Condo holiday rentals in South Portland

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Popular amenities for South Portland condo rentals

Weekly condo rentals

Superhost
Condo in Old Orchard Beach
4.7 out of 5 average rating, 201 reviews

Endless Direct Beachfront Views! 2 Oversized Decks

KerryRating, 5 stars2 weeks 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!
Top Guest favourite
Condo in East End
4.99 out of 5 average rating, 96 reviews

Charming, newly remodeled space atop Munjoy Hill.

ChrisRating, 5 stars7 months ago
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)
Guest favourite
Condo in Old Orchard Beach
4.91 out of 5 average rating, 68 reviews

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

TylerRating, 5 stars1 day ago
The place was very easy to find, great location. Walking distance along the beach and sidewalk to attractions, great access to the beach. Very clean and well maintained place. The hosts are very responsive and polite with good recommendations of places to eat and things to do. Would definitely stay again!
Guest favourite
Condo in East End
4.93 out of 5 average rating, 74 reviews

Fresh & Modern Family Friendly Central 2 bed

MadeleineRating, 5 stars3 weeks 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!
Guest favourite
Condo in Old Orchard Beach
4.85 out of 5 average rating, 93 reviews

The Brunswick

ChantelRating, 5 stars3 weeks ago
Great place to stay! Convenient location above the Brunswick with panoramic views of the beach and ocean, and a short walk to bars, restaurants, shops, and amusements. The condo is clean, spacious and well furnished. The living room and the balcony have plenty of room to relax and enjoy the views and sound of the waves. The king mattress is super comfortable. The keyless entry pads to both the building and condo make it easy to get in and out without having to worry about keys.
Guest favourite
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.
Guest favourite
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 favourite
Condo in Downtown Portland
5 out of 5 average rating, 41 reviews

My Old Port Sanctuary - Lux by the water & dining

CaseyRating, 5 stars2 days ago
Shai’s place had everything we needed for a clean, comfortable stay! We loved the location and had plenty of space to relax inside the apartment with no noise from the street despite being so close to downtown. Highly recommend and would absolutely stay again if traveling to Portland.
Guest favourite
Condo in Downtown Portland
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 favourite
Condo in South Portland
4.93 out of 5 average rating, 54 reviews

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

JeffRating, 5 stars3 weeks ago
This is the second time staying at David's and it's even better than the first time. Very comfortable space in the best location. Look forward to coming back.
Top Guest favourite
Condo in Portland
4.99 out of 5 average rating, 70 reviews

Charming 2-Bedroom Back Cove Retreat

DonnaRating, 5 stars1 day ago
Julia’s place is super clean, well-appointed with everything you need in the kitchen and bath. The water pressure is excellent, the beds are comfortable and the other tenants in the house were very quiet & respectful. The unit is easy to find situated in a quiet, friendly neighborhood, perfect for walking the dog, running & cycling. It is within walking distance to Payton Park, the Back Cove Trail and good restaurants and an easy drive to the Eastern Promenade, downtown Portland & breweries. Julia, the host was very communicative & created a comfortable homey environment. Overall, we had a great 5-day stay and would highly recommend this hidden gem.
Guest favourite
Condo in Kennebunk
4.89 out of 5 average rating, 212 reviews

Over 1000 Five Star Reviews! Walk to Dock Square !

AnjaniRating, 5 stars1 week ago
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.
Superhost
Condo in Downtown Portland
4.9 out of 5 average rating, 52 reviews

Walk Everywhere | Free Parking | DogsOK | King Bed

CherylRating, 5 stars1 week ago
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.
Superhost
Condo in Brunswick
4.85 out of 5 average rating, 179 reviews

New 2BR 2King beds Private Apt Downtown Brunswick

HannahRating, 5 stars1 month 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 favourite
Condo in East End
4.9 out of 5 average rating, 92 reviews

Luxurious 2BR Penthouse | Ocean Views | East End

JustinRating, 5 stars3 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 favourite
Condo in Wells
4.97 out of 5 average rating, 31 reviews

Cozy Beach Condo in Wells - Hot Tub & Pool!

ChelseaRating, 5 stars1 day ago
Kathleen’s Airbnb has quite literally everything that you need. We have stayed in airbnbs before but none compare to the amenities she had. The welcome note and snacks was greatly appreciated! She was amazing with communication and had a binder at her Airbnb with reccomendations and rules which was very helpful. Definitely a great place to stay !
Superhost
Condo in Ogunquit
5 out of 5 average rating, 3 reviews

Ogunquit one bedroom walk to beach

MimiRating, 5 stars11 months ago
Great location and spacious one bedroom suite with hot tub! InnSeason Resorts is not in downtown Ogunquit but we walked there in about 20 minutes, which we didnt mind. Footbridge Beach is less than a 10 minute walk away. There are many restaurants, shops and markets close by mostly by car but also two restaurants right next to the resort! I didn’t expect such a spacious place. The bedroom is large with a king size bed and ensuite hot tub and sink (the bathroom has its own sink as well). The kitchen has everything one can possibly need with a one burner portable stove. Katy was super responsive and helpful. The staff at the resort are also wonderful and accommadating. I highly recommend this for couples and parents with one or two kids!
Guest favourite
Condo in Wells
4.85 out of 5 average rating, 187 reviews

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

SusanRating, 5 stars1 week 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 favourite
Condo in Ogunquit
4.98 out of 5 average rating, 46 reviews

Pretty Boutique Studio, Pools, Walk to Everything!

MollyRating, 5 stars7 months ago
This was a great place to stay! My husband and I were very happy. Highly recommend!!
Guest favourite
Condo in Wells
4.91 out of 5 average rating, 92 reviews

Starfish Condo Wells Beach

WendyRating, 5 stars1 month 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
Guest favourite
Condo in Wells
4.95 out of 5 average rating, 101 reviews

Relaxing Beachside 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, 134 reviews

Generic Two Bedroom - Stair access only

DeysiRating, 5 stars3 weeks ago
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

    $83 NZD 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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