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Vacation rentals with beach access in Chebeague Island

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Popular amenities for Chebeague Island beach access rentals

Apartment rentals with beach access

Top guest favorite
A brightly lit living area features large windows draped with patterned curtains. A variety of plants bring life to the space, alongside a wooden coffee table and comfortable seating. The floor is covered with a colorful rug, adding warmth to the natural wood flooring.
Apartment in East End
4.97 out of 5 average rating, 510 reviews

Cozy East End 2 Bdrm. with Private Entrance

RebeccaRating, 5 stars2 weeks ago
We had an excellent stay at this property. The host was wonderful, providing us with plenty of local recommendations and always friendly. The house was easy to find and exactly as described in the listing. It was spacious with plenty of amenities and a well-stocked kitchen. The decor was upscale and tasteful. The only downside was some noise from people walking upstairs, as the house is quite old. The neighborhood was lovely and it was easy to get downtown via Uber. Overall, we highly recommend this property, especially for friends and couples.
Top guest favorite
The spacious living area features exposed wooden beams and wide pine floors, with natural light streaming through two windows. A decorative star is mounted on the wall above a mantel, while a cozy seating arrangement includes a patterned couch and rocking chair, inviting relaxation.
Apartment in York
4.98 out of 5 average rating, 309 reviews

History Steps from the Beach

SaulRating, 5 stars6 days ago
This is an historic home with nice modern touches to make it convenient and comfortable. Great location with a short walk to the beach. The house was very clean and cozy. Jean sent out a welcoming message with clear instructions on how to find the house, open the lockbox to get the house key, and how to log in to wifi. There are two stovetop burners, a fridge and plenty of utensils and plates for basic meal prep. Overall I enjoyed this place and would stay again.
Top guest favorite
A spacious living area features a large sectional sofa with colorful decorative pillows. A throw pillow with the phrase 'together' is positioned on the couch. Natural light is filtered through multiple window shades, and a ceiling fan offers additional air circulation.
Apartment in Old Orchard Beach
4.97 out of 5 average rating, 147 reviews

Welcome to Old Orchard Beach

KathrynRating, 5 stars3 days ago
This place was amazing, great location and so peaceful! I loved that I could walk to the beach and the Main Street. It was also nice that it was only a 20 min drive from the main city Portland
Guest favorite
An open-concept studio space features sloped ceilings and warm hardwood floors. A dining area includes a wooden table and chairs. A colorful floral armchair is positioned beside a television, which faces a spacious sleeping alcove with a queen bed covered in light bedding.
Apartment in South Portland
4.9 out of 5 average rating, 224 reviews

Willard Square - The View

GlendaRating, 5 stars1 week ago
My husband and I enjoyed staying at Glenn Mary Jane’s place. The bed was incredibly comfortable and the apartment had plenty of amenities. We enjoyed walking to the bakery across the street for breakfast and it was also a short walk to Willard Beach. The neighborhood was beautiful, peaceful and colorful. Overall the location was superb and Glenn Mary Jane was incredibly friendly and welcoming throughout our stay.
Superhost
A small dining area is set with a round table covered by a blue patterned cloth. Two wooden chairs are positioned around the table, which features a decorative item at the center. Natural light enters through two windows, accompanied by trailing green plants.
Apartment in Portland
4.8 out of 5 average rating, 266 reviews

Clean East Bayside Apartment- Amazing Location!!

EmilyRating, 5 stars1 week ago
The apartment was a perfect place for my friends and I to crash while we attended a concert in the area and hung around for an extra two days to explore! With 4 adult women, it was pretty cozy, but I thought the apartment was spotless, easy to find, and easy to access (and we got in late). Honestly, I’m not the heaviest sleeper, and I didn’t hear neighbors at all. I think one of my friends mentioned hearing the dog upstairs but didn’t find it disturbing. We moved the car both days and had to park the car either around the corner and then one street over—totally normal for this type of area. Plenty of great restaurants within walking distance.
Top guest favorite
A cozy living space features light blue walls and a sloped ceiling. A gray sofa is centered on a neutral area rug, with a wooden coffee table in front. Natural light floods in from a window above, providing a bright ambiance complemented by a floor lamp.
Apartment in York
4.97 out of 5 average rating, 153 reviews

Cute 1-Bedroom apartment in the woods by the sea

MeaghanRating, 5 stars6 days ago
Very sweet and well-appointed space. Check-in was easy and the stay was super pleasant and peaceful. Would definitely return!
Guest favorite
A waterfront scene features a memorial surrounded by green shrubbery, with the bay visible in the background. Two individuals are seen walking nearby, while the sky showcases a light blue hue with wispy clouds.
Apartment in East End
4.96 out of 5 average rating, 118 reviews

Charming apartment near ocean and fab restaurants

MichaelRating, 5 stars4 days ago
My wife and I stayed at Lisa's place for 3 days arriving very late on the first night. Lisa was very accommodating to our late arrival. The place was clean, very comfortable with a very well lit entrance, very safe for late night. The next day, we woke up and saw we were in a gorgeous area of the city and could walk to all the places we planned. Lisa had put together some information on local events for us and had sent us several links with information that we appreciated greatly. I could say a lot of things about the unit, but the best part was Lisa herself. This was the first time I had actually met a host and she was extremely friendly and engaging. I would stay here again or in any unit associated with Lisa.
Top guest favorite
A serene garden area is depicted, featuring a gently flowing stream bordered by smooth stones. Lush greenery and colorful flowers, including irises and daylilies, create a vibrant atmosphere. Stepping stones lead through the grass, inviting exploration of the tranquil landscape.
Apartment in East End
4.96 out of 5 average rating, 583 reviews

Peaceful Oasis on Munjoy Hill -2nd flr/3BR+parking

JulieRating, 5 stars1 week ago
Ani's place is AMAZING! The pictures don't do it justice actually. The apartment is far more spacious than it seems and it was decorated in a way that was very comfortable. There wasn't a bunch of unnecessary clutter, the beds were all comfy and the linens were spotless. This is a whole house that is comfortable and homey in the best kind of ways. The kitchen has everything you'll need and then some. Munjoy Hill is a fun area that is great for accessing downtown or the coast. There's a shop around the corner for anything you might have forgotten, coffee shops and restaurants within just a few blocks, and only a 20 minute walk to downtown. I love this area of Portland and Ani's place was sooooo much nicer than other places I've stayed. I'd highly encourage everyone to stay there.

House rentals with beach access

Top guest favorite
A charming waterfront cottage is presented with a bright blue door and two red chairs on a stone patio. Lush greenery surrounds the property, enhancing its inviting exterior. The tranquil waters of Pettingill Pond can be seen in the background, reflecting the sky.
Home in Windham
4.94 out of 5 average rating, 140 reviews

Waterfront Gem walkable to Restaurants!

LinhRating, 5 stars1 week ago
It’s very cute little house. We’re enjoy it. Thank you so much.
Guest favorite
Home in Wells
4.87 out of 5 average rating, 119 reviews

Drakes Island Beach Front Breathtaking Property !

PhilippeRating, 5 stars3 weeks ago
We had a wonderful stay at this beautiful beachfront home with our extended family, including a total of 6 adults and 5 kids. We had two additional adults spend one night, there was plenty of room for everyone. The house was spacious, comfortable, and perfectly suited for a group of our size. The location is unbeatable, right on Drakes Island Beach, with incredible views and direct access to the sand. While we didn’t go in the water, we spent plenty of time relaxing on the beach, walking along the shore, and enjoying the peaceful setting. The home was clean, well-maintained, and stocked with everything we needed. The large deck and open living spaces gave us plenty of room to spend time together and unwind. This was a perfect spot for a relaxing family getaway, and we’d absolutely return again. Highly recommended!
Guest favorite
A charming yellow cottage is surrounded by lush greenery, with a large front porch featuring two wicker chairs and a small table. Large windows invite natural light into the space, showcasing a welcoming exterior that blends with the tranquil landscape.
Home in Peaks Island
4.86 out of 5 average rating, 170 reviews

Booking Now: Year-Round Peaceful Island Getaway

CatherineRating, 5 stars1 week ago
Can’t say enough about how great our stay was! Andrew was incredibly responsive, let us check in early and check out late without even asking. It was a great location on the island, very walkable, even for my mother with a bad knee (she was exhausted after the first day though). Would absolutely stay again!! 10/10
Top guest favorite
The exterior of a 1840s farmhouse is shown, featuring beige siding with blue window shutters. The brick pathway leads to the side of the house, where utilities are visible. The surrounding area has greenery and a glimpse of neighboring structures.
Home in West End
4.97 out of 5 average rating, 123 reviews

2 bed house w/king bed, pets & off-street parking!

KellyRating, 5 stars5 days ago
Had a short but lovely stay here. Awesome location and Kathleen was very responsive and gave us great recommendations. Only wish we had planned to stay longer!
Guest favorite
An inviting living area features a comfortable sofa facing a large television mounted on the wall. A rustic trunk serves as a coffee table on a patterned area rug. Natural light enters through double doors with sheer curtains, adding warmth to the space.
Home in Downtown Portland
4.95 out of 5 average rating, 111 reviews

East End Unit

JamesRating, 5 stars2 weeks ago
My wife, myself and our pup loved our time at Christine’s. Thought it was a great value for the area and we appreciated how many little extras were included (snacks, beer, wine, seltzer, toiletries). Location is great for walks to East Prom or Old Port, and parking is a breeze with the dedicated driveway. It is a cozy fit if you’re a bigger person (I’m 6’ and I had just a few inches of clearance from the ceiling).
Guest favorite
A spacious kitchen and dining area features high wooden ceilings and large windows offering expansive views of the surrounding landscape. Light filters in through the windows, illuminating the dark granite countertops and wooden cabinetry. A dining table is set up nearby, creating an inviting space for meals.
Home in Bridgton
4.95 out of 5 average rating, 211 reviews

Dreamy Mountain Home w/ Hot Tub, Firepit, + Views!

AnnalisaRating, 5 stars1 week ago
Bellissimo soggiorno in luogo incantevole. la casa è calda, accogliente, spaziosa, bene arredata, con gusto e classe. La vista è meravigliosa. Siamo stati benissimo!!!
Guest favorite
The kitchen features modern white cabinetry and granite countertops. Stainless steel appliances include an oven, microwave, and refrigerator. Natural light enters through a window, enhancing the airy feel. Coffee maker and other essentials are readily accessible for guest use.
Home in Old Orchard Beach
4.95 out of 5 average rating, 164 reviews

New build with hot tub in Old Orchard Beach

RobRating, 5 stars3 weeks ago
An absolutely charming property that is close to the beach, the boardwalk and close to shops and restaurants. The property is very well designed for function, is very appealing and had a lot of features and the amenities that we were looking. Plus, the overall style was clean and appealing. The host is amazing and I highly recommend staying at this property. I will definitely go back.
Guest favorite
Home in Georgetown
4.96 out of 5 average rating, 23 reviews

Breathtaking Bay Views!

ColletteRating, 5 stars8 months ago
I can’t say enough about what a nicely appointed home in a beautiful setting this is. I came for peace and tranquility and it did not disappoint. I haven’t had such good sleep in over 2 years. Highly recommend and plan to return next year! Thank you all so much for sharing your lovely home.

Condo rentals with beach access

Guest favorite
A private balcony is showcased with comfortable outdoor seating and large potted plants. Vibrant flowers are visible in the background, enhancing the serene environment. The ocean can be seen in the distance, providing a calming coastal view.
Condo in Old Orchard Beach
4.91 out of 5 average rating, 430 reviews

Luxury Beach Front Condo! Prime Location!

DaisyRating, 5 stars1 week ago
Wonderful place, beautiful view, clean home, would Definitely rebooked in the near future! 100% recommend
Guest favorite
A sweeping view of a sandy beach stretches along the coastline, bordered by the ocean on one side. The horizon showcases a mix of blue sky and gentle clouds. A distant expanse of beach is visible, with sparse vegetation and occasional structures lining the shore.
Condo in Old Orchard Beach
4.9 out of 5 average rating, 105 reviews

Oceanfront Condo with Awesome Views

NadiaRating, 5 stars1 month ago
Je recommande à 100%
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
4.77 out of 5 average rating, 269 reviews

Modern Industrial Beach Cottage

Anne-SophieRating, 5 stars2 weeks ago
Très beau séjour! L’emplacement est parfait, tout ce dont on a besoin est sur place. Je recommande!
Guest favorite
An aerial view captures the coastal neighborhood near Pine Point beach, featuring a mix of single-family homes and green spaces. The landscape showcases a scenic expanse of beach, with roads lined by trees leading toward the water, highlighting the area's proximity to natural attractions.
Condo in Scarborough
4.96 out of 5 average rating, 350 reviews

Cozy condo by the beach!

JoshuaRating, 5 stars2 weeks ago
Wonderful little spot very close to the beach. Plenty of places to walk to from the location as well as a short drive to Old Orchard Beach. Would come back in a heartbeat!
Guest favorite
The exterior of a two-story building is shown, featuring multiple windows and a front porch adorned with potted plants. A well-maintained lawn surrounds the property, and trees provide shade along the yard. The pathway is bordered by manicured grass.
Condo in Portland
4.94 out of 5 average rating, 104 reviews

Top Of The Line Stay!

CelesteRating, 5 stars1 week ago
Great place to stay if you want to be close to downtown but with a larger, comfortable space. The place is exactly as described, exceptionally clean and tastefully decorated. No dollar store products here! The ground coffee and half and half really made it feel like we were staying at a friend’s home.
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
4.96 out of 5 average rating, 237 reviews

Comfy condo with loft by the beach!

BethRating, 5 stars3 weeks ago
This was a teeny tiny condo (<200 sq ft!) but spotlessly clean, well appropriated, and a great location. The bed was comfy and the loft area was tall enough to sit up and move around. It was a 5 minute walk to Pine Point Beach. There are about dozen other tiny cottages in the condo association, clustered around a central parking lot, so if all of them were full there wouldn’t be a ton of privacy but we were there in the off season and it was peaceful and quiet.
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
4.95 out of 5 average rating, 177 reviews

Rustic Willard Beach condo ten mins from Old Port!

HarryRating, 5 stars1 week ago
Amazing apartment at a great location! Lots of character and the newly renovated kitchen was a plus. Very quiet neighborhood that allowed us to relax. Dave is a great host and was very helpful and flexible when it came to our check in time. We definitely recommend his place and will be back soon! Thank you Dave!
Guest favorite
A serene harbor scene depicts several boats anchored in calm waters, surrounded by lush greenery and quaint buildings. The clear blue sky showcases white clouds, creating a peaceful coastal atmosphere.
Condo in York County
4.91 out of 5 average rating, 171 reviews

Cozy studio-5 minute walk to Perkins Cove!

JulienRating, 5 stars7 months ago
Great place to stay, Ogunquit is such an endearing place to be 😄

Quick stats about vacation rentals with beach access in Chebeague Island

  • Total rentals

    70 properties

  • Nightly prices starting at

    G$18,823 GYD before taxes and fees

  • Total number of reviews

    2.2K reviews

  • Family-friendly rentals

    60 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore