Condo holiday rentals in Cumberland County

Elegant 1 bedroom cabin just 50ft from the beach#2

This beautiful cabin now features a new Queen size bed, a double futon in the living room & can accommodate up to 4 people. The cottage includes a fully equipped kitchenette with microwave, fridge, coffee maker, toaster, and dining area. Smart TV, WIFI. AC & Central heating. It also has a private full bath with tub/shower combo at this unique and tranquil getaway. Enjoy the privacy of your own seaside cottage close to the beach! BBQ grills and picnic tables with umbrellas dot the courtyard.

Oceanfront Condo with Awesome Views

Wake up to a full ocean view on a seven mile sandy beach! Enjoy this one bedroom condo's great views, private balcony, and fully furnished decorated living space, along with a full kitchen with dishwasher, and even including a washer and dryer! Walk to everything downtown Old Orchard Beach has to offer: Amusement park, restaurants, clubs, shopping, and the famous Pier. Downstairs is a bar/restaurant that features live bands seven days a week in summer. Enjoy the fireworks every Thursday!

First Floor Portland Condo 3 Bed 2 Bath + Parking

A cozy 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

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. Brand new kitchen and bathroom! Perfect 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!

Heart of city, water view, off street parking

Live like a local in this second floor haven in the heart of the city. 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. ****2nd floor walk up with no elevator

Modern Industrial Beach Cottage

Time for a beach vacation! Newly renovated studio apartment, right across the street from Pine Point! Stroll the seven miles of quiet, sandy, residential beach, or bring your bike for a quick ride to the Pier at Old Orchard Beach. Located nearby is a market and deli, restaurants, and a gift shop. Just 20 minutes drive to the heart of Portland, you won't want to miss the local breweries and shopping in Old Port. Kayak rental nearby. Be sure to check out our other listings!

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.

Waterfront Two Master Suite Penthouse with Rooftop

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 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.

Luxury Beach Front Condo! Prime Location!

Condo is directly on the beach! ✨Generally minimum night stay is 2 nights during the week and 3 nights over the weekend. Unless the trip is within the next few weeks, we appreciate it if guests don't book trips that leave a single night open. If you see a 14 day minimum, it’s only to prevent the reservation from leaving a single night open.✨ ✨To simplify things and to be fair to those that instant book, we typically do not negotiate rates. Thank you!✨