South Portland Vacation Rentals

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Jul 29 - Jul 30
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Aug 1 - Aug 3
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Aug 8 - Aug 10

Vacation Rentals in South Portland

The Weldon Hotel
Relax in a spacious living area with a sofa, dining table, and flat-screen TV.

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (68)
"Absolutely beautiful place to stay. "
$496 nightly
The price is $534
Aug 14 - Aug 15
Total includes taxes and fees
The Weldon Hotel
68 East Grand Ave
Enjoy cooking in this well-equipped kitchen with stainless steel appliances, a marble countertop, and a sink.

68 East Grand Ave

3.0 star property
8.0 out of 10, Very Good, (4)
"nice place close to all"
68 East Grand Ave
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Enjoy a scenic ocean view from the comfort of your room, with a deck perfect for relaxation or dining.

Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

9.8 out of 10, Exceptional, (213)
"We stayed off season to just get away. The beach view is really nice. We went to the restaurant downstairs for food and live music. Very convenient! Place was clean. "
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Studio Unit Walkable Everywhere
1 bedroom, bed sheets

Studio Unit Walkable Everywhere

$206 nightly
The price is $209
Aug 4 - Aug 5
Total includes taxes and fees
Studio Unit Walkable Everywhere
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
Relax in a comfortable bedroom with a plush sofa, decorative headboard, and a cozy rug.

Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was as described, clean, and in a quiet neighborhood. Conveniently located to many local attractions. Check in and check out process was smooth. Overall enjoyed my stay very much. "
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Kitchen area with microwave, toaster, refrigerator, and sink.

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

9.8 out of 10, Exceptional, (50)
"We enjoyed ourselves very much! Close to everything we wanted to do. Would stay again."
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Gorgeous ocean-front home with stunning beach views
Guests can enjoy a leisurely day on the beach with access to sun loungers and umbrellas.

Gorgeous ocean-front home with stunning beach views

9.4 out of 10, Exceptional, (115)
"This property worked well for us. Ocean view was fantastic, beds were comfy, garage was handy for our car. Good in shoulder season, would like to come back and try it in the summer."
Gorgeous ocean-front home with stunning beach views
New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location
Fridge, microwave, oven, stovetop

New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location

9.2 out of 10, Wonderful, (5)
$284 nightly
The price is $309
Aug 5 - Aug 6
Total includes taxes and fees
New Listing! AmongstTheAspens - Off Grid Tiny House in a Serene Location
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
Relax in a serene beachside setting with an outdoor seating area featuring a round table and comfortable chairs.

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

9.6 out of 10, Exceptional, (62)
"Beautiful location even in the offseason, gorgeous house with plenty of room for guests. Very close to Portland for a nice dinner and some drinks. We also went and played some golf at summit in OOB and had a blast. Outdoor grill was perfect and overall we had a great time! Excellent host excellent location and perfect for what we needed. Would recommend highly."
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
Little Miss Cottages
Relax in a serene outdoor space with Adirondack chairs, a picnic table, and a fire pit.

Little Miss Cottages

2.5 star property
8.4 out of 10, Very Good, (86)
"Will be going back 😄"
Little Miss Cottages
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Smart TV

Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay there .the cottage was clean loved the charm of the place. Host was very helpful. Will return again. "
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
100 feet from the ocean 3 bedroom cottage 420 friendly
Walk along the boardwalk to the beach, flanked by rope barriers and a welcoming sign.

100 feet from the ocean 3 bedroom cottage 420 friendly

8.6 out of 10, Excellent, (18)
"Our family of 5 stayed here with our dog. This place has it all and we wanted for nothing. Stocked with towels, everything you would need in the kitchen. There’s even a washer and dryer on site. Right next the beach and a short walk to the pier. It was very clean and well taken care of. We will definitely be back!"
100 feet from the ocean 3 bedroom cottage 420 friendly
Rustic-Modern Barn Retreat Near OOB Beach & Pier
Enjoy cooking in this well-equipped kitchen with a central island and stainless steel appliances.

Rustic-Modern Barn Retreat Near OOB Beach & Pier

10.0 out of 10, Exceptional, (1)
"Place was great. We had some issues with tv but host was helpful and super responsive! The small one in bedroom never worked but I didn’t reach back out for help as we didn’t need it. Walkable to OOB but little far without a wagon if you require lots of beach gear (we had surf and boogie boards so we just drive down which is fine.) Also, I thought there was a sleep sofa but it was a sofa with a chaise but we made it work for my son! I can’t say enough about the host, so accommodating and...
$516 nightly
The price is $563
Aug 24 - Aug 25
Total includes taxes and fees
Rustic-Modern Barn Retreat Near OOB Beach & Pier
2 bedroom cottage
Cozy living space with a kitchenette, sofa, dining table, and bench.

2 bedroom cottage

9.2 out of 10, Wonderful, (5)
"quiet, clean, short walk to beach"
2 bedroom cottage
Bright and airy condo with beachfront access and walkable entertainment nearby
Fridge, microwave, oven, stovetop

Bright and airy condo with beachfront access and walkable entertainment nearby

8.0 out of 10, Very Good, (1)
"Not a bad spot. Just don't expect too much in the way of frills and be prepared to be flexible with sleeping/parking arrangements."
Bright and airy condo with beachfront access and walkable entertainment nearby
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location
Enjoy the ocean view from this spacious balcony with a table and two chairs.

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

10.0 out of 10, Exceptional, (14)
"Stunning property and great location! "
$860 nightly
The price is $937
Aug 17 - Aug 18
Total includes taxes and fees
Ocean Front Penthouse suite, Luxurious 2-bedroom,1350 sqft,2 decks, A++ location
4-bedroom vacation home steps to Old Orchard Beach Pier
Stroll along the pier, taking in the serene views of the ocean and surrounding landscape.

4-bedroom vacation home steps to Old Orchard Beach Pier

9.8 out of 10, Exceptional, (10)
"Mitchells home was PERFECT.Always quick to communicate and very accommodating. If you are looking for a great place to stay I cant say enough good things. Well stocked he has thought of everything people need when away. He even has games to play which was a nice surprise. You wont regret staying bere! Thanks again so much Mitchell!!!"
4-bedroom vacation home steps to Old Orchard Beach Pier
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !
Enjoy the ocean view from this deck with a comfortable seating area featuring wicker furniture and a small table.

Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

10.0 out of 10, Exceptional, (36)
"The view is beautiful and has everything you need "
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !
Idyllic 3 Bed/2Bath condo in Old Orchard Beach, steps to the beach
Beach

Idyllic 3 Bed/2Bath condo in Old Orchard Beach, steps to the beach

8.0 out of 10, Very Good, (3)
"Loved how close it was to everything,could be a little more updated on a couple of things"
Idyllic 3 Bed/2Bath condo in Old Orchard Beach, steps to the beach
Private Entrance Residential Portland
Kitchen area with stove, refrigerator, sink, and wooden cabinetry.

Private Entrance Residential Portland

8.0 out of 10, Very Good, (1)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
$175 nightly
The price is $177
Jul 30 - Jul 31
Total includes taxes and fees
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

Clarion Hotel Portland

Clarion Hotel Portland

10/10 Excellent
"Nice place"
Ray 1-night trip
Posted 22 hours ago
Clarion Hotel 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?

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach: You might want to consider this vacation home rental near South Portland, which offers a garden, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in South Portland?

With 56 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.