Condo vacation rentals in Cumberland County

Fresh & Modern Family Friendly Central 2 bed

You will be close to everything when you stay at this centrally-located apartment. For the foodies and beer lovers, you are within a 10 minute walk to some of the best restaurants and micro breweries in the country. The entire architect design-owned building was recently completely renovated with a minimal & modern approach. Enjoy 2 spacious bedrooms, bathroom w/double vanity, & a kitchen designed for cooking meals to enjoy together at the dining table. Backyard grill, yard games & picnic table.

Cozy Two Bedroom on Munjoy Hill

This cozy first floor 2 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 strip lined with shops and restaurants, a few blocks from the beautiful Eastern Promenade with views, trails & parks, a 10 minute walk to the working waterfront Old Port area and a 10 minute walk to several breweries and shops in the East Bayside/Fox Street neighborhood. 2026 Portland STHR-002973-2021

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.

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!

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.

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.

Luxury Beach Front Condo! Prime Location!

✨ Encourage reserving multiple nights to bring down the cost per night ✨ 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 ✨

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.

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!

Walk to Top Dining • Boutique Stay • Parking

This beautifully renovated, light-filled apartment offers a rare mix of space, comfort, and walkability. Guests describe it as spotless, spacious, modern, and exactly as advertised—an easy, relaxing stay from booking to check-out. • 150+ five-star reviews • Guests return again and again • Dedicated parking spot • Everything you need for a seamless stay