Discover Your Perfect South Portland Vacation Homes

South Portland Luxury Rentals

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South Portland Pet Friendly Vacation Rentals

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South Portland Large Vacation Homes

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Why Choose Rent By Owner for your South Portland Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for South Portland Vacation Rentals

Where are the best neighborhoods to stay in South Portland?

When choosing where to stay in South Portland, Maine, exploring its diverse neighborhoods can greatly enhance your visit. Each area offers unique charm and convenient access to local amenities, making it easy to find the ideal location for your trip. Whether you prefer a bustling neighborhood close to the waterfront or a quieter community nestled inland, South Portland's neighborhoods provide a variety of options that cater to different travel styles. With dependable vacation rentals available throughout the area, you can enjoy a comfortable and seamless stay in this welcoming coastal community.

Cash Corner

Discover a convenient and welcoming area that offers easy access to local amenities and transportation, making it an ideal base for exploring the region. Here, you can enjoy comfortable accommodations close to the heart of South Portland.

View 66+ Rentals in Cash Corner

Knightville

This vibrant neighborhood boasts a mix of charming shops and friendly community spaces, perfect for those who want to immerse themselves in the lively local scene. Staying in this area means being close to popular dining and entertainment options.

View 573+ Rentals in Knightville

Meetinghouse Hill

Perched on a scenic hillside, this neighborhood offers tranquility alongside convenient access to the city's attractions, making it an excellent choice for visitors seeking comfort and accessibility. It’s an ideal spot for relaxing stays while exploring here.

View 552+ Rentals in Meetinghouse Hill

Willard

Known for its peaceful streets and friendly atmosphere, this neighborhood provides a quiet retreat within reach of downtown amenities. It’s suited for travelers looking for a restful stay with easy access to the area's highlights.

View 34+ Rentals in Willard

Ferry Village

Nestled along the waterfront, this charming area is perfect for those wanting to enjoy scenic views and a relaxed pace. Staying here grants you proximity to the water while remaining close to key attractions.

View 593+ Rentals in Ferry Village

Loveitts Field

This open, inviting neighborhood offers spacious surroundings and easy access to outdoor activities, making it an appealing choice for nature lovers. It provides a peaceful environment where you can unwind after a day of exploring.

View 539+ Rentals in Loveitts Field

Best Times to Visit South Portland

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here can enhance your experience, allowing you to enjoy the area's unique charm while making the most of your vacation rental in South Portland, Maine, USA.

Peak Season Highlights

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Summer (June to August)

During the summer months, the area experiences warm weather ideal for outdoor activities and exploring local scenery.

Average Temperature Daytime: around 75-85°F - Nighttime: approximately 55-65°F
autumn
Fall (September to October)

Autumn attracts visitors with its vibrant foliage and crisp air, making it a popular time for sightseeing and outdoor adventures.

Average Temperature Daytime: about 65-70°F - Nighttime: roughly 45-55°F

Off-Season Highlights

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Early Winter (November to December)

The quiet early winter period offers peaceful surroundings before the holiday rush, perfect for those seeking tranquility in the region.

Average Temperature Daytime: around 40-50°F - Nighttime: near 30-40°F
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Late Winter (January to February)

During the colder months, you can enjoy fewer crowds and a cozy atmosphere, ideal for indoor relaxation or winter sports nearby.

Average Temperature Daytime: approximately 30-40°F - Nighttime: around 20-30°F

Weekly Weather Forecast for South Portland

How to Book Your South Portland Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in South Portland

More Top-Rated Vacation Rentals in South Portland Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor patio or balcony for relaxing outside amidst the fresh coastal air.
  • Take advantage of well-maintained gardens or landscaped yards that provide a peaceful outdoor setting.
  • Stay active with access to scenic walking or jogging paths nearby, perfect for exploring the region’s natural beauty.
  • Make the most of outdoor dining areas, ideal for enjoying meals with views of the surrounding area.
  • Relax by a shared or private outdoor pool, especially during warmer months in this seaside destination.
  • Utilize outdoor grilling stations or BBQ facilities to experience a classic Maine cookout.
  • Benefit from convenient parking options with designated outdoor spaces for your vehicle, providing ease of access here in the region.

Top Attractions Around South Portland

What attractions are nearby?

In this welcoming area, you can enjoy a variety of outdoor activities, local dining experiences, and scenic waterfront views just moments from your South Portland vacation rental.

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Family Activities

  • Willard Beach:** Enjoy a family day at this scenic beach where you can relax, build sandcastles, and explore the tide pools along the shoreline.
  • South Portland Historical Society Museum:** Discover local history through engaging exhibits that are perfect for curious minds of all ages.
  • Bug Light Park:** Visit this picturesque park featuring a historic lighthouse, scenic views, and open space ideal for picnics and outdoor activities.
  • Palace Playland:** Experience classic seaside fun with amusement rides and games that will delight children and parents alike in this well-loved coastal amusement park.
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Adult Activities

  • Fort Williams Park: Stroll through this scenic park to enjoy spectacular views of the Atlantic Ocean and explore iconic landmarks like the Portland Head Light.
  • Maine Mall: Shop at the region’s largest retail destination, offering a diverse range of stores, dining options, and entertainment for a relaxing day out.
  • Cooking Classes: Join local culinary experiences that highlight regional flavors, perfect for those interested in Maine’s distinctive cuisine.
  • Portland Harbor Cruises: Embark on a boat tour to admire the stunning coastline and learn about the area's maritime history from the water.

Other Places to Stay in South Portland, ME

Bug Light
Bug Light Vacation Rentals
South Portland Historical Society Museum
South Portland Historical Society Museum Vacation Rentals
No Slack! Sportfishing Charters
No Slack! Sportfishing Charters Vacation Rentals
Portland Harbor Museum
Portland Harbor Museum Vacation Rentals
Spring Point Ledge Lighthouse
Spring Point Ledge Lighthouse Vacation Rentals
Fort Preble
Fort Preble Vacation Rentals
Southern Maine Community College
Southern Maine Community College Vacation Rentals
Knightville
Knightville Vacation Rentals
Meetinghouse Hill
Meetinghouse Hill Vacation Rentals
Loveitts Field
Loveitts Field Vacation Rentals
Cash Corner
Cash Corner Vacation Rentals
Willard
Willard Vacation Rentals
More Places to Stay Near South Portland

South Portland Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining and shopping: Take advantage of the area's vibrant waterfront and charming downtown to enjoy authentic Maine cuisine and unique boutiques near your vacation rentals.
  • Plan outdoor adventures: Make the most of the region's scenic parks and coastal spots by scheduling activities like walking, biking, or seaside strolls that highlight this destination’s natural beauty.
  • Visit seasonal events and festivals: Check out local events happening during your stay to immerse yourself in the community spirit and get a true feel for the area's cultural vibe.
  • Utilize nearby transportation options: Familiarize yourself with local transit routes or rental services to easily access popular sites and maximize your time exploring the region.

Transportation Options

  • Portland International Jetport: This regional airport offers convenient flights for travelers coming from various parts of the country and beyond, making your journey to the area seamless.
  • Amtrak Downeaster: Connecting you to Boston and other New England destinations, this train service provides a relaxing travel option close to your stay in the region.
  • Local Bus Services: Commuter buses and local transit options allow easy access around South Portland and neighboring areas, ideal for exploring without a car.
  • Taxi and Rideshare Services: Available throughout here, these services provide quick and convenient transportation, ensuring you can reach your vacation rental comfortably and on time.

Local Customs Options

  • Community Harbor Seal Watching: Engaging in local seal watching tours offers a unique way to connect with the area's rich marine life during your stay.
  • Folk Music Traditions: You can experience the region’s vibrant folk music scene at community gatherings that celebrate its maritime heritage.
  • Seafood Dining Etiquette: Appreciating the local seafood with respect to traditional dining customs enhances your culinary experience here.
  • Celebration of Lobster Festivals: Participating in annual lobster festivals allows you to immerse yourself in the region’s iconic fishing culture and community spirit.

Frequently Asked Questions About South Portland?

1. What are the top vacation rentals in South Portland?

There are a lot of options in South Portland. If you plan on staying in the South Portland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in South Portland:

2. How many vacation rentals have private pools in South Portland?

There are 5 vacation rentals with private pools near South Portland. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in South Portland are best for families?

If you are looking for a family-friendly vacation home in South Portland, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in South Portland:

4. How many Rentbyowner vacation rentals are available in South Portland?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 138 in the South Portland area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in South Portland. 

5. What is the cancellation policy for booking vacation rentals in South Portland, Maine?

Cancellation policies vary depending on the individual listing. It’s important to review the specific terms provided on the property’s page or contact the owner directly for detailed information about refunds and cancellation deadlines.

6. How do I verify the availability of a vacation rental in this area before booking?

Availability can be checked by viewing the calendar on the listing page. If you have special dates in mind, reaching out to the property owner can provide confirmation and any additional details you may need.

7. Are there any specific amenities I should expect in vacation rentals here?

Amenities differ among properties, so it’s best to consult each listing for details such as Wi-Fi, parking, kitchen facilities, or outdoor spaces. Owners typically highlight key features to help you choose the perfect stay.

8. What steps should I take to ensure a smooth check-in process in this destination?

Check the check-in instructions provided in the listing or communicate directly with the owner beforehand. Many hosts offer flexible check-in options; confirming details ahead of time can help ensure an easy arrival.

9. Is it safe to book vacation rentals through this platform in South Portland, Maine?

Yes, the platform screens listings and provides secure booking options. However, always read reviews and communicate with owners to confirm all details and ensure your peace of mind before finalizing your reservation.