South Portland vacation rentals

KAYAK searches hundreds of travel sites at once for vacation home deals in South Portland

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Useful Info
Recommended by KAYAK

Best South Portland vacation rentals

Go to map

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

$155 - $538$538 - $921$921 - $1,304$1,304 - $1,686$1,686+ per night

Property Types

ApartmentCondoCottageHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

Most recommended vacation rentals in South Portland

Show all
South Portland Cottage - South Portland - Living room
South Portland Cottage
South Portland, ME
9.1Wonderful(30)
$296+
Check availability
Cozy, Pet Friendly, Home In A Quiet Family Oriented, Beach Neighborhood - South Portland - Bedroom
Cozy, Pet Friendly, Home In A Quiet Family Oriented, Beach Neighborhood
South Portland, ME
10Wonderful(16)
Free Wi-Fi
$309+
Check availability
Sunny Spot with Private Parking. - South Portland - Living room
Sunny Spot with Private Parking.
South Portland, ME
9.8Wonderful(14)
$237+
Check availability
Ocean Views! Willard Beach Cottage~2 Min Walk To Beach, 9 Mins To Old Port. - South Portland - Living room
Ocean Views! Willard Beach Cottage~2 Min Walk To Beach, 9 Mins To Old Port.
South Portland, ME
Free Wi-Fi
$702+
Check availability
Ocean views 30 Steps to Willard Beach! Amazing location 7 min to Portland.Unit 2 - South Portland - Bedroom
Ocean views 30 Steps to Willard Beach! Amazing location 7 min to Portland.Unit 2
South Portland, ME
9.3Wonderful(3)
Free Wi-Fi
$446+
Check availability
Willard Beach Two Bedroom Cottage - October available at discount - South Portland - Dining room
Willard Beach Two Bedroom Cottage - October available at discount
South Portland, ME
$196+
Check availability
Willard Square Family Home - South Portland - Bedroom
Willard Square Family Home
South Portland, ME
9.5Wonderful(8)
Parking
Free Wi-Fi
Pet friendly
$482+
Check availability
Ocean Views, Rooftop Deck, Hot Tub, New Back Deck! 3-Min Walk To Willard Beach - South Portland - Bedroom
Ocean Views, Rooftop Deck, Hot Tub, New Back Deck! 3-Min Walk To Willard Beach
South Portland, ME
10Wonderful(1)
$1,211+
Check availability
Strawberry Hill - South Portland - Bedroom
Strawberry Hill
South Portland, ME
9.4Wonderful(19)
Parking
Free Wi-Fi
Pet friendly
$1,686+
Check availability
Charming 110-year former Inn 10' from the Ocean! - South Portland - Beach
Charming 110-year former Inn 10' from the Ocean!
South Portland, ME
9.9Wonderful(61)
Free Wi-Fi
$685+
Check availability
Comfortable cottage style home. Family friendly. Sleeps six. - South Portland - Patio
Comfortable cottage style home. Family friendly. Sleeps six.
South Portland, ME
9.7Wonderful(21)
$473+
Check availability
Arlies Digs One Block To Willard Beach - South Portland - Living room
Arlies Digs One Block To Willard Beach
South Portland, ME
9.9Wonderful(51)
Free Wi-Fi
Pet friendly
$412+
Check availability
Willard Beach Neighborhood-Close To All Southern Maine Has To Offer! - South Portland - Patio
Willard Beach Neighborhood-Close To All Southern Maine Has To Offer!
South Portland, ME
9.7Wonderful(18)
$398+
Check availability
Distinguished classic coastal home overlooks Casco Bay and Maine’s rocky shore! - South Portland - Living room
Distinguished classic coastal home overlooks Casco Bay and Maine’s rocky shore!
South Portland, ME
10Wonderful(3)
Free Wi-Fi
$692+
Check availability
Charming Craftsman Retreat- 5 minute walk to Willard Beach- 30 night minimum - South Portland - Dining room
Charming Craftsman Retreat- 5 minute walk to Willard Beach- 30 night minimum
South Portland, ME
Free Wi-Fi
$429+
Check availability
Willard Beach Get Away - Dog Friendly - Steps from the shore! - South Portland - Beach
Willard Beach Get Away - Dog Friendly - Steps from the shore!
South Portland, ME
10Wonderful(4)
Free Wi-Fi
$341+
Check availability
Useful Info

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

June
September
$493
$1,109
Cheapest month to stay with an average 74% drop in price.
Most expensive month to stay with an average 44% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding South Portland vacation rental deals

  • Pool is the most popular vacation rental property amenity in South Portland
  • Vacation rentals in South Portland are around 79% more expensive than hotels on average. Search here to compare prices for all accommodation types in South Portland.
  • The best vacation rental properties in South Portland are Arlies Digs One Block To Willard Beach (9.9, 51 reviews), Charming 110-year former Inn 10' from the Ocean! (9.9, 61), and Comfortable cottage style home. Family friendly. Sleeps six. (9.7, 21), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in South Portland, you should consider visiting during the low season. The cheapest vacation homes in South Portland can be found in June and July.
  • The cheapest night for renting a vacation home in South Portland is Monday. In contrast, the most expensive is Friday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in South Portland for 39 days.

Where to stay in South Portland?

Our map will help you find the perfect place to stay in South Portland by showing you the exact location of each vacation rental.

Everything you need to know for your stay in South Portland

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.