South Portland holiday lettings

We found 90 holiday rentals — enter your dates for availability

Discover a selection of 9 homes and other holiday rentals in South Portland that are perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the amenities that you need and want for your stay, which might include parking and a fireplace. You're sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.
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  • All the privacy of home

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Frequently asked questions

What is the most popular type of holiday rental in South Portland?
In South Portland, holiday houses are the most popular type of holiday rental, with around 16 available throughout the area. These homes typically feature multiple bedrooms, fully equipped kitchens, and spacious living areas, making them ideal for families or groups looking for a comfortable stay. Additionally, there are several condos available, which offer a more compact living space with amenities such as modern kitchens and access to shared facilities like pools or fitness centres.
How much does it cost to rent a holiday home in South Portland?
Prices for holiday rentals in South Portland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in South Portland to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for South Portland holiday house rentals?
You can find great discounts on house rentals in South Portland on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in South Portland?
In South Portland, popular rental amenities include balconies, fully equipped kitchens, coffee and tea makers, as well as dedicated workspaces with desks and desk chairs. These amenities cater to both leisure and business travellers, providing comfortable and functional spaces to relax or work.
Can I find family house rentals in South Portland?
In South Portland, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The neighbourhoods around the city, particularly near Willard Beach and the picturesque Cape Elizabeth area, offer spacious homes that cater to families. Many properties come equipped with full kitchens, allowing for easy meal preparation, as well as outdoor spaces where kids can play and adults can relax.

Additionally, visitors can enjoy amenities such as Wi-Fi and laundry facilities, which add to the convenience of the stay. Proximity to local parks, such as the scenic Fort Williams Park with its iconic lighthouse, provides ample opportunities for outdoor activities and family outings.
Are there any South Portland holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in South Portland with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I book pet-friendly holiday rentals in South Portland?
In South Portland, you can find several pet-friendly holiday rentals that cater to travellers with furry companions. The area offers a variety of accommodation options, including charming cottages and modern apartments, many of which feature essential amenities such as fully equipped kitchens, outdoor spaces, and comfortable living areas. These rentals often provide a friendly setting for both guests and their pets.

South Portland is conveniently located near several parks that are great for pet owners. The expansive Mill Creek Park, for example, features walking paths and open green spaces where dogs can enjoy a run or a leisurely stroll. Additionally, the nearby South Portland Dog Park is a dedicated space for dogs to socialise and play off-leash, making it an excellent destination for pet enthusiasts.
Can I find long-stay holiday rentals in South Portland?
A long-stay holiday rental in South Portland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit South Portland for a holiday rental?
The best time to visit South Portland for a holiday rental is during the peak season from May to July. This period is especially popular among families and outdoor enthusiasts, as the warmer weather encourages an abundance of activities like hiking, cycling, and exploring the vibrant local arts scene. July, in particular, sees a lively option with numerous events and festivals, showcasing the best of what this charming city has to offer.

During these summer months, temperatures typically range from the mid-teens to low 20s Celsius, making it great for outdoor activities and sightseeing. You can enjoy strolls along the scenic waterfront, visit local parks, or indulge in the area's fantastic dining options. The pleasant climate enhances the experience, allowing for comfortable exploration of South Portland's unique attractions.

If you're looking for a more budget-friendly option, consider planning your visit in November. While this month is quieter, it offers a different kind of charm with fewer tourists and the opportunity to explore the city at a leisurely pace. This can be a great time to discover local shops and enjoy the peaceful atmosphere without the hustle and bustle of peak season.
Are there any remote work holiday rentals in South Portland?
In South Portland, there are ample options for remote work holiday rentals, with around 20 properties available in the area. Many of these rentals are equipped with essential amenities for working from home, including reliable Wi-Fi, dedicated desk spaces, and comfortable desk chairs, ensuring a productive environment for those needing to balance work and leisure.

The neighbourhoods around South Portland offer proximity to beautiful parks and waterfront areas, superb for taking breaks during the workday. The nearby Willamette Park is a lovely spot for a stroll or a picnic, while the vibrant streets of downtown Portland are just a short drive away, featuring a range of cafes and restaurants for a change of scenery. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a South Portland holiday rental?
Book your South Portland holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in South Portland, Oregon, United States of America?
In South Portland, visitors can enjoy a range of attractions that highlight the area's natural beauty and local culture. One of the main draws is the picturesque Willamette Park, which offers walking trails, picnic areas, and stunning views of the river. The park is ideal for outdoor activities like hiking and birdwatching, making it a favourite for nature enthusiasts.

Additionally, the South Portland Marina provides opportunities for boating and fishing, while the nearby Osprey Point offers scenic views and a peaceful atmosphere. The historic district of South Portland features charming local shops and eateries, offering a taste of the community's vibrant character. For those interested in art, the nearby Portland Museum of Art showcases a diverse range of exhibitions and collections, further enriching the cultural experience in the area.
Can I change or cancel my South Portland home rental booking on Vrbo?
To find South Portland holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the South Portland holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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