Skip to main content

Holiday Rentals in South Portland

Find the holiday rentals that appeal to you the most

The best holiday rentals in South Portland

Check out our pick of great holiday rentals in South Portland

Filter by:

Review score

The Docent's Collection

Portland (Near South Portland)

Set within 24 km of Funtown Splashtown USA and 500 metres of Merrill Auditorium in Portland, The Docent's Collection features accommodation with seating area.

s
seth
From
United States
The apartment was fantastic. It's so big I couldn't find the third bedroom! Nicely appointed.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 104 reviews
Price from
US$212.61
1 night, 2 adults

The Brew House - 2nd Floor Private Apartment

Portland (Near South Portland)

Featuring air-conditioned accommodation with a patio, The Brew House - 2nd Floor Private Apartment is located in Portland.

S
Shauna
From
United Kingdom
Jeff is a wonderful host. The apartment was spotless and had everything you need for a great stay. It's a great space with a comfortable bed and lots of living space to relax. Around 15 mins walk to the old Port and lots of great eating and drinking spots within yards of the door. Jeff makes great beer too which is a bonus!
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 58 reviews
Price from
US$450
1 night, 2 adults

The Chadwick Bed and Breakfast

Portland (Near South Portland)

Located within 23 km of Funtown Splashtown USA and 2.5 km of Merrill Auditorium, The Chadwick Bed and Breakfast offers rooms with air conditioning and a private bathroom in Portland.

L
Laura
From
United Kingdom
Warm and welcoming staff. Great team, especially the three furry taste testers they employ. Great communications prior to our stay and upon self-check-in. The breakfast were varied and really tasty. The bed was really comfortable and meant two great nights sleep. If we find ourselves in Portland again we would only stay here. One of the friendliest, most homely places we’ve ever stayed in. Erin especially is like a long lost sister. Great job!!!
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 91 reviews
Price from
US$119
1 night, 2 adults

Island View House BnB Self Check-In

Portland (Near South Portland)

Located in Portland in the Maine region, with East End Beach and Portland Observatory nearby, Island View House BnB Self Check-In provides accommodation with free WiFi and free private parking.

S
Sarah
From
United Kingdom
Comfortable, well-appointed, spotlessly clean and good location.
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 149 reviews
Price from
US$450
1 night, 2 adults

East end. Walk to food, beer and downtown fun.

Portland (Near South Portland)

Set in Portland, 1.3 km from East End Beach and 25 km from Funtown Splashtown USA, East end. Walk to food, beer and downtown fun. Offers accommodation with free WiFi in a historic building.

L
Lawrence
From
United States
The apartment was very cozy. Separate bedrooms. In a neighborhood setting. Close to the old port and town. Close to the recreational trails. Clean. Fairly priced. Well equipped kitchen was great although I was not able to take advantage of it. Good to know for future return ... which I hope to do!
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 62 reviews
Price from
US$248.40
1 night, 2 adults

A Foodie s Delight

Portland (Near South Portland)

Situated in Portland, A Foodie s Delight features a restaurant, 1.5 km from East End Beach and 25 km from Funtown Splashtown USA.

A
Amanda
From
Australia
Great space, good to have washer/dryer, location was a bit rough but only 15mins walk to downtown.
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 9 reviews
Price from
US$370
1 night, 2 adults

Atlantic Ocean Suites

Old Orchard Beach (Near South Portland)

Featuring barbecue facilities, Atlantic Ocean Suites offers accommodation in Old Orchard Beach. Complimentary WiFi is featured.

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 50 reviews
Price from
US$224.40
1 night, 2 adults

Best Bower

Portland (Near South Portland)

Set 1.1 km from East End Beach, 26 km from Funtown Splashtown USA and a few steps from Portland Observatory, Best Bower offers accommodation located in Portland.

D
Diego
From
Spain
Very nice room in great location. The staff is really attentive, we could not have asked for a more comfortable stay.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 153 reviews

Bright Spacious Apartment - 2 BR 2 BA

Portland (Near South Portland)

Located in Portland, 1.5 km from East End Beach and 25 km from Funtown Splashtown USA, Bright Spacious Apartment - 2 BR 2 BA provides spacious air-conditioned accommodation with a balcony and free...

S
SJD75
From
United Arab Emirates
Spacious, very clean and very well furnished apartment. Its a pity we only stayed a night on our trip. It was just a 15 minute walk to Portland Harbor, and all the main restaurants. The hosts have also prepared a file with all the info you could need on restaurants, coffee shops etc, to ensure you don't need to look around much - very thoughtful.
Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 17 reviews

West End Inn

Portland (Near South Portland)

Situated in Portland, 22 km from Funtown Splashtown USA, West End Inn features air-conditioned rooms with free WiFi and express check-in and check-out.

D
Daniel
From
Italy
We had a lovely stay at this little Inn located in a beautiful area of Portland. The service has been amazing.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 76 reviews
All holiday rentals in South Portland

Most booked holiday rentals in South Portland and surroundings in the past month

See all

Popular with guests booking holiday rentals in Portland

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 105 reviews

Popular with guests booking holiday rentals in Portland

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 76 reviews

Popular with guests booking holiday rentals in Portland

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 62 reviews

Popular with guests booking holiday rentals in Portland

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 150 reviews

Popular with guests booking holiday rentals in Portland

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 91 reviews

Popular with guests booking holiday rentals in Portland

Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 50 reviews

Popular with guests booking holiday rentals in Portland

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 153 reviews

Popular with guests booking holiday rentals in Portland

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 59 reviews

Popular with guests booking holiday rentals in Portland

Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 17 reviews

Popular with guests booking holiday rentals in Portland

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 5 reviews

Highly rated holiday rentals in South Portland and nearby

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 105 reviews

Set within 24 km of Funtown Splashtown USA and 500 metres of Merrill Auditorium in Portland, The Docent's Collection features accommodation with seating area.

From US$245.37 per night
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 9 reviews

Situated in Portland, A Foodie s Delight features a restaurant, 1.5 km from East End Beach and 25 km from Funtown Splashtown USA.

From US$463.80 per night
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 59 reviews

Featuring air-conditioned accommodation with a patio, The Brew House - 2nd Floor Private Apartment is located in Portland.

From US$314.88 per night
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 50 reviews

Located 24 km from Funtown Splashtown USA and 4.4 km from Merrill Auditorium, Fleetwood House Bed and Breakfast in Portland provides air-conditioned accommodation with views of the garden and free...

From US$260.51 per night
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 10 reviews

Set in Portland, 24 km from Funtown Splashtown USA and 500 metres from Merrill Auditorium, Modern Walkable Old Port 2BR Loft offers air conditioning.

East End Annex

Portland
8.0+ review score
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 20 reviews

East End Annex has a terrace and is situated in Portland, within just 1.3 km of East End Beach and 200 metres of Portland Observatory. This holiday home features accommodation with a balcony.

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 150 reviews

Located in Portland in the Maine region, with East End Beach and Portland Observatory nearby, Island View House BnB Self Check-In provides accommodation with free WiFi and free private parking.

West End Inn

Portland
8.0+ review score
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 76 reviews

Situated in Portland, 22 km from Funtown Splashtown USA, West End Inn features air-conditioned rooms with free WiFi and express check-in and check-out.

From US$249.61 per night

These holiday rentals in South Portland and nearby have options with free cancellation

Spacious Portland Home Walk Downtown!

Portland
Free cancellation options available
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Located in Portland, 1.6 km from East End Beach and 24 km from Funtown Splashtown USA, Spacious Portland Home Walk Downtown! offers a bar and air conditioning.

Cumberland Casa - B

Portland
Free cancellation options available
Scored out of 10, guest rating 6.6
Pleasant - What previous guests thought, 8 reviews

Situated in Portland, 24 km from Funtown Splashtown USA and 1.2 km from Merrill Auditorium, Cumberland Casa - B features a restaurant.

Cumberland Casa - A

Portland
Free cancellation options available
Scored out of 10, guest rating 7.6
Good - What previous guests thought, 12 reviews

Located in Portland, 24 km from Funtown Splashtown USA and 1.2 km from Merrill Auditorium, Cumberland Casa - A provides a restaurant.

Crow's Nest

Portland
Free cancellation options available

Situated in Portland in the Maine region, with East End Beach and Portland Observatory nearby, Crow's Nest features accommodation with free private parking.

Pearl of Portland

Portland
Free cancellation options available
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 3 reviews

Set in Portland, 1.5 km from East End Beach and 25 km from Funtown Splashtown USA, Pearl of Portland offers a restaurant.

62 Views

Portland
Free cancellation options available

Situated in Portland and only 1.2 km from East End Beach, 62 Views features accommodation with sea views, free WiFi and free private parking.

Monument SWEET!

Portland
Free cancellation options available
Scored out of 10, guest rating 5.0
Passable - What previous guests thought, 1 review

Monument SWEET! is situated in Portland, 200 metres from Portland Observatory, 1.2 km from Merrill Auditorium, and 23 km from Aquaboggan Water Park.

From US$707.41 per night

Monument Garden SWEET

Portland
Free cancellation options available
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Featuring a garden and free WiFi, Monument Garden SWEET features accommodation attractively situated in Portland, within a short distance of East End Beach, Portland Observatory and Merrill Auditorium...

Enjoy breakfast in South Portland and nearby

Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 17 reviews

Located in Portland, 1.5 km from East End Beach and 25 km from Funtown Splashtown USA, Bright Spacious Apartment - 2 BR 2 BA provides spacious air-conditioned accommodation with a balcony and free...

From US$629.30 per night

Best Bower

Portland
Breakfast options
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 153 reviews

Set 1.1 km from East End Beach, 26 km from Funtown Splashtown USA and a few steps from Portland Observatory, Best Bower offers accommodation located in Portland.

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 62 reviews

Set in Portland, 1.3 km from East End Beach and 25 km from Funtown Splashtown USA, East end. Walk to food, beer and downtown fun. Offers accommodation with free WiFi in a historic building.

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 91 reviews

Located within 23 km of Funtown Splashtown USA and 2.5 km of Merrill Auditorium, The Chadwick Bed and Breakfast offers rooms with air conditioning and a private bathroom in Portland.

From US$227.81 per night
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 5 reviews

Situated in Portland in the Maine region, with East End Beach and Portland Observatory nearby, Historic East End - Top of Munjoy Hill! features accommodation with free WiFi and free private parking.