Condo holiday rentals in Cumberland County

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Popular amenities for Cumberland County condo rentals

Weekly condo rentals

Top Guest favourite
Condo in Portland
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 stars2 days 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 Portland
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 stars10 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 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!
Guest favourite
Condo in Old Orchard Beach
4.95 out of 5 average rating, 20 reviews

Cozy New Condo with Oceanview

JamesRating, 5 stars10 months ago
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.
Top Guest favourite
Condo in Portland
5 out of 5 average rating, 46 reviews

The Observatory Retreat

MarinaRating, 5 stars2 weeks ago
Excellent location with great restaurants & shops within walking distance, ample street parking, accommodating and friendly hosts, and a clean, bright space stocked with everything we needed for our long weekend in Portland!

Pet-friendly condo rentals

Top Guest favourite
Condo in Portland
5 out of 5 average rating, 41 reviews

My Old Port Sanctuary - Lux by the water & dining

CaseyRating, 5 stars3 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 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 stars2 days 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.
Superhost
Condo in Portland
4.83 out of 5 average rating, 29 reviews

Prime Location Old Port apartment

HillaryRating, 5 stars4 days ago
Amazing space right in the heart of Old Port!! Very satisfied! We’ll definitely be back!
Superhost
Condo in 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.
Guest favourite
Condo in Portland
4.9 out of 5 average rating, 92 reviews

Luxurious 2BR Penthouse | Ocean Views | East End

DaniRating, 5 stars1 week ago
This is a really beautiful apartment in a wonderful, dog friendly, walkable neighborhood. We loved the park at the Promenade which was busy, fun and bustling all times of day. There’s a small beach in walking distance as well as a food truck section of the park and kayak tours / rental. Old Port is about a 20 or so minute walk from here, but there are also a few very cool places to grab a bite and to shop that are walkable to this Munjoy Hill neighborhood. The bed is very comfortable and there’s tons of open closet space. The light at early morning and at sunset is just beautiful. I didn’t remember reading it in the listing but we did have to put down a security deposit and were notified about it one day before check in. I’m not sure if this is a Portland rental thing but we had never had to do that with an Airbnb before and I would have preferred a longer warning about it. Just a small red tape detail that changed the vibe a little. Otherwise, we loved it & really enjoyed our stay.
Superhost
Condo in Old Orchard Beach
4.84 out of 5 average rating, 91 reviews

Downtown Old Orchard beach 1 bedroom

SanjanaRating, 5 stars8 months ago
Amazing location. Very close to the beach. Perfect room! We enjoyed our stay at Mary’s place!
Superhost
Condo in Old Orchard Beach
4.75 out of 5 average rating, 106 reviews

Renovated quiet unit, pet friendly

TabethaRating, 5 stars8 months ago
We came during the off season and had a quick two day stay here and thought it was great for us and our two small dogs.

Condo rentals with a pool

Condo in Old Orchard Beach
4.78 out of 5 average rating, 9 reviews

30 second walk to Beach- Pool-Outdoor Shower

AleeshaRating, 5 stars11 months ago
place is perfect for my parents who are older and can easily get in and out of the condo. fellow people at the condo are nice and respectful.
Guest favourite
Condo in Old Orchard Beach
4.91 out of 5 average rating, 11 reviews

Grand Victorian Ocean Rentals Oob310

LisaRating, 5 stars10 months ago
Beautiful, spacious condo. Jenny was clear with all instructions. Location was central to things to do and right on the beach. It is a little pricey but worth it.
Top Guest favourite
Condo in Old Orchard Beach
5 out of 5 average rating, 15 reviews

LUXURY OCEANFRONT CONDO Best Location on the beach

JennyRating, 5 stars11 months ago
This place had everything we needed. The view was spectacular! We really enjoyed seeing fireworks from the deck. The home was very clean, kitchen fully stocked. We loved hearing live music each day and night. So much walkable fun for the kids. We had a wonderful stay!
Condo in Old Orchard Beach
4.81 out of 5 average rating, 48 reviews

*GRAND VICTORIAN*MODERN *OCEAN VIEWS* 3 BEDRM

CaseyRating, 5 stars9 months ago
Located right in the middle of all the action! Perfect beach access and my kids had a blast at palace playland. Unit had everything we needed.
Condo in Old Orchard Beach
5 out of 5 average rating, 4 reviews

Just steps to the beach

GingerRating, 5 stars9 months ago
This was exactly what we needed! What a perfect little place. It’s a 30-second walk to the beach and an easy 1.3 mile walk to the downtown area. We walked everywhere and clocked 15 miles per day between the beach stroll in the AM, scooter/jog with my kids to the arcade at 10am, and afternoon/evening walks to the nonstop carnival. The apartment has everything you need and the kitchen is so well stocked with the basics. Such a great place! Perfect for a family visit to the beach. Also, I was surprised by how clean and safe the downtown felt. Ideal for families and young kids. Thank you, Julie!
Superhost
Condo in Old Orchard Beach

Ocean View Studio Beach Condo

MargaretRating, 5 stars30 months ago
It was such a cozy, wonderful condo with ocean sounds and breezes right from the front door. Neighbors very kind and welcoming; never felt like a stranger from the first day! Although just a studio, quite spacious and very comfortable even when my husband and child came to visit! David always responded to any questions rather about the condo, condo building, or just a good place to eat! Just a lovely all around stay! All my classmates were jealous! :)
Condo in Old Orchard Beach
4.83 out of 5 average rating, 36 reviews

Maine, Beach front Condo! Vacation hotspot!

SydneyRating, 5 stars9 months ago
Lovely place! Fully stocked with everything you could ever need! King bed was extremely comfortable. Tammy was very friendly and responsive! Will definitely be back in the future!
Condo in Old Orchard Beach
4.82 out of 5 average rating, 11 reviews

Family Vacation Home walking distance to Beach

LaraRating, 5 stars22 months ago
This was our second year staying at Chandra’s place during our annual week in Maine and it was, once again, terrific. Quiet, clean and within walking distance to the beach and all Ocean Park/Old Orchard attractions. When the washing machine wasn’t working, Chandra was very responsive and immediately offered to cover our costs of using the laundromat (which she did at the end of the week). We would definitely go back again next year!

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