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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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Superhost
A cozy sitting porch is adorned with two wicker chairs, featuring red and white striped cushions. A vibrant area rug displays an anchor pattern, while a large window allows natural light to enter and offers a view of the garden outside.
Condo in Portland

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.

4.82 out of 5 average rating, 125 reviews
Guest favorite
A cozy living area is highlighted by a vaulted ceiling with exposed wooden beams. A dark sofa is paired with a patterned rug, while a wooden coffee table sits in the center. Natural light enters through two window panes, and a small plant decorates a nearby shelf.
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

4.93 out of 5 average rating, 153 reviews
Top guest favorite
A bright living area is furnished with a light-colored sofa and cozy armchair. A wooden coffee table sits in front, complemented by a decorative plant. Two snowshoe decorations adorn the wall, while natural light filters through the windows with soft window treatments.
Condo in Portland

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.

4.98 out of 5 average rating, 99 reviews
Guest favorite
Condo in Wells

Starfish Condo Wells Beach

Enjoy the amazing sunrise as well as marsh and ocean views from this spacious just renovated one and a half bedroom condo with queen bed and queen Murphy bed. Fully equipped kitchen with granite counter tops and stainless steel appliances. Updated full bath with tub. Located within walking distance to many local area restaurants. After a fun filled day on the beach relax by the salt water pool or in the hot tub. Shared gas grill, picnic area, playground and basketball hoop. Parking for one car

4.9 out of 5 average rating, 117 reviews
Superhost
An open concept kitchen and dining area is visible, featuring a red retro fridge, white cabinetry, and a wooden dining table with black chairs. Natural light is provided by several windows, illuminating a minimalist decor style with a vase of flowers and a laptop on the table.
Condo in Brunswick

New 2BR 2King beds Private Apt Downtown Brunswick

Completely Newly Renovated 2 Bedroom Private Apartment Located 1 Minute Walk From Maine Street In Brunswick (Downtown). Great For Anyone Looking To Visit Or Explore Brunswick Including Bowdoin Parents, Potential Students, Vacationers. We have hard wood floor, granite counter top, open concept living room and kitchen, red retro fridge, and lots of windows lots of sunshine! Both bedrooms has a small closet and both beds are king sized with super comfortable memory foam mattress! Please Enjoy!

4.84 out of 5 average rating, 213 reviews
Top guest favorite
A spacious bedroom offers a large bed with a textured white blanket. Natural light fills the room through bright windows, highlighting a decorative plant in a pot. A small table at the foot of the bed is adorned with neatly arranged towels, while light-colored wood flooring adds warmth.
Condo in Portland

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

4.96 out of 5 average rating, 372 reviews
Top guest favorite
Condo in Old Orchard Beach

Luxury Beach Front Condo! Prime Location!

Special rate: Sept 9-11 ✨ 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 ✨

4.92 out of 5 average rating, 511 reviews
Top guest favorite
The kitchen features modern stainless steel appliances, including a range and microwave. Granite countertops provide ample workspace, along with white cabinets for storage. A coffee maker and various utensils are neatly arranged, contributing to a functional and well-equipped cooking area.
Condo in Downtown Portland

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.

4.88 out of 5 average rating, 534 reviews
Top guest favorite
A cozy living area features a brown leather sofa and two woven armchairs flanking a wooden coffee table. Light flows in through two large windows with sheer curtains, creating a bright, inviting space. A decorative rug adds warmth to the floor.
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!

4.96 out of 5 average rating, 228 reviews
Top guest favorite
A bright and airy kitchenette is shown, featuring white cabinetry and modern appliances. A comfortable blue sofa sits in the living area, with a dining space for four highlighted by pendant lights. Large windows allow natural light to fill the room, enhancing the inviting ambiance.
Condo in West End

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.

5.0 out of 5 average rating, 148 reviews
Superhost
A bright living area features two dark leather sofas and a patterned area rug. Natural light enters through large windows adorned with sheer curtains. A coffee table is positioned in the center, and a piece of wall art enhances the space. A plant and floor lamp provide additional warmth.
Condo in Portland

Penthouse, Walk To The Old Port & The Beach!

The East End is Portland's favorite neighborhood! Walking distance to both the breweries and the best restaurants. This third (top) floor apartment has a small front deck and a nice shared courtyard tucked away in the middle of the city! Street parking is free in this part of the city. So park and explore the city on foot. From here you're a short walk to the Old Port, the East End beach & walking trails, the Observatory, and so much more! City #000826

4.93 out of 5 average rating, 150 reviews
Luxe
A modern living area is designed with large floor-to-ceiling windows that provide sweeping views of the marina and cityscape. A sleek black sectional sofa and matching ottoman are paired with a cozy armchair, accented by a striped red area rug on the hardwood floor.
Condo in Downtown Portland

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.

4.96 out of 5 average rating, 253 reviews

Popular amenities for Cumberland condo rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Weekly condo rentals

Guest favorite
A cozy living area features wooden beams and paneling, with a comfortable sofa and an ottoman. Natural light enters through the windows, highlighting decorative shelves and a compact kitchen area. A small table and lamp add functionality to the space.
Condo in Scarborough

Comfy condo with loft by the beach!

4.95 out of 5 average rating, 317 reviews
Top guest favorite
A serene view of a sandy beach at sunset, with soft clouds painted in hues of orange and pink against a clear sky. The sun sets gently on the horizon, reflecting on calm ocean waters, creating a tranquil atmosphere.
Condo in Old Orchard Beach

Oceanfront condo, spectacular views

4.84 out of 5 average rating, 122 reviews
Top guest favorite
A warm wooden interior features a cozy seating area with a light-colored couch and decorative pillows. Floating shelves display various items, and the kitchen is visible in the background, showcasing essential appliances and a stylish design. Natural light filters through a skylight above.
Condo in Scarborough

Cozy condo by the beach!

4.96 out of 5 average rating, 432 reviews
Guest favorite
An aerial view captures a seaside community, revealing sandy beach extending along the coastline. The calm blue waters contrast with the golden shore. Residential buildings line the streets, framed by natural greenery, indicating proximity to both the beach and local amenities.
Condo in Scarborough

Just Renovated! Pine Point Beach Studio Apartment

4.84 out of 5 average rating, 260 reviews
Top guest favorite
A living area features a sleek black chair and a wooden folding table positioned in front of a wall-mounted television. Light-colored walls are complemented by decorative wall art. A doorway leads towards the kitchen area, providing access to additional amenities.
Condo in York County

Tranquil Haven - Minutes from Perkins Cove

4.91 out of 5 average rating, 247 reviews
Superhost
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

4.77 out of 5 average rating, 295 reviews
Guest favorite
The entrance of the historical building is framed by lush greenery and colorful flowering plants. A brick pathway leads to a set of elegant steps, with decorative railings on either side. The front door, featuring a subtle arch, showcases a welcoming light blue hue.
Condo in Downtown Portland

Historic Condo in Downtown Portland Old Port

4.9 out of 5 average rating, 178 reviews
Top guest favorite
A bright living area is revealed, featuring large windows that allow natural light to fill the space. A cozy gray sofa and matching armchair are complemented by colorful pillows. A small side table holds a plant, and a soft area rug adds warmth to the hardwood floor.
Condo in Portland

Charming, newly remodeled space atop Munjoy Hill.

4.99 out of 5 average rating, 126 reviews

Pet-friendly condo rentals

Guest favorite
A decorative fireplace is centered against a light-colored wall, adorned with a framed vintage map above. A small statue and other items rest on the mantel. Natural light streams in from nearby windows, illuminating the wooden floor and a cozy green chair beside the fireplace.
Condo in Downtown Portland

Portland 1 Bedroom Condo in the Arts District.

4.93 out of 5 average rating, 206 reviews
Superhost
A wooden paddle displaying the word 'BEACH' is mounted on a porch railing. Lush green plants are seen cascading down from the railing, while colorful foliage can be seen in the background, contributing to a vibrant outdoor view.
Condo in Downtown Portland

Secluded Victorian Condo Downtown, Walk Everywhere

4.78 out of 5 average rating, 757 reviews
Guest favorite
Condo in Old Orchard Beach

Elegant 1 bedroom cabin just 50ft from the beach#2

4.79 out of 5 average rating, 168 reviews
Top guest favorite
A bright kitchen area features four wooden stools set at a white counter, illuminated by natural light from large windows. Soft yellow walls complement white cabinetry, with a granite countertop adding a touch of elegance to the space.
Condo in Damariscotta

River Escape - Studio Apt. with River Access

4.9 out of 5 average rating, 191 reviews
Guest favorite
The exterior of the cottage displays a warm wood façade with a porch adorned with potted flowers. Surrounding landscaping includes low shrubs and rocky features, contributing to a natural setting. A gravel pathway leads to the entrance, framed by greenery.
Condo in Edgecomb

A Spacious Vacation Cottage in Sheepscot Harbour

4.9 out of 5 average rating, 209 reviews
Top guest favorite
An open living space showcases a modern kitchen with a stainless steel refrigerator and a two-seater kitchen island featuring vibrant green bar stools. A comfortable gray sofa is adorned with decorative pillows and is positioned alongside a colorful area rug, all under soft, natural light.
Condo in Kennebunk

Over 1000 Five Star Reviews! Walk to Dock Square !

4.9 out of 5 average rating, 242 reviews
Top guest favorite
A well-equipped kitchen features modern appliances, including a stainless steel refrigerator and stove. A large island is complemented by bar stools, providing space for seating. The design includes ample storage and counter space, with a laundry unit concealed near the entrance.
Condo in Portland

My Old Port Sanctuary - Lux by the water & dining

5.0 out of 5 average rating, 86 reviews
Superhost
A cozy living area is presented with a spacious sectional sofa facing a wall-mounted television. Natural light filters through multiple windows, enhancing the open concept layout that connects to the adjacent dining and kitchen areas.
Condo in Portland

2025 Remodel, 5 Bedroom, 3.5 Bath, Parking, Deck!

4.64 out of 5 average rating, 364 reviews

Condo rentals with a pool

Guest favorite
A serene view of a calm river surrounded by lush greenery. Gentle slopes lead to sandy banks, while trees provide a natural border on either side. The water reflects the blue sky above, creating a peaceful ambiance ideal for outdoor relaxation.
Condo in Conway

Cozy Family Retreat with Saco River Access

4.91 out of 5 average rating, 149 reviews
Top guest favorite
The living area features a plush gray sofa and an armchair beside a large area rug. Natural light filters through a skylight, illuminating the space. A coffee table sits at the center, accompanied by two lamps and a faux fireplace, creating a cozy ambiance.
Condo in Ogunquit

Newly designed one-bedroom condo- heart of OGT

4.97 out of 5 average rating, 105 reviews
Guest favorite
A living room showcases a cozy seating area with two black sofas facing a television. A coffee table is centrally placed, adorned with a candle and a snack. A brick fireplace adds warmth, while natural light filters through the dual windows, dressed with light curtains.
Condo in Conway

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

4.96 out of 5 average rating, 132 reviews
Guest favorite
The kitchen features modern cabinetry with a light grey finish and granite countertops. Stainless steel appliances include a refrigerator, dishwasher, oven, and microwave. A window allows natural light to illuminate the space, and oak flooring runs throughout, providing a warm atmosphere.
Condo in Wells

Two-Bedroom Condo on the Wells/Ogunquit town-line

4.85 out of 5 average rating, 227 reviews
Top guest favorite
A modern kitchen is showcased with white cabinetry and granite countertops. Stainless steel appliances include a refrigerator, microwave, and dishwasher. Kitchenware is neatly arranged, enhancing the functional space. A light blue wall adds a calm touch, while a throw pillow with 'BEACH.' text provides a decorative element.
Condo in Wells

Steps to Wells Beach + Pool | Coastal Retreat

4.96 out of 5 average rating, 130 reviews
Top guest favorite
A charming two-story white house features a covered porch with railing and a central double-door entry. Lush greenery and colorful flower beds surround the property, enhancing the welcoming appearance. Large windows invite natural light, and the roof is adorned with shingles.
Condo in Kennebunkport

Luxury Coastal Retreat | Mins from Dock Square

4.99 out of 5 average rating, 67 reviews
Top guest favorite
An aerial view captures the condo community and its proximity to Old Orchard Beach. The clear blue ocean stretches in the background, with sandy shores visible. The surrounding area includes recreational facilities and parking, illustrating the convenient access to nearby attractions.
Condo in Old Orchard Beach

Condo in Old Orchard Beach

4.97 out of 5 average rating, 33 reviews
Guest favorite
A cozy living area is presented with two stylish armchairs and a matching sofa, all decorated with patterned cushions. A round coffee table sits in the center, resting on a textured area rug. Large windows allow for natural light and views of the ocean.
Condo in Old Orchard Beach

*GRAND VICTORIAN*MODERN *OCEAN VIEWS* 3 BEDRM

4.85 out of 5 average rating, 67 reviews

Destinations to explore