147+ Private Villas and Holiday Rentals in South Portland |
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South Portland Holiday Rentals

About Casai's Private Villas and Holiday Rentals in South Portland

Discover more than 147 vacation rentals available in South Portland. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in South Portland.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in South Portland, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near South Portland. On average, places to stay near South Portland offer 645.79 ft², with nightly prices averaging ZA R5,140.

With Casai, finding and comparing holiday rentals in South Portland is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in South Portland

Type Count
Vacation Homes 58
Holiday Apartments 30
Cottages 3

Use these Quick Filters to Find a Holiday Rental in South Portland

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in South Portland.

Weather in South Portland, ME

View the weather forecast for South Portland before booking your South Portland Vacation Rentals to confirm your best time to go.

December - February
High 38°F       Low 16°F
March - May
High 61°F       Low 21°F
June - August
High 79°F       Low 55°F
September - November
High 74°F       Low 29°F

Top Attractions Around South Portland, ME

Casai offers a large selection of top attractions around South Portland . Research things to do on your vacation before you visit South Portland.


Maine Mall
Willard Beach
Bug Light
Southern Maine Community College
Maine Military Museum
Lyric Music Theater
Portland Harbor Museum
Spring Point Ledge Lighthouse
South Portland Historical Society Museum
Fort Preble
Sable Oaks Golf Course
Casco Bay Bridge
House Island
No Slack! Sportfishing Charters
Maine Medical Center
Old Orchard Beach Pier
Higgins Beach
Goose Rocks Beach
State Theatre
Cross Insurance Arena

Other Places to Stay in South Portland, ME


Bug Light 761 Properties
South Portland Historical Society Museum 750 Properties
No Slack! Sportfishing Charters 735 Properties
Portland Harbor Museum 731 Properties
Spring Point Ledge Lighthouse 723 Properties
Fort Preble 715 Properties
Southern Maine Community College 714 Properties
Knightville 655 Properties
Meetinghouse Hill 636 Properties
Loveitts Field 623 Properties
Cash Corner 62 Properties
Willard 25 Properties

Frequently Asked Questions About South Portland?

What are the top holiday rentals in South Portland?

With numerous options available in South Portland, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in South Portland:

How many holiday rentals have private pools in South Portland?

Discover a selection of holiday rentals with private pools near South Portland with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in South Portland are best for families?

If you're searching for a family-friendly holiday home in South Portland, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in South Portland:

How many Casai.co.za holiday rentals are available in South Portland?

As of 2026, Casai boasts over 147 properties listed in the South Portland area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in South Portland.

Nearby Neighborhood (6) 
Neighborhood Property Count
Cash Corner Vacation Rentals in Portland, Maine 62
Willard Vacation Rentals in Portland, Maine 25
Meetinghouse Hill Vacation Rentals in Portland, Maine 636
Loveitts Field Vacation Rentals in Portland, Maine 623
Knightville Vacation Rentals in Portland, Maine 655
Ferry Village Vacation Rentals in Portland, Maine 712

People Also Ask

There are 147 South Portland, ME Holiday Rentals

Recently Booked Holiday Rentals in South Portland