Old Port holiday rentals

We found 163 holiday rentals — enter your dates for availability

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August 2025

September 2025

Discover a selection of 21 homes, 11 apartments and other holiday rentals in Old Port that are perfect for your trip. Holiday homes offer the amenities that you expect for your stay with friends, family or just your pet, such as Wi-Fi and a hot tub. Whatever you're looking for, you're sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Old Port

Showing deals for:31 Oct - 7 Nov

Living room with flat screen TV and desk overlooking North Street.

Exceptional

(17 reviews)

Beautiful NEW apt on top of Munjoy Hill with private deck and private parking.

Portland, ME

8% off

AU$405 per night

includes taxes & fees

Living Room has plenty of seating, tall windows overlooking the West End, and historic fireplace detail.

Exceptional

(8 reviews)

Historic Brick Apartment | Parking + Prime Location

Portland, ME

8% off

AU$866 per night

includes taxes & fees

Exceptional

(28 reviews)

Art Filled East End Home a short walk to waterfront, restaurants and shops

Portland, ME

9% off

AU$3,264 per night

includes taxes & fees

Exceptional

(158 reviews)

Chic 3 BR Retreat- Prime Old Port Spot with parking- Park and walk the town

Portland, ME

8% off

AU$939 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Old Port

Showing deals for: 31 Oct - 3 Nov

Private Rooftop Deck!/Artsy Apt/Old Port Arts Dist

Sleeps 4 · 1 bedroom · 1 bathroom

for 3 nights, 1 apartment

AU$711 per night

includes taxes & fees

Incredible Location! Heart of Old Port/Spacious Apartment

Sleeps 8 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 apartment

AU$1,543 per night

includes taxes & fees

Beautiful Unit in Serene Countryside Setting Near Wineries – Onsite Pool

Sleeps 4 · 1 bedroom · 1 bathroom

for 3 nights, 1 apartment

AU$504 per night

includes taxes & fees

Luxurious Penthouse with Modern Design in Downtown

Sleeps 5 · 2 bedrooms · 1 bathroom

for 3 nights, 1 home

AU$1,251 per night

includes taxes & fees

Old Port Penthouse Suite - Amazing Harbor Views

Sleeps 4 · 2 bedrooms · 2 bathrooms

for 3 nights, 1 apartment

AU$1,277 per night

includes taxes & fees

Top rated rentals - Old Port

Premier Host

Great base for a Portland stay.

This apartment was a very comfortable base for a stay in Portland. It was very clean and a great size for the two of us. We greatly appreciated the two large walk-in style robes that accommodated our large suitcases. The kitchen was well set up for those who might want to cook. I’d highly recommend this apartment to anyone considering a visit to Portland.

Mary M.

Stayed June 2023

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday home accommodation in Old Port?

Condos are the most popular kind of holiday home in Old Port, according to our data. Even if you've got something else in mind, Stayz has properties in loads of shapes and sizes. Take a look at our options to find your ideal fit.

How much does it cost to rent a holiday home in Old Port?

Several things influence how much you'll pay for a holiday home in Old Port, including the season, length of stay and type of property. But, all Stayz homes have something in common — excellent value. Simply enter your travel dates to find your home away from home.

How much does it cost to rent a beach house in Old Port?

The average price for a holiday home by the beach in Old Port will depend on when you're going and the type and size of property you want. You can quickly and easily find prices on Stayz by entering your destination and travel dates. Then use the filter tool to choose the number of bedrooms and amenities that you need, like WiFi, air conditioning and a pool.

Are there pet-friendly holiday homes in Old Port?

Good news. There are. You can choose from 13 holiday homes that roll out the welcome mat in Old Port on Stayz. Our cuddly best friends need to get away from it all too, so simply use our search function for pet-friendly holiday homes to find a perfect pad where Rover can be near his favourite humans.

What are popular home amenities in Old Port?

The most popular home amenities people are searching for in Old Port are a barbecue grill, an ocean view and a nearby waterfront. Whether you're on a trip with friends, family or even pets, Stayz holiday homes provide the best amenities for beginning new traditions with the people you cherish the most.

Are there large group holiday homes in Old Port?

Yes, you can pick from one of four holiday properties in Old Port that can host five or more people. From family reunions to events like a friend's birthday, these stays have ample room to kick back with your favourite people.

Are there holiday homes in Old Port that welcome kids?

Old Port has 13 family-friendly holiday homes to pick from. And securing a stay that welcomes little ones is easy with Stayz's "Properties good for families" filter. Besides having the entire place to yourselves, you'll also enjoy access to amenities and perks such as bunk beds, full kitchens and yards.

What are the top attractions for families in Old Port?

There are loads of wonderful things to do and see with the family in Old Port, including:

East End Beach
Sand Beach
Portland Observatory

Can I find two-bedroom holiday homes in Old Port?

Take off with your besties and experience complete comfort and privacy in one of the 10 two-bedroom holiday properties Old Port has to offer.

Are there holiday homes with WiFi in Old Port?

Pick from four holiday homes with WiFi in Old Port. If you'd like to disconnect from daily life on your trip, but still want to be connected to the internet, these properties have just what you need. Narrow your search by applying the WiFi filter on Stayz.

How can I find holiday homes with air conditioning in Old Port?

You can pick from 11 Stayz holiday homes with air conditioning in Old Port providing that gentle, cool breeze and extra touch of comfort. Enter your dates of travel and then take advantage of our filter tool to help you book stays with air conditioning.

How old do you have to be to rent a holiday home in Old Port?

You'll need to check with the Old Port holiday home you're looking at on Stayz as the minimum age varies. However, normally it's 16, 18 or 21.

How long can I rent a holiday home in Old Port for?

How long you can rent a holiday home in Old Port varies according to the property. Just enter your chosen travel dates to see a list of options offering extended stays. With a range of amenities like washing machines and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to find somewhere perfect to call your home away from home in Old Port.