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Condo vacation rentals in Cumberland

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Top-rated condo rentals in Cumberland

Guests agree: these condos are highly rated for location, cleanliness, and more.

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Condo in Old Orchard Beach

4.72 out of 5 average rating, 114 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.

Condo in Downtown Portland

4.98 out of 5 average rating, 133 reviews

Sparkling Clean, Old Port 2 bed, water view

Perfect 5 Star rating for cleanliness, and described as 'sparklingly' clean by nearly all guests (even before COVID-19). Cozy, light-filled, recently renovated apartment in historic brick building with water views. A short walk to the Old Port, waterfront, Eastern Prom, and Eastern Prom Trail connecting East Beach to the Back Cove loop. Steps from the best restaurants in the city. There is not a better location for summer in Portland, and not a better apartment. 2 bedroom, 1.5 bathroom.

Condo in Portland

4.97 out of 5 average rating, 215 reviews

Cozy Portland Condo! 3 Bedroom + Free 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

Condo in Scarborough

4.96 out of 5 average rating, 337 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, full size sleeper sofa on ground level. 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.

Condo in Downtown Portland

4.86 out of 5 average rating, 348 reviews

Newly Renovated 10 Exchange Street Loft

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.

Condo in Downtown Portland

4.96 out of 5 average rating, 183 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 heated bathroom floors; 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.

Condo in Scarborough

4.78 out of 5 average rating, 236 reviews

Updated Studio Across From Beach!

Modern, newly renovated (2016) beach cottage with a funky industrial vibe. Located across the street from the beach, just about a 2 minute walk to reach the sand. Quick drive (15 miles) to Portland and walk or bike to Old Orchard Beach. Our unit is located across the street from the beach, making it the ideal location for your next beach vacation! Located 2 doors away from the local market and deli, grab a sandwich and head to the quiet local stretch of Pine Point beach.

Condo in Scarborough

4.96 out of 5 average rating, 214 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.

Condo in South Portland

4.95 out of 5 average rating, 160 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!

Condo in Downtown Portland

4.9 out of 5 average rating, 153 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 York County

4.89 out of 5 average rating, 207 reviews

Tranquil Haven - Minutes from Perkins Cove

Welcome to Tranquil Haven, your home away from home in the beach village of Ogunquit. I am hopeful that your time away will be relaxing, enjoyable, and an oasis away from the busyness of life This studio condo is minutes from Perkins Cove and the Marginal Way. It has been completely renovated with a relaxing feel and genuine coastal charm. Quiet and Peaceful with first floor conveniences and parking right outside the condo.

Condo in Old Orchard Beach

4.9 out of 5 average rating, 391 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!

Vacation rentals for every style

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Apartments

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A space thats all yours, with room for everyone

Popular amenities for Cumberland condo rentals

Free parking on premises

Air conditioning

Weekly condo rentals

Condo in Old Orchard Beach

4.71 out of 5 average rating, 193 reviews

Endless Direct Beachfront Views! 2 Oversized Decks

Condo in East End

4.99 out of 5 average rating, 96 reviews

Charming, newly remodeled space atop Munjoy Hill.

Condo in Downtown Portland

4.79 out of 5 average rating, 86 reviews

Bright 1-br in the heart of Portland!

Condo in Old Orchard Beach

4.88 out of 5 average rating, 33 reviews

Steps from the sandy beach! "Surf's Up"

Condo in Old Orchard Beach

4.94 out of 5 average rating, 70 reviews

Walk to beach, NO cleaning fee, Spotless Condo

Condo in Portland

4.98 out of 5 average rating, 47 reviews

Central Spacious 4 Bedroom, 5 Bed, 2 free parking

Condo in Old Orchard Beach

4.91 out of 5 average rating, 44 reviews

Boho Surf Studio: Steps from the Beach in OOB!

Condo in Old Orchard Beach

5 out of 5 average rating, 7 reviews

Charming Beachfront Stay with Patio & Character

Pet-friendly condo rentals

Condo in Downtown Portland

5 out of 5 average rating, 27 reviews

My Old Port Sanctuary! Lux by the water & dining

Condo in Downtown Portland

5 out of 5 average rating, 30 reviews

Romantic apt:West End +parking

Condo in South Portland

4.89 out of 5 average rating, 37 reviews

Ground floor 2 bed condo 1 block to Willard beach!

Condo in Falmouth

4.92 out of 5 average rating, 48 reviews

Falmouth 3 Bedroom/2 Bath Loft Condo

Condo in Portland

4.98 out of 5 average rating, 64 reviews

Charming 2-Bedroom Back Cove Retreat

Condo in Kennebunk

4.96 out of 5 average rating, 52 reviews

Newly Remodeled Coastal Getaway

Condo in Kennebunk

4.89 out of 5 average rating, 200 reviews

Discover Dock Square…Surfs Up!

Condo in Damariscotta

4.89 out of 5 average rating, 160 reviews

River Escape - Studio Apt. with River Access

Condo rentals with a pool

Condo in Wells

4.92 out of 5 average rating, 25 reviews

Family Friendly Condo | Nautical Mile Resort #111

Condo in Ogunquit

4.98 out of 5 average rating, 44 reviews

Lovely Seaglass Studio, Pool, Walk to Everything!

Condo in Wells

4.84 out of 5 average rating, 167 reviews

New Condo on the Wells/Ogunquit town-line

Condo in Wells

4.97 out of 5 average rating, 36 reviews

NEW Beachside Wells Beach Condo with Pool

Condo in Wells

4.91 out of 5 average rating, 87 reviews

Starfish Condo Wells Beach

Condo in Damariscotta

4.98 out of 5 average rating, 46 reviews

Lovely 2 bedroom riverside condo with pool

Condo in Wells

4.77 out of 5 average rating, 116 reviews

Two Bedroom Suite Condo

Condo in Conway

4.96 out of 5 average rating, 108 reviews

Cozy, clean, 2nd floor condo in Conway, NH!

Quick stats about condo rentals in Cumberland

Total rentals
30 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
2.6K reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi

Destinations to explore