Condo vacation rentals in Cumberland

Safe, convenient location close to all amenities

I love my Portland, Maine condo! It is comfy and relaxing on the inside .... fun and exciting on the outside. My home offers a unique blend of comfort and convenience. I enjoy having guests come and experience the unique city that I live in... you'll surely return. Well equipped full size kitchen / coffee bar A Portland Paradise, free driveway parking for two cars. A five minute ride into the exciting Old Port District or walk to neighborhood coffee shops, unique restaurants and local pubs.

Family · Value · Nearby

Charming 2-Bedroom Back Cove Retreat

Welcome to your perfect retreat in Portland! Discover the essence of Portland, Maine, at our enchanting getaway in Back Cove. Ideal for a long or short stay with your loved ones, our cozy space promises to be your home away from home. Just 8 minutes from downtown with off-street parking. Thoughtfully designed space with modern amenities. Family-friendly and pet-friendly (see "other details to note" regarding our pet policy). Proudly licensed with City of Portland License #: STHR-004018-2022.

Value · Family · Comfort

Cozy York - Spacious 2 Bedroom

This 2 bedroom condo is located on the first floor of our York street building. Just a few steps from Smalls cafe, The Danforth, Ruski's, & Cafe Ohno, this airbnb has all the in town walkability with the quiet neighborhood! Watch the sunrise over the waterfront bridge from the park benches or enjoy the cool evening breeze while listening to the tug boats. The two bedrooms are half-way below ground on the road side of the condo. The Piano does not work and is not in tune; it is decorative only.

Family · Value · Check-in

Direct Ocean View on the Eastern Promenade

This two bedroom, one bath unit is the perfect spot to enjoy all Portland has to offer. The bright and sunny open concept kitchen and dining area offer expansive ocean views for a relaxing stay. Enjoy the 88-acre Cutler Park to access boating, sun-bathing at the beach, sledding, trail walking, food trucks and more. Located within one mile of the Old Port and Arts District, the best of Portland is right around the corner. Walk to several neighborhood restaurants and coffee shops. Enjoy!

Family · Location · Indoor spaces

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

Family · Value · Air conditioning

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.

Family · Value · View

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!

Value · Family · Heating

Mary J. Eastburn House--Baxter Suite

City of Portland Reg. No. : STHR-002888-2021 Perched on a quiet street corner on Portland's Western Promenade, this historic residence enjoys what Longfellow called the "rarefied air of this little town by the sea," spectacular sunsets, and commanding views of the White Mountains. Built in 1891, the Mary J. Eastburn House now offers 3 private and exclusive guest suites for those who enjoy the grandeur of the past, updated with the luxuries and technology of the present.

Family · Value · Cleanliness

Luxury Beach Front Condo! Prime Location!

✨ Encourage reserving multiple nights to bring down the cost per night ✨ Single night available Oct 25 ✨ Minimum stay varies, typically 2 to 3 nights ✨ If you see a longer minimun, it’s likely to prevent the reservation from leaving a single night open. Just select different start date. ✨ Much appreciated if guests book trips connected to other guest trips ✨ Unless the trip is within the next few weeks, please don't book a trip that leaves a single night open ✨

Value · Family · Walkability

Waterfront Two Master Suite Penthouse with Rooftop

CO2024-01785 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.

Value · Family · Getting around

Downtown OOB Apt | Steps to Pier & Beach

Enjoy the best of both worlds! Tucked on the quieter side of the building, this peaceful 3rd-floor retreat offers a relaxing getaway with noticeably less train noise, all while keeping you just steps from the action. Walk to the beach, pier, local dining, Palace Playland, or hop on the trolley right outside. Includes free Wi-Fi, assigned parking, and easy check-in. The perfect spot to unwind!

Value · Location · Quiet

Top Of The Line Stay!

Modern Two Bedroom Gem, Relax in Style! Completely renovated two bedroom/one bathroom in East Deering. Beautifully appointed rental that features: hardwood/ceramic tile floors, granite, fully applianced kitchen, two queen size beds, washer/dryer in unit, porch, yard and a garage. Close to Old Port, Payson Park, Back Cove, neighborhood beach and Falmouth.

Family · Value · Sleep quality