Condo vacation rentals in South Portland

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Popular amenities for South Portland condo rentals

Weekly condo rentals

Guest favorite
Condo in Pine Point
4.91 out of 5 average rating, 93 reviews

Beach Breeze

KimberlyRating, 5 stars8 months ago
Amy was very helpful and communicative and generous with an end of season late checkout. We were in town to celebrate my Dad’s 85th and she even offered to help with balloons! The place was perfect for us with my young nephews. The unit was well stocked with plenty of kitchen tools and cookware and dishes. There were plenty of linens and towels available to us. Very convenient to pine point beach. We would love to visit here again if it worked with our schedule.
Superhost
Condo in Old Orchard Beach
4.7 out of 5 average rating, 201 reviews

Endless Direct Beachfront Views! 2 Oversized Decks

KerryRating, 5 stars6 days ago
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!
Guest favorite
Condo in Old Orchard Beach
4.91 out of 5 average rating, 66 reviews

Rustic Retreat studio, steps to the Beach. Unit #3

KayleenRating, 5 stars7 months ago
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.
Guest favorite
Condo in East End
4.93 out of 5 average rating, 74 reviews

Fresh & Modern Family Friendly Central 2 bed

MadeleineRating, 5 stars1 week ago
Great apartment very centrally located in Portland - easy to walk everywhere, so close to great coffee shops and restaurants! Apartment was perfect for our family of four, and the pack and play and kid's toys were great! Very family friendly. Highly recommend!
Superhost
Condo in Old Orchard Beach
4.88 out of 5 average rating, 33 reviews

Steps from the sandy beach! "Surf's Up"

KatieRating, 5 stars9 months ago
We enjoyed our stay! The place was very clean. The hosts were responsive and helpful. The train does go right behind the place at an intersection. The horn is very loud, which was hard for our toddler. Just something to consider if you’re traveling with infants/toddlers. Overall, would definitely recommend!
Superhost
Condo in Downtown Portland
4.81 out of 5 average rating, 27 reviews

Prime Location Old Port apartment

VickiRating, 5 stars7 months ago
We had a lovely stay at Janis’s place. The location was amazing! Right in the quaint Old Port area and just a short block to the waterfront. The area has amazing restaurants and adorable boutiques. The condo is bigger than we expected, which was a nice plus. It had everything we needed and as super clean. Janis’s communication was superb. The beds were super comfortable, and having an elevator was great after a long day. As others have mentioned, the front bedroom can get a bit noisy, so lighter sleepers will want to choose the back bedroom. We had a wonderful time and we wouldn’t hesitate to stay here again!
Guest favorite
Condo in Portland
4.96 out of 5 average rating, 25 reviews

2-Bedroom Condo Close to Downtown

LinneaRating, 5 stars7 months ago
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.
Top guest favorite
Condo in Old Orchard Beach
4.94 out of 5 average rating, 70 reviews

Walk to beach, NO cleaning fee, Spotless Condo

HeatherRating, 5 stars7 months ago
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!

Pet-friendly condo rentals

Top guest favorite
Condo in East End
5 out of 5 average rating, 39 reviews

My Old Port Sanctuary - Lux by the water & dining

JasonRating, 5 stars3 weeks ago
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.
Guest favorite
Condo in West End
5 out of 5 average rating, 32 reviews

Romantic apt:West End +parking

RachelRating, 5 stars5 months ago
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.
Guest favorite
Condo in South Portland
4.92 out of 5 average rating, 53 reviews

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

HarrisonRating, 5 stars2 weeks ago
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.
Top guest favorite
Condo in Back Cove
4.99 out of 5 average rating, 69 reviews

Charming 2-Bedroom Back Cove Retreat

MelissaRating, 5 stars1 week ago
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!
Guest favorite
Condo in Kennebunk
4.89 out of 5 average rating, 211 reviews

Over 1000 Five Star Reviews! Walk to Dock Square !

BrittanyRating, 5 stars1 week ago
We had a wonderful stay over Memorial Day weekend! The location here truly can’t be beat-walking distance to everything Kennebunkport has to offer. We loved that the property was pet friendly and well stocked. The property itself was exactly as described with very comfy beds and a well stocked kitchen. We would absolutely stay here again. Robert and Janette were incredibly responsive with our questions and recommendations and had clear checking and checkout instructions. A true gem of a weekend getaway!
Superhost
Condo in Downtown Portland
4.9 out of 5 average rating, 51 reviews

Walk Everywhere | Free Parking | DogsOK | King Bed

MariahRating, 5 stars1 week ago
Nick’s and Kayla’s place was perfect for our little family getaway! Close to everything in a super walkable city. The space was just as described and came with a pack n play, booster seat, and stroller included, which made the trip a breeze. Clean and just the right amount of space for us and our two littles. Great for families! Thanks for a wonderful time!
Superhost
Condo in Brunswick
4.85 out of 5 average rating, 178 reviews

New 2BR 2King beds Private Apt Downtown Brunswick

HannahRating, 5 stars3 weeks ago
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!
Guest favorite
Condo in East End
4.9 out of 5 average rating, 92 reviews

Luxurious 2BR Penthouse | Ocean Views | East End

JustinRating, 5 stars2 weeks ago
Wonderful—everything about this place. I loved it and will stay again one day. Fantastic.

Condo rentals with a pool

Superhost
Condo in Ogunquit
4.74 out of 5 average rating, 19 reviews

Lovely 1 Bedroom condo with amazing ocean view

FrankRating, 5 stars10 months ago
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!
Top guest favorite
Condo in Wells
4.97 out of 5 average rating, 30 reviews

Cozy Beach Condo in Wells - Hot Tub & Pool!

EmilyRating, 5 stars1 week ago
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!!!
Guest favorite
Condo in Wells
4.85 out of 5 average rating, 187 reviews

Two-Bedroom Condo on the Wells/Ogunquit town-line

SusanRating, 5 stars2 days ago
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
Guest favorite
Condo in Ogunquit
4.98 out of 5 average rating, 45 reviews

Pretty Boutique Studio, Pools, Walk to Everything!

TaraRating, 5 stars7 months ago
Perfect for an extended weekend getaway! The condo was super clean and exactly as pictured! Hoping to stay here again in the future!
Guest favorite
Condo in Wells
4.91 out of 5 average rating, 91 reviews

Starfish Condo Wells Beach

WendyRating, 5 stars4 weeks ago
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
Superhost
Condo in Wells
4.71 out of 5 average rating, 7 reviews

Awesome get away spot in Wells!

ManuelaRating, 5 stars7 months ago
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.
Guest favorite
Condo in Wells
4.95 out of 5 average rating, 101 reviews

Coastal Condo with Pool at Wells Beach

MaryRating, 5 stars1 month ago
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.
Superhost
Condo in Wells
4.76 out of 5 average rating, 133 reviews

Generic Two Bedroom - Stair access only

CathyRating, 5 stars1 month ago
We enjoyed our stay at Village By the Sea. Located in the middle of the lovely town of Wells, Maine. The property was beautiful and very comfortable.

Quick stats about condo rentals in South Portland

  • Total rentals

    30 properties

  • Nightly prices starting at

    G$10,491 GYD 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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