
Condo vacation rentals in South Portland
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Top-rated condo rentals in South Portland
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Popular amenities for South Portland condo rentals
Weekly condo rentals

My Old Port Sanctuary - Lux by the water & dining
Great location. Everything within walking distance. Very clean. Comfortable beds. Great water pressure in the shower. Well equipped kitchen. Feels like a very safe area and has a free parking spot. Would absolutely stay here again.

Endless Direct Beachfront Views! 2 Oversized Decks
Such a lovely stay! The view of the beach was absolutely beautiful, and the location was perfect—just a short walk to local stores and great restaurants. The space was very clean, cozy, and ideal for a mix of relaxing and fun weekend getaway. Highly recommend!

Charming, newly remodeled space atop Munjoy Hill.
Unit was very clean, situated in a quiet residential area and within walking distance to many of Portland's best bars, restaurants and attractions. Host was communicative and provided clear guidance on check-in/-out procedures and offered up suggestions to local attractions. On my recommended list - dinner at Twelve (one of the best restaurants in the US, IMHO); on-site food truck tacos washed down with a Hazy IPA at Bellflower or Austin Street Brewery; an everything bagel with lox & morning latte at Forage; the East Promenade for a food truck lunch, then a stroll along the waterfront trail to the port area for an ice cream cone at Gorgeous gelato; afternoon coffee at Double Great Coffee; and a post-dinner whiskey @ Independence Ice. Only downside on my visit was the upstairs neighbor. Dude clearly isn't a principal dancer in the Portland Ballet, as light on his feet wouldn't describe him. Not a stereo or TV issue - you can just hear the noise from him walking (8AM-10PM when there)

Rustic Retreat studio, steps to the Beach. Unit #3
Deborah was very helpful and quick to respond. She had great suggestions on where and what to visit. The travel magazines she had on her TV stand were extremely helpful. The bed was very soft, which I love, so I slept really well. We loved the touch of having beach chairs available. The only downsides I can think of, are that the shower is very small, and it’s hard to back out of the parking space.
Elegant, Stunning Condo with Sunny Patio
This condo really exceeded our expectations in how beautifully it was decorated and the amenities that it had. The location was perfect for walking down to the shops and restaurants in the Old Port area and Patrick and Tara gave a great list of restaurants and other places to check out close by. We were only there for 2 nights. I wish we could have stayed longer. Hopefully we will have a chance to stay again some time.

2-Bedroom Condo Close to Downtown
What a great location for a quiet stay in Portland! It’s 5 minutes by car to the Old Port and easily walkable/runnable to the Back Cove Trail and even to downtown Portland itself. The condo is lovely and just as described. My family (2 adults, 2 kids ages 3 and 7) was very comfortable during our 3-night stay. Lastly, Colin was responsive and a great host.

Walk to beach, NO cleaning fee, Spotless Condo
I went with a couple of friends for a relaxing weekend in the fall. It was lovely to have the beach so close by! We took a short day trip to Ogunquit where there was quite a bit of activity; lots of shops and restaurants to check out. Coming back to Melissa's place was cozy and relaxing. Since this was off-season, it is pretty quiet in the area. I felt more comfortable taking a stroll to the beach in the evening with a friend but would be hesitant to go alone. Despite that, we got the weekend we wanted: peace, relaxation, the ocean, things to do nearby, and a place to stay that was quiet, cozy, and clean. Thank you Melissa!

Cozy New Condo with Oceanview
Pattie and John were good hosts, and they always responded quickly to our questions and needs. The place is small but quaint and exactly as it looks in the pictures. The beach is beautiful, and is easy to walk to as are several stores, eating establishments, and amusements. Its a beautiful area that is very family friendly. Please note that at the end of the listing it says "active train tracks behind the building". People familiar with "OOB" would know about the trains, but we didn't. So, 20-30 feet behind the condo are the "active" tracks, and active means trains are coming throughout the day and night. When they pass the street crossing they always blow the horn several times in addition to the usual train noises, and it shakes the condo. Our hosts did offer us earplugs and a noise machine to help muffle the sound. Please take note of this if you're a light sleeper or have a baby. Overall we had a great week in "OOB", and John and Pattie's place is a great spot.
Pet-friendly condo rentals

Romantic apt:West End +parking
What a great little apartment! We stayed for three nights including Christmas and were delighted to find that the place had been decorated for the holiday. The bed is extremely comfortable, the shower has good water pressure. The location is perfect: a quiet street that is 10 - 15 minutes’ walk from the old port area and countless wonderful restaurants and shops. We loved that we could bring our dog and he also gave the place two paws up. We would certainly stay here again when visiting Portland.

Arlie's Digs! - One Block To Willard Beach!
Overall great experience, unfortunately the other folks that were supposed to join us weren’t able to, so it was just my girlfriend and I, which was still nice. A little chilly coming in the door, but hearing the place up was easy.

Charming 2-Bedroom Back Cove Retreat
This home was just perfect for a few days of R&R for my sister and me. The apartment is perfectly appointed with everything needed for a relaxing and easy stay. Kudos to the designer - the space was the perfect blend of a lovely aesthetic and function. I will certainly be remembering this little gem for the next time I'm in Portland!

Over 1000 Five Star Reviews! Walk to Dock Square !
Great location (definitely check out Pedro’s across the street). The place was clean and well stocked with necessities. Beds were comfortable, pillows were good, curtains would have been nice due to the early sunrises.

Walk Everywhere | Free Parking | DogsOK | King Bed
Nick and Kyla’s place was wonderful. It was perfect for our group. It looked exactly like the photos, and it was very clean. The location was perfect for getting around the Portland area with many things right in walking distance. Our hosts were very friendly and responsive, and their instructions were clear. I would definitely recommend staying with them to others.

New 2BR 2King beds Private Apt Downtown Brunswick
Great place to stay in Brunswick! Extremely walkable to the downtown restaurants and shops. Clean and bright space with spacious bedrooms (enough space to throw a pack-and-play in one of the bedrooms). Beds were comfortable and living room/kitchen good for socializing! Bonus — you can also access the Androscoggin River path for a nearby dose of nature and water. This is the second location of Spencer’s we’ve stayed in (the other about two years ago) and both stays were awesome. Highly recommend for a trip to Brunswick!

Luxurious 2BR Penthouse | Ocean Views | East End
Wonderful—everything about this place. I loved it and will stay again one day. Fantastic.

Downtown Old Orchard beach 1 bedroom
Amazing location. Very close to the beach. Perfect room! We enjoyed our stay at Mary’s place!
Condo rentals with a pool

Lovely 1 Bedroom condo with amazing ocean view
Marko was outstanding with responses and caring about our stay. The location is perfect.. walking distance to everything! And the VIEW was more beautiful than the photos!

Cozy Beach Condo in Wells - Hot Tub & Pool!
Kathleen’s Ogunquit Airbnb is perfect! She has thought of everything you may need and more. Kathleen was responsive when needed and communicated helpful details throughout our stay. The location is fantastic and made exploring the Maine coastline very convenient. Thank you, Kathleen!!!

Two-Bedroom Condo on the Wells/Ogunquit town-line
Christopher was a helpful host and his place was perfect! Clean, fully stocked, great location. It was close to lots of beaches and restaurants and the pool was great for the little ones

Pretty Boutique Studio, Pools, Walk to Everything!
This was a great place to stay! My husband and I were very happy. Highly recommend!!

Starfish Condo Wells Beach
This was a great find and enjoyed our 3 week there - We got to meet a few neighbors, and they were very nice as well - Very close to restaurants and Wells Beach - WIFI worked great as I work from home and the tip about leaving the second car at the Wells Transportation Center helped a lot ! Danielle was great with communication and rules - We would stay here again

Awesome get away spot in Wells!
Lovely cottage with EVERYTHING you need (e.g, kitchen & bath items are very well stocked with many options - condiments, coffee/tea, hair dryer, towels, health & beauty products - you name it!)! The location is close to lovely attractions and eateries. We visited Lobster Pt. Lighthouse and took a cliff walk - beautiful views! Ogunquit beach is also close by. Highly recommend Hobbs Harborside Restaurant - great seafood! Diane was a very accommodating and responsive host! It was the perfect location for our weekend getaway.

Relaxing Beachside Condo with Pool at Wells Beach
Julie’s place was very nice and very clean. The location was great, right across the street from the ocean. The kitchen was well-equipped and there was even a small basket of treats. Julie responded very quickly to any messages we sent. We would highly recommend this place.

Generic Two Bedroom - Stair access only
Great place to stay for our family of 4. I asked for 3 beds and that request was made possible. I enjoyed the area and it was quiet and peaceful place to rest after walking around the beaches and or state parks. Amenities were very good and communication with the check in team was excellent.
Quick stats about condo rentals in South Portland
Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ184 before taxes and fees
Total number of reviews
3.9K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- Long Beach
- Popham Beach State Park
- Surfside Beach
- Long Sands Beach
- Pemaquid Beach
- Brunswick Golf Club
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- Wentworth by the Sea Country Club
- East End Beach
- Palace Playland
- Ferry Beach
- Cliff House Beach
- Pemaquid Point Lighthouse
- King Pine Ski Area
- Purity Spring Resort
- Ogunquit Playhouse
- Dunegrass Golf Club
- Funtown Splashtown USA