Condo vacation rentals in Cumberland County

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Top-rated condo rentals in Cumberland County

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Guest favorite

Condo in Portland

4.98 out of 5 average rating, 114 reviews

Sparkling Clean, Old Port 2 bed, water view

Perfect 5 Star rating for cleanliness, and described as 'sparklingly' clean by nearly all guests (even before COVID-19). Cozy, light-filled, recently renovated apartment in historic brick building with water views. A short walk to the Old Port, waterfront, Eastern Prom, and Eastern Prom Trail connecting East Beach to the Back Cove loop. Steps from the best restaurants in the city. There is not a better location for summer in Portland, and not a better apartment. 2 bedroom, 1.5 bathroom.

Jun 14 – 21

ﺩ.ﺇ1,795 per night

Guest favorite

Condo in Portland

4.96 out of 5 average rating, 153 reviews

Peaceful Portland Condo! 3 Bedroom + Free Parking.

A peaceful getaway nestled in the Portland's Deering neighborhood. Enjoy the retreat that this beautiful light-filled condo has to offer, whilst being less than three miles from the Old Port! The space is bright, and open--filled with luxurious touches and local Maine art. With three bedrooms and two full bathrooms, there is plenty of space for a large group to stay. Also, enjoy three free parking spots during your stay. We can't wait to have you! 3.5 miles to Airport 3 miles to bus station

Oct 19 – 26

ﺩ.ﺇ1,748 per night

Guest favorite

Condo in Portland

4.91 out of 5 average rating, 136 reviews

Rustic Downtown Duplex with Private Deck

This condo is truly a unique & special space. Enjoy walking to the Portland Museum of Art, Merrill Auditorium, Arts District & the Old Port not to mention countless restaurants/bars/breweries just steps away. After a long day exploring come back to this relaxing two story rental & enjoy a beverage on your private deck. This condo is perfect for travelers that need extra space but don't want to sacrifice location. Bedrooms & Living space are on separate levels. Parking by request (small fee).

Jan 2 – 9

ﺩ.ﺇ2,155 per night

Guest favorite

Condo in Scarborough

4.96 out of 5 average rating, 279 reviews

Cozy condo by the beach!

Cozy condo across the street from Maine's beautiful Pine Point beach. Private entrance with one on-site parking spot. Queen bed in lofted area, full size sleeper sofa on ground level. Efficient kitchen area with fridge, stove, and microwave for preparing small meals. Wifi and TV equipped with a streaming device. Perfect place for one or two people who will spend most of their time enjoying our local trails, beaches, and restaurants before returning to this comfortable and quiet space.

Jan 3 – 10

ﺩ.ﺇ680 per night

Guest favorite

Condo in Portland

4.84 out of 5 average rating, 285 reviews

Newly Renovated 10 Exchange Street Loft

This renovated loft-style condo is right in the heart of the Old Port. Located on Portland's bustling Exchange Street, the loft is central to everything the Peninsula has to offer. Elevator access will take you from the apartment to the secure lobby. From there, shops, restaurants, night life and the working waterfront are just steps outside the door. Free off street parking is available for one car a few blocks away or a convenient pay-to-park garage is located next to the building.

Aug 15 – 22

ﺩ.ﺇ1,716 per night

Guest favorite

Condo in Portland

4.96 out of 5 average rating, 164 reviews

"Cornelia" Penthouse Waterfront Suite

2023 City of Portland Registration #20185280-ST Penthouse suite w/modern amenities, exposed beams and brick, poplar walls. Rooftop deck w/views of harbor and city. Separate master suites with custom showers and heated bathroom floors; one with soaking tub. Gas-fired Jotul stove in living room. Washer/dryer in unit. Easy elevator access. Spacious kitchen with granite countertops and wine cooler. Please note: animals (including assistance animals) not allowed due to owner's health.

Nov 13 – 20

ﺩ.ﺇ2,032 per night

Superhost

Condo in Portland

4.89 out of 5 average rating, 129 reviews

Pet-friendly brewery lovers dream w/fenced yard

Nestled in the historic East End, this remodeled condo is a stones throw away from Oxbow and minutes from Rising Tide and Austin Street Brewing. You’re just a 10min walk to the water and minutes from some of the best dining Portland has to offer! We welcome all furry friends and have free driveway parking on site with fenced in backyard and patio. PLEASE NOTE! The backyard is no longer grass and has been replaced with crushed stone. Short Term Rental License: STHR-003855-2021

Oct 29 – Nov 5

ﺩ.ﺇ999 per night

Superhost

Condo in Scarborough

4.76 out of 5 average rating, 207 reviews

Recently Updated Studio - Across from beach!

Modern, newly renovated (2016) beach cottage with a funky industrial vibe. Located across the street from the beach, just about a 2 minute walk to reach the sand. Quick drive (15 miles) to Portland and walk or bike to Old Orchard Beach. Our unit is located across the street from the beach, making it the ideal location for your next beach vacation! Located 2 doors away from the local market and deli, grab a sandwich and head to the quiet local stretch of Pine Point beach.

Oct 8 – 15

ﺩ.ﺇ542 per night

Guest favorite

Condo in Portland

5.0 out of 5 average rating, 106 reviews

Mary J. Eastburn House--Baxter Suite

Perched on a quiet street corner on Portland's historic Western Promenade, the Mary J. Eastburn House this season offers three private guest suites, two with kitchenette and living room, all with luxury bathroom and on-site parking. For those who enjoy the grandeur of the past, updated with the luxuries and technology of the present, and ready access to the splendors of the Maine coast, Longfellow's "little town by the sea" could be just the escape you're looking for.

Jun 10 – 17

ﺩ.ﺇ959 per night

Guest favorite

Condo in Scarborough

4.98 out of 5 average rating, 164 reviews

Comfy condo with loft by the beach!

Comfy condo with lofted bed across the street from Maine's beautiful Pine Point beach. Private entrance with one on-site parking spot. Queen bed in lofted area, efficient kitchen area with fridge and convection microwave for preparing snacks and small meals. Wifi and TV equipped with a streaming device. Perfect for one or two people comfortable sharing an intimate space after returning from a day exploring our local trails, beaches, and restaurants.

Dec 2 – 9

ﺩ.ﺇ756 per night

Guest favorite

Condo in South Portland

4.94 out of 5 average rating, 121 reviews

Rustic Willard Beach condo ten mins from Old Port!

Second-fl unit in historic 150-yr-old building one block from South Portland's premiere beach! Minutes away from historic Portland Head Light and Downtown Portland. Quaint, spacious and tucked away in charming Willard Square. Ideal for families, friends, or couples looking for a relaxing coastal retreat. World-famous Scratch Baking across the street, and the Old Port's incomparable restaurants, shopping and historic architecture across the Bay!

Feb 12 – 19

ﺩ.ﺇ1,097 per night

Guest favorite

Condo in Portland

4.91 out of 5 average rating, 243 reviews

Space, views, & a perfect location!

License Number: STHROOO3662018) Welcome to the East End! This third-floor, two-bedroom, one-bath condo sits atop Munjoy Hill. Leave your car in the driveway and walk or ride-share to everything; the Portland Observatory, Belvillve Bakery, Rosemont Market, a laundromat, and a Metro bus stop are just around the corner. We are within a five minute walk of the Eastern Promenade or head downhill to the Brewery District, the Old Port, and Downtown.

Oct 12 – 19

ﺩ.ﺇ1,262 per night