Condo vacation rentals in Cumberland

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Top-rated condo rentals in Cumberland

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Guest favourite

Condo in Kennebunk

4.89 out of 5 average rating, 202 reviews

Discover Dock Square…Walk Everywhere!

Free onsite parking for 1 car. Beautiful coastal décor and modern amenities makes this a perfect choice for your vacation. Walking distance to EVERYTHING! Dock Square is a 1 minutes walk. Music, Art and Fine Dining surrounds you. Lots of windows and a slider to the deck make this location bright and airy 2 private decks for your enjoyment, two bedrooms, 2 full bathrooms. Perfect for couples or families. Parking for one car in lot, added public park across s NO PARTIES Pets considered

Guest favourite

Condo in West End

4.94 out of 5 average rating, 111 reviews

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

Guest favourite

Condo in Old Orchard Beach

4.73 out of 5 average rating, 118 reviews

Attractive 1 bedroom cabin only 50 ft from beach#1

nestled in a restful pine grove just 50 feet from Maine’s finest beach. These 8 one & two bedroom charming Old Orchard Beach Cottages are decorated in a modern beach theme, providing guests with the modern conveniences of today. Conveniences include Smart TVs with Amazon Fire Sticks, Wi-Fi, individually controlled heat & air conditioning, fully equipped efficiency kitchenettes, & private baths. Ideal for group getaways! Enjoy the privacy of your own seaside cottage, oh, so close to the beach.

Superhost

Condo in Downtown Portland

4.9 out of 5 average rating, 131 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.

Superhost

Condo in Wells

4.77 out of 5 average rating, 123 reviews

Generic Two Bedroom - Stair access only

Our two-bedroom units are located on the first, second or third floor in our all-stair property. All of our two-bedroom units have two bedrooms, with a varying number of beds, two bathrooms, full kitchen, living room, dining room and patio/balcony. They have a washer and dryer too! All kitchens come equipped with standard dishes, baking and cooking supplies, as well as full size appliances! Best for larger families to spread out! Room requests are accepted but not guaranteed.

Superhost

Condo in Scarborough

4.77 out of 5 average rating, 261 reviews

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!

Guest favourite

Condo in Scarborough

4.96 out of 5 average rating, 344 reviews

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.

Guest favourite

Condo in Downtown Portland

4.96 out of 5 average rating, 191 reviews

"Cornelia" Penthouse Waterfront Suite

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.

Guest favourite

Condo in Scarborough

4.96 out of 5 average rating, 223 reviews

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.

Guest favourite

Condo in South Portland

4.95 out of 5 average rating, 164 reviews

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. Ideal 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!

Superhost

Condo in East End

4.88 out of 5 average rating, 105 reviews

East Bayside/ Munjoy - Charming Downtown Escape

Walking distance to restaurants, craft breweries, and historic sites, this East Bayside condo will make the ideal home base for next trip to downtown Portland. This condo offers three comfortable bedrooms, a well-equipped, full kitchen, and a cozy living area with wall mounted TV's for streaming your favorite shows. You'll find everything you need here for rainy afternoons or relaxing evenings following days out on the town.

Guest favourite

Condo in Old Orchard Beach

4.9 out of 5 average rating, 408 reviews

Luxury Beach Front Condo! Prime Location!

Unless the trip is within the next few weeks, we appreciate it if guests don't book trips that leave a single night open. Generally minimum night stay is 2 nights during the week and 3 nights over the weekend. 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!