verified owners and managers, and read reviews before you book.

Find out what to expect »

In partnership with:

Get listed

Add your property »

Other Destinations
Popular Maine Destinations
Bangor Holiday Rentals (5)
Bethel Holiday Rentals (8)
Kittery Holiday Rentals (3)
Ogunquit Holiday Rentals (44)
York Holiday Rentals (222)
Nearby listings
Y721, York
Y721
    Price: £611/week
  • Bedrooms: 3, sleeps 8
  • Bathrooms: 2
    • Contact Manager
Androscoggin Home Rentals, Bethel
Androscoggin Home Rentals
    Price: £107 - £214/night £550/week
  • Bedrooms: 5, sleeps 12
  • Bathrooms: 3
  • Min stay: 2
    • Contact Owner
Q965-A, Ogunquit
Q965-A
    Price: £87 - £105/night £611 - £733/week
  • Bedrooms: 1, sleeps 4
  • Bathrooms: 1
    • Contact Manager
Luxury Mountain Home At Sunday River, Bethel
Luxury Mountain Home At Sunday River
    Price: £244 - £427/night £1,528 - £2,994/week
  • Bedrooms: 6, sleeps 16
  • Bathrooms: 6
  • Min stay: 3
    • Contact Owner
Fall Line condo South 202 at Sunday River Ski Area, Bethel
Fall Line condo South 202 at Sunday River Ski Area
    Price: £79 - £122/night
  • Bedrooms: 1, sleeps 6
  • Bathrooms: 1
  • Min stay: 1
    • Contact Owner
Luxury, Grand 6500 sq. ft. Post & Beam Home with all of the amen, Bethel
Luxury, Grand 6500 sq. ft. Post & Beam Home with all of the amen
    Price: £4,583/week £19,642/month
  • Bedrooms: 5, sleeps 16
  • Bathrooms: 5
    • Contact Manager
In-Town 3 Bedroom Condominium, Bethel
In-Town 3 Bedroom Condominium
    Price: £107/night £642/week £1,242 - £1,346/month
  • Bedrooms: 3, sleeps 6
  • Bathrooms: 3
    • Contact Manager
2-Bedroom Eden Ridge Townhouse(4C), Bethel
2-Bedroom Eden Ridge Townhouse(4C)
    Price: £76/night £428/week £1,878/month
  • Bedrooms: 2, sleeps 6
  • Bathrooms: 1
    • Contact Manager
Y726, York
Y726
    Price: £917 - £1,528/week
  • Bedrooms: 4, sleeps 8
  • Bathrooms: 1
    • Contact Manager
Cape Neddick, York
Cape Neddick
    Price: Inquire for rates
  • Bedrooms: 4, sleeps 6
  • Bathrooms: 1
    • Contact Manager

Search South Portland Holiday Rentals

Clear dates

Advanced Search

Recommended by Travellers

[ Recommended ] [ Price / nt ] [ Price / wk ] [ Price / mo ] [ Bedrooms ]

There are no holiday rentals within South Portland, Maine. We broadened your search to include all rentals within 40 kilometers.

On Beach Time, Old Orchard Beach
On Beach Time
Contact Owner
4.5 of 5 stars 6 reviews
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 1, sleeps 5
Bathrooms: 1
Min stay:7
A beautiful, newly renovated 1 bedroom/1 bath condo in the heart of Old Orchard Beach. Bedroom has a queen size bed. Living room has a Queen size sleeper ...
  • Nightly
    --
  • Weekly
    £458 - £519
  • Monthly
    £428
Experience Life on a Maine Island, Peaks Island
Experience Life on a Maine Island
Contact Owner
Nightly rate from
£107
4 of 5 stars 1 review
Management: Verified Plus owner
Property: Holiday Rental House
Bedrooms: 2, sleeps 6
Bathrooms: 1
Min stay:3
Located on charming Peaks Island, this early-1900's home is the perfect island getaway. It holds the charm of a turn-of-the-century island cottage with the ...
  • Nightly
    £107 - £153
  • Weekly
    £489 - £794
  • Monthly
    --
Capt. Lawrence E. Johnson House, Bailey Island
Capt. Lawrence E. Johnson House
Contact Owner
4.5 of 5 stars 2 reviews
Management: Verified owner
Property: Holiday Rental House
Bedrooms: 5, sleeps 10
Bathrooms: 5
Min stay:7
Available now for weekly rentals and special events. The newly renovated Captain Lawrence E. Johnson House is available as a weekly luxury summer rental and ...
  • Nightly
    --
  • Weekly
    £2,139
  • Monthly
    --
Woodsea Place Real Log home Close to the Beach, Peaks Island
Woodsea Place Real Log home Close to the Beach
Contact Owner
Management: Verified owner
Property: Holiday Rental House
Bedrooms: 5, sleeps 15
Bathrooms: 2
Get away from it all! Near the sandy beach & boat club and on 1.5 acres you will be able to relax on the porch and enjoy the birds and unbelievable birch and ...
  • Nightly
    --
  • Weekly
    £1,833
  • Monthly
    --
OCEANFRONT ESTATE, PINE POINT-OLD ORCHARD BEACH, Scarborough
OCEANFRONT ESTATE, PINE POINT-OLD ORCHARD BEACH
Contact Owner
Nightly rate from
£214
Management: Verified Plus owner
Property: Holiday Rental House
Bedrooms: 4, sleeps 12
Bathrooms: 3
Spectacular ocean views of the entire Saco Bay and soft white sand at your feet from this 4 bedroom 3 bathroom home on the beach. Reserved parking, full ...
  • Nightly
    £214
  • Weekly
    £1,681
  • Monthly
    --
Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns