Condo holiday rentals in South Portland

Luxury Beach Front Condo! Prime Location!

✨ Condo is directly on beach & in heart of Old Orchard Beach ✨ Special winter rates! ✨ Encourage reserving multiple nights to bring down the per night cost ✨ Minimum stay varies, typically 1 to 3 nights ✨ Unless the trip is within the next few weeks, please 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. Just select different start date. ✨ To simplify things we typically do not negotiate rates✨

Historic West End Condo 10 Minute Walk to Old Port

Our perfectly located condo in this brick federal building from 1848 is the ideal spot for your stay in Portland. Fully renovated and beyond comfortable. Walk to Old Port, Arts District or any restaurant/brewery you desire. Quite, top floor unit with self entry keypads and security cameras. Furnished and equipped with all the comforts of what you should expect and more. Interior offers lots of light, exposed brick, vaulted ceiling, stainless appliances, washer/dryer. Furniture is dialed in

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 summer fireworks every Thursday!

Luxury Condo in Downtown Portland Old Port

Luxury Condo in the heart of Portland's Old Port. Enjoy your stay on a beautiful historical street tucked away just steps from many restaurants, the art museum, state theater, and many other things downtown Portland has to offer! Well furnished and very clean. Every part of the rental is well utilized. Kitchen table can fold away when not in use, and features built in closets and cabinets. A true gem in the heart of the city, whether you are here to escape, explore, or on business.

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!

Cozy Two Bedroom on Munjoy Hill

This cozy first floor two bedroom apartment is close to everything the Portland Peninsula has to offer, making it easy to plan your visit. You will be steps away from the lively Washington Avenue neighborhood lined with shops and restaurants, and just a few blocks from the beautiful Eastern Promenade. A 10 minute walk takes you to the working waterfront Old Port area. A 5 minute walk takes you to several breweries in the East Bayside neighborhood. Portland STHR-002973-2021

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 is the only sleeping space. 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.

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.

Portland 1 Bedroom Condo in the Arts District.

You’ll love my sunny, clean home because of its central PENINSULA location in the heart of Portland's arts district with floor-to-ceiling windows on the first floor of a charming red brick Victorian. Walk to restaurants, music venues, theaters, museums, and galleries from this abode full of period details like high ceilings, wood floors, built-ins, decorative fireplace, and a full kitchen with all the basics. A truly unique space for a getaway.

Old Port on foot

Newly renovated, spacious and modern top-floor condo in a posh historic building in the heart of downtown Portland. Leave your car behind! Walking distance to tons of bars/restaurants, stores, a block from the Portland Harbor/Commercial St and 3 blocks from Merrill Auditorium. Please note there is an additional $50 cleaning charge for stays greater than 7 nights. For stays greater than 14 nights, the cleaning fee is $180.

Coastal Penthouse - Center of Downtown Portland!

Overlooking Portland’s historic downtown rests this coastal penthouse located on the most vibrant street in the city! This one-bedroom apartment is fitted out with all of the amenities needed for a Maine vacation! Enjoy relaxing in luxury while only feet away from Portland’s most popular destinations. This penthouse is perfect for those here for business or a Maine getaway!