South Portland Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for South Portland vacation rentals

Beach nearby

Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (64 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is ￥32,573
￥66,477 total
includes taxes & fees
May 18 - May 19
Arlie`s Digs! - One Block To Willard Beach!
Smart TV

Willard Beach–Private Apt Near Portland & Parks

Willard Beach–Private Apt Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (5 reviews)
"Excellent in every way."
United States
Robert B.
The price is ￥15,893
￥39,125 total
includes taxes & fees
May 18 - May 19
Willard Beach–Private Apt Near Portland & Parks
Aerial view

South Portland Beach area rental

South Portland Beach area rental
Willard Beach
The price is ￥23,659
￥48,281 total
includes taxes & fees
May 21 - May 22
South Portland Beach area rental
TV

The Coastal Connection

The Coastal Connection
Thorton Heights
8.0 out of 10, Very Good, (1 review)
"Nice clean apartment very updated in older building. 3 Units or so in this renovated house. So expect to hear your neighbors. Also the main road has a lot of traffic at every hour. Semis shake the house. "
United States
Benjamin
The price is ￥14,572
￥47,893 total
includes taxes & fees
May 18 - May 19
The Coastal Connection
Interior

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (25 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is ￥19,295
￥36,431 total
includes taxes & fees
May 18 - May 19
Sunny Spot with Private Parking.
Interior

Modern Getaway by the Sea

Modern Getaway by the Sea
Ligonia
10.0 out of 10, Exceptional, (3 reviews)
"Enjoyed our girls weekend catching up and relaxing in this lovely space, with plenty of room and everything we needed! Host was very responsive. Would definitely stay again!"
United States
Kelley F.
Modern Getaway by the Sea
Outdoor dining

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (10 reviews)
"Great little place in south Portland! Close to many parks, lighthouses, and driving distance to downtown. Parking downtown and in the old port area can be tricky and expensive though. "
United States
Christopher R.
The price is ￥19,835
￥39,097 total
includes taxes & fees
May 18 - May 19
Peaceful & minutes from the Old Port with private parking
Exterior

Willard Square Family Home

Willard Square Family Home
Willard Beach
9.6 out of 10, Exceptional, (9 reviews)
"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"
United States
Steve S.
The price is ￥67,465
￥120,684 total
includes taxes & fees
May 18 - May 19
Willard Square Family Home
Smart TV, fireplace, books

Willard Beach: Cozy Apartment with a King Size Bed

Willard Beach: Cozy Apartment with a King Size Bed
Willard Beach
10.0 out of 10, Exceptional, (1 review)
"Lovely and quiet. Just what I had hoped for. "
United States
Heather R.
The price is ￥18,207
￥41,993 total
includes taxes & fees
May 18 - May 19
Willard Beach: Cozy Apartment with a King Size Bed
Exterior

Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is ￥60,092
￥65,500 total
includes taxes & fees
Jun 7 - Jun 8
Fortland Island Campground
Interior

Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location

Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location
Old Orchard Beach
10.0 out of 10, Exceptional, (33 reviews)
"Great location and great host. "
United States
Dwight P.
The price is ￥46,828
￥89,627 total
includes taxes & fees
May 24 - May 25
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location
Living area

Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (1 review)
"Beautiful new boutique hotel in Portland! Easy access to the Old Port and everything Portland has to offer. Very quiet, clean and well appointed rooms. The kitchen makes all the difference, even for a short stay! We loved our visit so much that we've booked a second trip!"
United States
Allison
The price is ￥38,711
￥66,006 total
includes taxes & fees
May 18 - May 19
Evalina Hotel
1 bedroom, desk, iron/ironing board, free WiFi

Charming West End Hideaway. Private Parking

Charming West End Hideaway. Private Parking
West End
10.0 out of 10, Exceptional, (51 reviews)
"Great stay in the heart of Portland, the bathtub was so good for a warming soak after a cool day of exploring the arts district! The host was very accommodating and we will be considering staying here again, for sure! "
United States
James S.
The price is ￥21,184
￥37,106 total
includes taxes & fees
May 18 - May 19
Charming West End Hideaway. Private Parking
Interior

Oceanfront Loft & Style | New Renovation

Oceanfront Loft & Style | New Renovation
Old Orchard Beach
The price is ￥20,230
￥59,598 total
includes taxes & fees
May 18 - May 19
Oceanfront Loft & Style | New Renovation
Outdoor dining

Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (41 reviews)
"Great home, great location, very accommodating, clear communication."
United States
Kristi H.
The price is ￥37,645
￥67,852 total
includes taxes & fees
May 18 - May 19
Modern & Sunny House Steps from the Promenade. Private Parking!
Exterior detail

Elegant condo - walk to Portland's best restaurants & Old Port

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.4 out of 10, Exceptional, (78 reviews)
"Lovely unit. Very comfortable bed. Nice to have off street parking. Walkable to Old Port. Would def stay again. "
United States
Erin H.
The price is ￥25,398
￥78,968 total
includes taxes & fees
May 19 - May 20
Elegant condo - walk to Portland's best restaurants & Old Port
House (1 Bedroom) | Interior

Couple's Glamping Getaway on Bonny Eagle Pond

Couple's Glamping Getaway on Bonny Eagle Pond
3.0 star property
Buxton
Couple's Glamping Getaway on Bonny Eagle Pond
Exterior

Charming two-bedroom, one-bathroom condo, two short blocks from the beach!

Charming two-bedroom, one-bathroom condo, two short blocks from the beach!
Old Orchard Beach
9.6 out of 10, Exceptional, (7 reviews)
"Great location!"
United States
Daniel
The price is ￥31,589
￥58,310 total
includes taxes & fees
May 18 - May 19
Charming two-bedroom, one-bathroom condo, two short blocks from the beach!
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (51 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
The price is ￥32,145
￥58,570 total
includes taxes & fees
May 27 - May 28
Full sized home
TV

Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.8 out of 10, Excellent, (6 reviews)
"This was a great place to stay. Easy to get to all of our destinations. Place was clean and comfortable. Would stay here again. "
United States
Ameleah B.
The price is ￥15,001
￥26,399 total
includes taxes & fees
May 19 - May 20
Private Entrance Residential Portland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top South Portland Hotel Reviews

Best Western Merry Manor Inn

Best Western Merry Manor Inn

10/10 Excellent
"This is a great hotel for families! The indoor and outdoor pool set up is amazing and the water temps were great! The hot tub in with a small pool is great for adults to relax while kids play! "
Theresa 1-night trip
Posted 1 hour ago
Best Western Merry Manor Inn

Find out more about South Portland

Search for holiday rentals in South Portland on Expedia! You can easily find your home rentals, villas, holiday apartments in South Portland using one of the methods below:

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  • Enter your travel dates to view the best deals on holiday rentals in South Portland while they last

Look no further and take a look at our great range of rental properties in South Portland!

Frequently asked questions

Can I find vacation rentals in South Portland?

Yes, you can find vacation rentals close to the most popular sights in South Portland, or you can choose a more secluded option if you'd like a relaxing place to stay. Tourists like the array of shops and top-notch restaurants in South Portland. Allow some time to check out the waterfront during your trip.

What are some of the best vacation home rentals in South Portland?

The Lookout by Bayley Vacation Rentals: Visitors like this South Portland vacation home rental. It is located by the ocean and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in South Portland?

With 29 Expedia vacation rentals, you're sure to find just the right place for your South Portland stay.

What can I see and do in South Portland?

Cultural attractions include Lyric Music Theater and South Portland Historical Society Museum, whereas Willard Beach and Casco Bay are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Maine Mall and Bug Light.

What are vacation rentals like in South Portland?

Vacation rentals are private properties you can reserve for several days or longer in South Portland. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.