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

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, 110 reviews

Popular with guests booking holiday rentals in Portland

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 97 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 9.5
Exceptional - What previous guests thought, 64 reviews

Popular with guests booking holiday rentals in Portland

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 155 reviews

Popular with guests booking holiday rentals in Portland

Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 48 reviews

Popular with guests booking holiday rentals in Portland

Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 10 reviews

Popular with guests booking holiday rentals in Portland

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 77 reviews

Popular with guests booking holiday rentals in Portland

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

Popular with guests booking holiday rentals in Portland

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Enjoy breakfast in South Portland and nearby

West End Inn

Portland
Breakfast options
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 77 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
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 97 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$195.11 per night
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 48 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 8.1
Very good - What previous guests thought, 10 reviews

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

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.

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.

Scored out of 10, guest rating 7.7
Good - What previous guests thought, 14 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
Breakfast options
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

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

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

The Docent's Collection

Portland
Free cancellation options available
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 110 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$201.81 per night

East End Annex

Portland
Free cancellation options available
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.

Island View House BnB Self Check-In

Portland
Free cancellation options available
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 153 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.

A Foodie s Delight

Portland
Free cancellation options available
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

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.

Back Cove Views

Portland
Free cancellation options available
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 13 reviews

Back Cove Views in Portland features accommodation with free WiFi, 1.5 km from East End Beach, 25 km from Funtown Splashtown USA and 400 metres from Portland Observatory.

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$692.15 per night

Highly rated holiday rentals in South Portland and nearby

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 64 reviews

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

From US$366.40 per night

Best Bower

Portland
8.0+ review score
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 155 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.