Compare Vacation Rentals & Airbnb in South Portland, ME

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South Portland, ME vacation rentals
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469 Rentals and Airbnb in South Portland, ME

Best family friendly South Portland, ME vacation rentals

Among the 469 accommodations in South Portland, ME, here are the 4 best family friendly rentals

Casco Bay Hideaway - South Portland, ME
10 25 reviews
South Portland, ME
12/07 – 17/07
$487/nighttotal: $2435 (5 )

Casco Bay Hideaway

1 1
apartment , South Portland
This South Portland apartment, ideally located near local restaurants and a short drive (distance unspecified) from Portland city centre, offers easy access to the beaches of South Portland and Cape Elizabeth.
The two-bedroom, one-bathroom flat sleeps three comfortably, boasting a modern kitchen with stainless steel appliances, Garnet Hill bedding, and digital locks for enhanced security.
Guesthouse Retreat Just Minutes From The Beaches! - South Portland, ME
South Portland, ME
13/10 – 25/10
$443/nighttotal: $5316 (12 )

Guesthouse Retreat Just Minutes From The Beaches!

1 2
apartment , Scarborough
This apartment is located in a rural setting in Scarborough, 6.4 kilometres from the town's beaches and a short drive from Prouts Neck, Portland Headlight, and Downtown Portland.
This 84 square metre apartment, suitable for up to three guests, offers one bedroom, one bathroom, a fully equipped kitchen with a dishwasher, air conditioning, a private deck with marsh views, and is equipped with internet and parking, with a pack n play and highchair available on request.
Newly Renovated, Classy, And Elegant! - South Portland, ME
9.9 363 reviews
South Portland, ME
21/08 – 24/08
$1946/nighttotal: $5838 (3 )

Newly Renovated, Classy, And Elegant!

5 4
apartment , Portland
This stylish flat is located just a short distance from downtown Portland, making it easy to explore the city's attractions and amenities. It has consistently received excellent ratings for cleanliness, location, and overall experience.
The two-bedroom flat comfortably accommodates couples or small families. It comes equipped with a modern kitchen, a comfortable living area with a large TV, and a private terrace, making it a great choice for a relaxing stay.
West End's Diamond In The Rough 2-bedroom Apartment With Parking & Wifi - South Portland, ME
10 16 reviews
South Portland, ME
13/10 – 25/10
$530/nighttotal: $6360 (12 )

West End's Diamond In The Rough 2-bedroom Apartment With Parking & Wifi

2 2
apartment , Portland
This West End Portland apartment, boasting a 98 Walkscore and 95 Bikescore, offers easy access to Thompson's Point, Old Orchard Beach, Bayside Bowl, and the Southworth Planetarium (distances not specified).
The two-bedroom, one-bathroom flat sleeps four, features a fully equipped kitchen with gas stove, refrigerator, microwave, and essential baby equipment available on request, and includes a designated parking space (compact cars only).

Best South Portland, ME vacation rentals with a pool

Among the 469 accommodations in South Portland, ME, here are the 4 best rentals with a pool

Apt In Victorian Mansion W/ Hot Tub, Parking, Pool - South Portland, ME
9.9 496 reviews
South Portland, ME
12/07 – 17/07
$463/nighttotal: $2315 (5 )

Apt In Victorian Mansion W/ Hot Tub, Parking, Pool

1 1
apartment , Portland
This charming apartment is located in Portland, just minutes from the bustling downtown area and within easy reach of the Old Port, Fore River hiking path and Capisic Pond Park. The property has consistently received excellent ratings for its location, cleanliness and user experience.
The apartment offers a private entrance and living area, perfect for a group of four. Guests can enjoy a range of amenities including a shared pool, hot tub, fire pits, a spacious garden, a well-equipped kitchen and a private piano.
Tower Suite Plus: Hot Tub, W/d, Parking, Spa Bath - South Portland, ME
9.9 77 reviews
South Portland, ME
21/08 – 24/08
$692/nighttotal: $2076 (3 )

Tower Suite Plus: Hot Tub, W/d, Parking, Spa Bath

1 4
apartment , Portland
This charming apartment is situated in a historic Victorian house in Portland, just 6 kilometres from the city centre and 3 kilometres from the airport and train station. It has received excellent ratings for its location, cleanliness, and overall experience.
The apartment is spacious and comfortably accommodates up to four guests, with two bedrooms, a modern bathroom, and a lounge/kitchenette. Guests can enjoy access to a shared hot tub, outdoor fire pit, and a large garden with picnic tables, as well as a Level 2 EV charging station.
Gorgeous 3-bedroom House With A Pool In Charming Portland - South Portland, ME
South Portland, ME
13/10 – 25/10
$957/nighttotal: $11484 (12 )

Gorgeous 3-bedroom House With A Pool In Charming Portland

3 2
apartment , Portland
This Portland property is situated in the North Deering neighbourhood, offering proximity to cultural sites such as Thompson's Point and the Maine Narrow Gauge Railroad, with Southworth Planetarium and Portland Observatory also nearby.
This three-bedroom flat accommodates up to six guests and features a private outdoor space with a swimming pool, garden, and barbecue, alongside essential amenities like air conditioning, internet, and parking.
Portland Pool House - Minutes To The Old Port! - South Portland, ME
South Portland, ME
13/10 – 25/10
$884/nighttotal: $10608 (12 )

Portland Pool House - Minutes To The Old Port!

3 2
house , Portland
This Portland holiday home is located a short drive from the Old Port, offering convenient access to downtown attractions and beaches.
This detached house offers 200 square metres of air-conditioned living space with two bedrooms, two bathrooms, a kitchen, and a terrace, accommodating up to 11 guests with a private swimming pool and Wi-Fi.

Frequently Asked Questions about vacation rentals in South Portland, ME

  • When is the best time to book a vacation rental in South Portland, ME?

    The summer months are the busiest time for tourism in South Portland, so if you're looking for the best deals, it's best to book your vacation rental in the spring or autumn. The shoulder seasons offer a more relaxed atmosphere and you'll have less competition for the best rentals.
  • What are the best Airbnb and vacation rentals in South Portland, ME?

    Apartment Walking Distance To Willard Beach, Charming 110-year Former Inn 10' From The Ocean and Willard Beach: Cozy Apartment With A King Size Bed are the most popular Airbnb and vacation rentals in South Portland, ME among travelers.

  • What are the best budget-friendly activities in South Portland, ME?

    Take a stroll along the Eastern Promenade, a scenic park with stunning views of the city and the harbour. Grab a picnic lunch and enjoy the fresh air. The South Portland Public Library also offers a variety of free events and programs, including book clubs, lectures, and movie screenings. And of course, you can always enjoy a free walk along the beautiful coastline.
  • What are the most popular Airbnbs in South Portland, ME?

  • What are the best restaurants with local dishes in South Portland, ME?

    The Lobster Shack at Two Lights is a popular spot for fresh seafood, they have a great selection of lobster rolls and other Maine classics. For something a bit more casual, you can try the South Portland House of Pizza, they have a great menu of pizzas, subs and salads.
  • What are the best vacation rentals with a pool in South Portland, ME?

  • What are the best walking or cycling routes in South Portland, ME?

    The Eastern Promenade is a great place for a walk or bike ride, it offers stunning views of the city and the harbour. The South Portland Land Trust also has a network of trails that are perfect for exploring the local area. If you're looking for a longer ride, you can cycle along the Eastern Promenade Trail, it's a 4.5km paved trail that runs along the waterfront.
  • What are the best rentals for families and kids in South Portland, ME?

  • Are there pet-friendly attractions in South Portland, ME?

    Many of the beaches in South Portland are dog-friendly, including Willard Beach State Park. The South Portland Land Trust also has a number of trails that are open to dogs, just make sure to keep them on a leash.
  • What are the best rentals or Airbnbs with a jacuzzi in South Portland, ME?

  • What are the benefits of choosing a vacation rental in South Portland, ME?

    Vacation rentals offer more space and privacy than a hotel room, and they're often a more affordable option, especially if you're travelling with a family or a group of friends. You also have the convenience of being able to cook your own meals and do your own laundry.
  • What are the top sports attractions and facilities in South Portland, ME?

    The South Portland Recreation Department offers a range of sports facilities, including a public swimming pool, a fitness centre and a number of sports fields. The city is also home to the South Portland High School, which has a number of sports teams, including football, basketball and baseball.

Destinations nearby

Best South Portland, ME vacation rentals with a balcony

Salt Water Breeze - South Portland, ME
South Portland, ME
12/07 – 17/07
$489/nighttotal: $2445 (5 )

Salt Water Breeze

1 1
apartment , Old Orchard Beach
This Old Orchard Beach flat offers direct access to a balcony with sea views, located an 11-minute walk from Palace Playland and close to Pirate's Cove and the Old Orchard Beach Pier, with Portland International Jetport Airport 21 kilometres away.
This 38 square metre studio apartment accommodates up to 7 guests, featuring a well-equipped kitchen with a microwave, fridge and stovetop, a satellite flat-screen TV, private entrance, and access to a children's playground and outdoor furniture.
Centrally Located Off Back Cove, 1st Floor 4 Bedroom, 1.5 Bath Condo W/ Porch - South Portland, ME
9.0 2 reviews
South Portland, ME
12/07 – 17/07
$2245/nighttotal: $11225 (5 )

Centrally Located Off Back Cove, 1st Floor 4 Bedroom, 1.5 Bath Condo W/ Porch

4 1
apartment , Portland
This four-bedroom Portland condo, near Forest Avenue and Woodfords Corner, is a short walk from the Back Cove Trail and a 3.2-kilometre drive from Portland's Old Port.
The self-catering apartment sleeps up to twelve guests, features a fully equipped kitchen, outdoor grill, off-street parking for two cars, and offers convenient access to local amenities including The Great Lost Bear and Woodfords Corner.
Little Miss Cottages - Two Bedroom Cottage Suite - 9 - South Portland, ME
South Portland, ME
12/07 – 17/07
$1143/nighttotal: $5715 (5 )

Little Miss Cottages - Two Bedroom Cottage Suite - 9

2 1
house , Old Orchard Beach
This cottage in Old Orchard Beach is a 9-minute walk from the Pier and 0.7 kilometres from Pirate's Cove.
This property offers 2 bedrooms, 1 bathroom, sleeps 13 guests, and features a garden, balcony, on-site water park, and complimentary WiFi.
Enjoy The Good Life. Free Parking, Ac In Bedroom. - South Portland, ME
South Portland, ME
13/10 – 25/10
$1026/nighttotal: $12312 (12 )

Enjoy The Good Life. Free Parking, Ac In Bedroom.

1 2
apartment , Portland
This Portland flat is situated 7 minutes' walk from the Portland Museum of Art and 1.4 kilometres from the historic Portland Downtown Historic District, offering convenient access to local attractions.
This 37 square metre apartment accommodates two guests with one bedroom and one bathroom, featuring air conditioning, a private balcony, complimentary Wi-Fi, and a kitchen equipped with a fridge, microwave, and dishwasher.

Best South Portland, ME vacation rentals with parking

Sandy Toes - South Portland, ME
South Portland, ME
12/07 – 17/07
$495/nighttotal: $2475 (5 )

Sandy Toes

2 1
apartment , Old Orchard Beach
Sandy Toes is a holiday flat situated in Old Orchard Beach, a 9-minute walk from the Old Orchard Beach Pier and 6.77 kilometres from Funtown Splashtown USA.
This accommodation offers 43 square meters of living space, accommodating up to 4 guests in 2 bedrooms, and includes a kitchen with a fridge and microwave oven, an on-site restaurant, a children's playground, and outdoor furniture.
Charming Private 1st Floor Studio Apartment - South Portland, ME
South Portland, ME
13/10 – 25/10
$226/nighttotal: $2712 (12 )

Charming Private 1st Floor Studio Apartment

1 2
studio , Portland
This one-bedroom flat is located in Portland's Oakdale district, offering proximity to Thompson's Point, Old Orchard Beach, and the Old Orchard Beach Pier, with easy access to Southworth Planetarium and Bayside Bowl.
This pet-friendly apartment accommodates up to three guests, featuring a queen bed, air conditioning, heating, a fridge, and a microwave, with parking and a garden available.
South Portland  Beach Area Rental - South Portland, ME
10 1 review
South Portland, ME
13/10 – 25/10
$541/nighttotal: $6492 (12 )

South Portland Beach Area Rental

1 2
apartment , South Portland
This South Portland flat is located in the Willard Beach district, just a stone's throw from the shoreline and within 3 kilometres of downtown Portland, with convenient access to local cafés and the Maine Mall.
This one-bedroom flat for two guests offers a kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace/balcony, garden access, and dedicated parking, with nearby opportunities for motor boating, fishing, swimming, and cycling.
Beach Across The Street Pet Friendly Sleeps 3 - South Portland, ME
South Portland, ME
12/07 – 17/07
$434/nighttotal: $2170 (5 )

Beach Across The Street Pet Friendly Sleeps 3

1 1
house , Old Orchard Beach
This Old Orchard Beach holiday cottage is located directly opposite the beach, a 9-minute walk to the Old Orchard Beach Pier and close to Palace Playland.
This 475 square meter holiday home accommodates up to 5 guests, features 1 bedroom, 1 bathroom, air conditioning, free Wi-Fi, a kitchen with a fridge and microwave, and a garden with a patio, with free private parking available.
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