Condo vacation rentals in Portland

4.94 out of 5 average rating, 112 reviews

The open-concept living space showcases exposed brick walls, vaulted ceilings, and natural light from overhead skylights. A kitchen with stainless appliances and wood cabinetry is paired with a dining table and sleek chairs, while a television is mounted on the wall, enhancing the modern feel.

Condo in West End

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

The exterior of a restaurant features a bold sign reading 'OTTO' above a large glass window showcasing the interior. A black awning extends over the entrance, while adjacent stores are visible along a brick-paved sidewalk, creating an inviting street scene.

4.9 out of 5 average rating, 134 reviews

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.

Condo in Old Orchard Beach

4.9 out of 5 average rating, 105 reviews

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!

The entrance of a modern building is highlighted by large glass doors framed in black. A secure access panel is visible beside the door, providing entry options. Stone detailing is present at the base, adding to the contemporary aesthetic.

4.86 out of 5 average rating, 397 reviews

Renovated Exchange St. Loft w/Free Parking

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.

4.95 out of 5 average rating, 177 reviews

A sandy beach extends along the calm blue waters, with gentle waves lapping at the shore. A lifeguard chair is positioned prominently on the sand, overlooking the waterfront and the distant lush greenery and buildings lining the coast.

Condo in South Portland

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!

4.77 out of 5 average rating, 268 reviews

A sandy pathway bordered by lush grass leads to a tranquil beach, with gentle waves reflecting soft colors of the sky at dusk. The horizon showcases a gradient of pastel shades, creating a serene landscape inviting relaxation.

Condo in Scarborough

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!

5 out of 5 average rating, 123 reviews

A well-equipped kitchenette is showcased, featuring modern cabinetry and a microwave positioned above a counter. A sink and coffee maker are visible, with a window revealing natural light through white blinds. Hardwood flooring completes the clean, inviting space.

Condo in West End

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.

Top guest favorite

An open-concept space is shown, featuring a modern kitchen with stainless steel appliances and a dining area with a table set for six. Large windows provide natural light and city views, while exposed wooden beams and sleek furnishings enhance the contemporary design.

4.97 out of 5 average rating, 206 reviews

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.

The entrance features a set of wide steps leading up to a double door framed by intricate architectural details. Large bay windows are visible on either side, complemented by greenery and potted flowers at the base, creating an inviting entryway.

4.91 out of 5 average rating, 159 reviews

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.

Condo in Old Orchard Beach

4.91 out of 5 average rating, 430 reviews

Luxury Beach Front Condo! Prime Location!

✨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!✨

A welcoming living area is framed by sloped ceilings and large windows, allowing natural light to fill the space. Comfortable sofas are arranged around a coffee table, while decorative plants add a touch of greenery. A mirror reflects the inviting atmosphere.

4.92 out of 5 average rating, 165 reviews

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!

Top guest favorite

A tree-lined street is seen, showcasing brick sidewalks and charming buildings of varied architecture. A black awning over a storefront adds contrast against the clear blue sky, while parked cars and outdoor seating hint at the vibrant atmosphere of the bustling downtown area.