SOUTH PORTLAND, Maine

Vacation Rentals in SOUTH PORTLAND, Maine

Discover 26 vacation rental properties in SOUTH PORTLAND. From 1 to 3 bedrooms. Average $293/night. 100% have pools.

26 verified listings Book securely on VRBO Prices updated March 2026

26 properties available

Willard Beach Get Away - Dog Friendly - Steps from the shore!

Willard Beach Get Away - Dog Friendly - Steps from the shore!

1 bed 1 bath
PoolA/CWiFiBalcony
$260/night
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Willard Beach Neighborhood-Close to all Southern Maine has to offer!

Willard Beach Neighborhood-Close to all Southern Maine has to offer!

2 beds 1 bath
PoolA/CWiFiBalcony
$395/night
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Charming 110-year former Inn 10' from the Ocean!

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

3 beds 1 bath
PoolA/CWiFiBalcony
$351/night
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New South Portland Cottage, 10 Minutes to Downtown, Great for Entertaining

New South Portland Cottage, 10 Minutes to Downtown, Great for Entertaining

1 bed 1 bath
PoolA/CWiFiBalcony
$211/night
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Ocean views 30 Steps to Willard Beach! Amazing location 5-7 min to Portland.

Ocean views 30 Steps to Willard Beach! Amazing location 5-7 min to Portland.

2 beds 1 bath
PoolA/CWiFiBalcony
$552/night
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Ocean views 30 Steps to Willard Beach! Amazing location 5-7 min to Portland.

Ocean views 30 Steps to Willard Beach! Amazing location 5-7 min to Portland.

2 beds 1 bath
PoolA/CWiFiBalcony
$535/night
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Cozy, Pet Friendly, Home In A Quiet Family Oriented, Beach Neighborhood

Cozy, Pet Friendly, Home In A Quiet Family Oriented, Beach Neighborhood

2 beds 1 bath
PoolA/CWiFiBalcony
$301/night
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So. Po. Sweet Spot

So. Po. Sweet Spot

1 bed 1 bath
PoolA/CWiFiBalcony
$210/night
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Distinguished classic coastal home overlooks Casco Bay and Maine’s rocky shore!

Distinguished classic coastal home overlooks Casco Bay and Maine’s rocky shore!

3 beds 2 baths
PoolA/CWiFiBalcony
$753/night
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Willard Square Family Home

Willard Square Family Home

3 beds 2 baths
PoolA/CWiFiBalcony
$493/night
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Step right out the ocean is at your door! Amazing location and views!

Step right out the ocean is at your door! Amazing location and views!

2 beds 2 baths
PoolA/CWiFiBalcony
$132/night
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Enjoy a Hassle-Free and Suiting Stay! Pet-Friendly Property, Parking, Breakfast!

Enjoy a Hassle-Free and Suiting Stay! Pet-Friendly Property, Parking, Breakfast!

1 bed 1 bath
PoolA/CWiFiBalcony
$137/night
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Comfort and Convenience! Free Breakfast, Parking, Pet-Friendly Property!

Comfort and Convenience! Free Breakfast, Parking, Pet-Friendly Property!

1 bed 1 bath
PoolA/CWiFiBalcony
$142/night
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Maine Artist Retreat

Maine Artist Retreat

1 bed 1 bath
PoolA/CWiFiBalcony
$180/night
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Charming home, minutes away from downtown Portland, beaches, and the airport.

Charming home, minutes away from downtown Portland, beaches, and the airport.

3 beds 1 bath
PoolA/CWiFiBalcony
$265/night
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Look No Further! 2 Spacious Units, Complimentary Breakfast, Parking!

Look No Further! 2 Spacious Units, Complimentary Breakfast, Parking!

2 beds 2 baths
PoolA/CWiFiBalcony
$273/night
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Ideal Location! 2 Comfortable Units, Free Breakfast, Pets Allowed!

Ideal Location! 2 Comfortable Units, Free Breakfast, Pets Allowed!

2 beds 2 baths
PoolA/CWiFiBalcony
$283/night
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Beachside Condo with Private Terrace

Beachside Condo with Private Terrace

2 beds 1 bath
PoolA/CWiFiBalcony
$405/night
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Cozy Studio Apartment within walking distance to Willard Beach

Cozy Studio Apartment within walking distance to Willard Beach

1 bed 1 bath
PoolA/CWiFiBalcony
$113/night
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Newly Renovated Apartment in Willard Square Area of South Portland, Maine.

Newly Renovated Apartment in Willard Square Area of South Portland, Maine.

1 bed 1 bath
PoolA/CWiFiBalcony
$197/night
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Charming, updated 2 bdr Condo - Steps to the beach!

Charming, updated 2 bdr Condo - Steps to the beach!

2 beds 1 bath
PoolA/CWiFiBalcony
$345/night
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Comfortable cottage style home. Family friendly. Sleeps six.

Comfortable cottage style home. Family friendly. Sleeps six.

3 beds 3 baths
PoolA/CWiFiBalcony
$326/night
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Willard Beach, Sweet Two Bedroom House

Willard Beach, Sweet Two Bedroom House

2 beds 2 baths
PoolA/CWiFiBalcony
$123/night
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Willard Beach Bungalow

Willard Beach Bungalow

3 beds 1 bath
PoolA/CWiFiBalcony
$183/night
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Boho bungalow with designer touches 10 minutes to beaches and downtown Portland

Boho bungalow with designer touches 10 minutes to beaches and downtown Portland

2 beds 1 bath
PoolA/CWiFiBalcony
$201/night
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Stunning South Portland Apartment w/Pool

Stunning South Portland Apartment w/Pool

1 bed 1 bath
PoolA/CWiFiBalcony
$260/night
View Details → Book on VRBO

More destinations in Maine

Old Orchard Beach (413) Wells (400) Bar Harbor (311) York (302) Portland (294) Ogunquit (254) Kennebunkport (216) Boothbay Harbor (206) Southwest Harbor (199) Kennebunk (199) Newry (192) Ellsworth (136) Scarborough (132) camden (105) Greenville (104) Harpswell (97) Mount Desert (96) Bethel (94) Mt Desert (64) Boothbay (63)