Holiday rentals in South Portland

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in South Portland

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Guest suite in Portland
Sunny West End Guest Suite with Harbor Views
Enjoy views of the working harbor from this bright, two floor guest suite in the historic West End. This garden oasis with stone walls and salt water pool (open seasonally) is walking distance to downtown. (Portland City Permit: 20185360-ST) Your safety is important to us! We are following strict guidelines for sanitizing all linens, towels, furniture, objects and surfaces. Airbnb has an incredibly thorough and helpful protocol! All doorknobs, light switches and hand-touched surfaces will also be alcohol sanitized for your arrival! Here is a link to the protocol we are following: https://www.airbnb.com/resources/hosting-homes/a/airbnbs-5-step-cleaning-process-explained-187. Please let us know if you have any questions! This guest suite is a private, two-floor space attached to our house. It has its own front and back entrances and is separated by locked doors upstairs and downstairs from the main part of the house. The suite is light and sunny and a wonderful place to rest. The downstairs sitting room has a table for two and built in seating for relaxing and enjoying the water views or watching tv. The bedroom and bathroom are upstairs with lovely views. You will given your unique code for the guest suite door which enables you to come and go on your own timing. Parking is always available in front of the house or within a block. Please note that parking is prohibited on our side of the street on Monday nights through Tuesday mornings the 2nd and 4th Monday of the month. You can park on the opposite side of the street. The guest suite is attached to our house, but with its own front and back entrances. The day before you arrive we will send you instructions about your arrival. There is a key code so you can enter on your own. We may see each other on the back deck or in the yard at the pool. We have two dogs and you might see them in the yard and also coming up the stairs to our back deck door. We are right next door if you need anything or have any questions, and are also very conscious of your privacy. Please feel free to reach out if you need anything. We love Portland! Just let us know if you would like advice on local hikes, beaches, entertainment or great food. Portland has incredible restaurants! Most within walking distance from the house. The house is in the historic West End neighborhood overlooking the working harbor of the Fore River. Within walking distance are Portland's Old Port and Arts Districts, as well as the Saturday Farmers' Market in Deering Oaks Park. Parking is very easy on the street in front of the house. You can drive to local spots like the beautiful lighthouse at Fort Williams in Cape Elizabeth or the beaches in Scarborough, but you can walk to downtown Portland in 15-20 minutes. It's great to visit Portland on foot. You can walk Danforth Street all the way down to the Old Port shopping area. Here are directions for a nice walk to the Old Port: Turn right on Danforth when leaving the house. Take your first left on Emery Street. At the four way stop, turn right on Spring Street. Take Spring Street for just over a mile. After passing Temple Street, take your first right onto Exchange Street. This is the heart of the Old Port. Have fun!! Please Note: All Guests agree to indemnify and hold the Property Owners harmless from any liability for personal injury or property damage sustained by Guest or parties invited onto the property by Guest.
24–29 MarIndividual Host,
€ 180 per night
4.99 out of 5 average rating, 264 reviews
Guest favourite
Flat in South Portland
Willard Square - The View
“So much bigger than in the photos.” A charming apartment in the Willard Beach neighborhood of South Portland, Maine. There are bakeries, ice-cream parlor and restaurants within walking distance. Easy access to Portland , Midcoast airport. The area has many local craft breweries and award winning restaurants. This apartment is the perfect spot to stay for your Maine vacation. It is a great walking neighborhood with many attractions nearby, but you might want a car for getting around the area. I
27 Jan – 3 FebIndividual Host,
€ 191 per night
4.89 out of 5 average rating, 199 reviews
Superhost
Flat in Portland
Spacious and Comfortable Private Apartment
Third floor (i.e. a few stairs) spacious apartment with a private entrance. Walking distance to Thompson’s Point, Maine Med and many other trails and attractions. The Old Port is a 5 minute drive (1.5 mi.). There is plenty of free street parking available. Space heaters warm the space in the winter, and a/c is provided in the summer. The house is shared by first floor tenants while our family occupies the second floor. Again, several stairs to navigate, but quite comfortable once you settle in!
31 Oct – 7 NovIndividual Host,
€ 88 per night
4.82 out of 5 average rating, 347 reviews

Popular amenities for South Portland holiday rentals

Stay near South Portland's top sights

The Maine Mall86 locals recommend
Portland International Jetport50 locals recommend
Fort Williams Park229 locals recommend
Thompson Point28 locals recommend
Portland Harbor Museum347 locals recommend
The Westin Portland Harborview4 locals recommend

Other great holiday rentals in South Portland

Guest favourite
Loft in South Portland
Serene studio apartment, close to everything.
16–23 AprIndividual Host,
€ 123 per night
5.0 out of 5 average rating, 105 reviews
Guest favourite
Apartment in South Portland
Rustic Willard Beach condo ten mins from Old Port!
12–19 JanIndividual Host,
€ 242 per night
4.94 out of 5 average rating, 116 reviews
Superhost
Flat in Portland
Self-check-in | Desk | Washer + Dryer | Kitchen 2
6–13 JanProfessional Host,
€ 90 per night
4.8 out of 5 average rating, 291 reviews
Guest favourite
Flat in South Portland
Beautifully renovated spacious 2br apt in SoPo💗💗💗💗
4–11 AugIndividual Host,
€ 274 per night
4.96 out of 5 average rating, 161 reviews
Guest favourite
Flat in Portland
Airy+Modern Studio + Portland's Historic West End!
12–19 NovProfessional Host,
€ 139 per night
4.88 out of 5 average rating, 287 reviews
Guest favourite
Flat in South Portland
Stylish Studio Apt with Parking
26 Jul – 2 AugProfessional Host,
€ 207 per night
4.95 out of 5 average rating, 255 reviews
Guest favourite
Flat in Portland
Compact & Complete in residential neighborhood
9–16 OctIndividual Host,
€ 164 per night
4.96 out of 5 average rating, 148 reviews
Guest favourite
Flat in Scarborough
Your beach retreat - eat, sleep, beach, repeat!
25 Apr – 2 MayProfessional Host,
€ 112 per night
4.83 out of 5 average rating, 609 reviews
Guest favourite
Guest house in Portland
The Carriage House at Libbytown
26 Jan – 2 FebIndividual Host,
€ 172 per night
4.97 out of 5 average rating, 562 reviews
Guest favourite
Cottage in Scarborough
Charming beach cottage
10–17 JanIndividual Host,
€ 115 per night
4.85 out of 5 average rating, 277 reviews
Guest favourite
Tiny home in Portland
The Garden Cabin Tiny Home
19–26 MayIndividual Host,
€ 148 per night
4.97 out of 5 average rating, 397 reviews
Guest favourite
Guest suite in Portland
Gorgeous Studio 2 Blocks from Eastern Prom!
31 Jan – 7 FebIndividual Host,
€ 111 per night
4.91 out of 5 average rating, 193 reviews

Quick stats about holiday rentals in South Portland

Total rentals

560 properties

Rentals with dedicated workspaces

290 properties have a dedicated workspace

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

160 properties allow pets

Family-friendly rentals

260 properties are a good fit for families

Total number of reviews

56K reviews

Destinations to explore