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Kid-friendly holiday rentals in Chebeague Island

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Chebeague Island family-friendly rentals

Kid-friendly house rentals

Superhost
Home in Old Orchard Beach
4.72 out of 5 average rating, 18 reviews

By the Sea - sleeps 11! Walk to beach

HermannRating, 5 stars8 months ago
The accommodation is located in a quiet area and a short distance from the beach. I highly recommend this affordable place for a stay in Old Orchard Beach!
Superhost
Home in Old Orchard Beach
4.88 out of 5 average rating, 25 reviews

Walk to beach, shuffleboard, and bunk room

IsaacRating, 5 stars2 months ago
The place was great! It was just as described and Nina responds very quickly and was very sweet! We had a great time!
Top guest favourite
Home in Hallowell
4.98 out of 5 average rating, 122 reviews

Hilltop Retreat with Hot Tub & Sauna near Downtown

KarenRating, 5 stars4 days ago
We chose Jeff's house in Hallowell for our first trip to Maine because it is conveniently located near the Maine Cabin Masters' Kennebec Cabin Company store and Woodshed Restaurant, the town of Hallowell is quaint, and it's easy to get to Waterville, Cape Elizabeth, Portland, and Camden. We visited all of these places and were fortunate to have beautiful weather for late April. While we didn't use the hot tub and only tried the sauna once, we can definitely recommend this house for skiers. I can only imagine how good the sauna and the electric blankets on the comfortable beds would feel after a cold day on the slopes! Jeff is very friendly and provided recommendations. All around great visit and would stay again on our next trip to Maine.
Top guest favourite
Home in Intervale
4.97 out of 5 average rating, 179 reviews

Spacious 3 level family friendly home.Dog friendly

MatthewRating, 5 stars3 weeks ago
I went with my friends and it was fantastic! The surrounding area as beautiful and the added amenities really made the stay special for us.
Top guest favourite
Home in Kittery
4.98 out of 5 average rating, 287 reviews

Family Friendly 2BR 1 BA Coastal Kittery Home

ChristineRating, 5 stars1 week ago
I booked the house as a place for my family of 6 (4 adult children) and our black lab, to come together for Easter weekend. Since my boys live in Portsmouth we only needed 2 bedrooms and this house made the perfect getaway and place to host dinners. The house was spacious and very comfortable. We enjoyed the enormous fenced in yard all weekend. The host had many yard games which we played and our lab was so happy too. The fire pit was an added bonus for a night of s’more making. We truly had a wonderful time and the house really felt like home. Ps the stairs are fine once you get used to them. Rebecca was responsive and a wonderful host.
Top guest favourite
Home in South Portland
4.91 out of 5 average rating, 116 reviews

Cottage style home 2 blocks from the beach!

KatieRating, 5 stars6 months ago
We had a wonderful girl's trip staying in Diana's house! We walked to the beach and to Scratch bakery (twice). The house was perfect for the five of us with a great sitting area to hang out and chat. The house was clean and the instructions for cleaning up were easy to follow.
Superhost
Home in Freeport
4.84 out of 5 average rating, 55 reviews

Charming Historic Freeport House

KendraRating, 5 stars2 weeks ago
Spent the weekend here with friends and really appreciated the host’s hospitality! They accommodated an earlier check in, responded to messages promptly, and the space had comfortable beds and great linens. Would stay here again in a heartbeat!
Superhost
Home in Portland
4.89 out of 5 average rating, 151 reviews

Great Modern Space and House

MichelleRating, 5 stars4 months ago
We had an excellent stay at Mariella’s place. The cleanliness stood out to us and was much appreciated. Mariella was very accommodating and there for any questions or concerns. We felt right at home. Her home was in great location of a neighborhood for comfort and privacy while also be very convenient and a short ride to downtown Portland. I would recommend her home.

Family-friendly apartment rentals

Guest favourite
Flat in West End
4.91 out of 5 average rating, 560 reviews

Sophisticated Charm at an unbeatable price!

JonasRating, 5 stars2 days ago
The apartment was just as described by the host, and was very comfortable for a two night stay, for two couples. Excellent, proactive, communication by the host prior to check-in. Very clear instructions. The kitchen was well equipped for breakfast (which is the only meal we ate at the apartment during our stay). A serrated knife would be a nice addition. All of the appliances were very clean, and in good working order. Entry to the building was easy. Be comfortable climbing stairs. Five minute drive, or 15 minute walk to downtown. Quiet and peaceful neighborhood. Would definitely return, and recommended it to others. Thank you for a nice stay, Susan.
Guest favourite
Flat in Portland
4.91 out of 5 average rating, 114 reviews

Cheerful 2 Bedroom 2 Bath Garden Apt with Laundry

SusyRating, 5 stars1 week ago
Margaret’s place is very homey with all the necessities for a family gathering. The neighborhood is beautiful and close to beautiful trails
Superhost
Flat in East End
4.73 out of 5 average rating, 127 reviews

Ocean Way East End - 2

ChosieRating, 5 stars1 month ago
Super walkable and great for a weekend stay!
Top guest favourite
Flat in Belfast
4.89 out of 5 average rating, 200 reviews

Sunny apartment overlooks Main St.

Malka ReynaRating, 5 stars1 month ago
Great place to stay. Deck is nice and overlooks the water. Warm during cold weather. Host is kind and very helpful.
Superhost
Flat in Portland
4.86 out of 5 average rating, 856 reviews

Bright, Fun & Spacious Apartment on Back Cove

ErinRating, 5 stars1 month ago
Ian's place was great for a girls trip ti Portland. He was a great communicator if I had any questions or cleaning instructions. Will definitely stay again for any future trips to Portland.
Guest favourite
Flat in Portland
4.89 out of 5 average rating, 102 reviews

Portland Back Cove Hideaway-1 BR- With Patio

KristinRating, 5 stars4 months ago
I highly recommend staying here if you are visiting Portland! The apartment was adorable, very clean and in a perfect location. Alex had an entire list of recommendations that we found very helpful! We will definitely be back!
Top guest favourite
Flat in Kennebunk
4.99 out of 5 average rating, 111 reviews

Sunny, cozy 1 BR apartment

JenniferRating, 5 stars3 days ago
This apartment is simply perfect! I felt comfortable and safe and loved waking up to the beauty of the space, the kitchen has all new appliances and the colors and craftsmanship are impressive. There was plenty of room throughout and the bed is very comfortable. Thank you Rick! I would definitely stay at your apartment again. I also highly recommend this place because of the great, central location.
Top guest favourite
Flat in East End
4.97 out of 5 average rating, 456 reviews

Bright and cozy Munjoy Hill neighborhood apartment

RajRating, 5 stars2 weeks ago
Sadie and Laughlin are the best Airbnb hosts we have come across. We could not have asked for a better place to stay. The apartment is very clean, has lovely furnishings, is nicely decorated and had everything we needed for a very comfortable 3 and a half day stay in Portland. Both bedrooms are a good size and have incredibly comfortable beds. When we needed help with something, our hosts came around fast to help us. If we are ever back in Portland, we shall gladly book again with them. I would highly recommend this apartment!

Family-friendly apartment rentals

Guest favourite
Apartment in Wells
4.93 out of 5 average rating, 27 reviews

Family Friendly Condo | Nautical Mile Resort #111

LindaRating, 5 stars4 months ago
I had been staying here for 2 weeks and extended for another week. Again, just a great stay with very communicative hosts.
Guest favourite
Apartment in Old Orchard Beach
4.91 out of 5 average rating, 418 reviews

Luxury Beach Front Condo! Prime Location!

YurikaRating, 5 stars3 days ago
The place was beautiful and clean with a great balcony! Access to beach was so easy and so convenient. Thank you for hosting us !!
Guest favourite
Apartment in Old Orchard Beach
4.89 out of 5 average rating, 104 reviews

Oceanfront Condo with Awesome Views

CarolineRating, 5 stars1 month ago
This is the perfect place! Everything is very clean, and nothing missing! Kevin is very nice. He was good tips. I've always dreamed of coming to OOB in the winter and really enjoyed the experience! Loved our stay. With its location and double patios, the views are splendid! For lovers of the sound of the waves, the view of the sea, sunrises, long walks to the beach… this is the place!
Superhost
Apartment in Wells
4.75 out of 5 average rating, 126 reviews

Generic Two Bedroom - Stair access only

Rose-MarieRating, 5 stars2 months ago
The condo was very clean, tasteful decorated. Beds were comfortable. Loved the big table to play games and the living room was cozy for the evening and morning chats. Pretty views.
Top guest favourite
Apartment in Conway
4.96 out of 5 average rating, 110 reviews

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

RachelRating, 5 stars4 months ago
A beautiful condo, just 20 minutes away from the heart of North Conway. Everything was in pristine condition and it is always amazing to have a kitchen at our fingertips. Beautiful views of the woods out back. Would definitely recommend to those coming to visit the North Conway, New Hampshire area and surroundings!!!!
Superhost
Apartment in Newry
4.67 out of 5 average rating, 6 reviews

Np 2-102

Justin and LisaRating, 5 stars38 months ago
Great location between southridge and north peak express with a view of the southway trail that passes between buildings 1 and 2.
Guest favourite
Apartment in Conway
4.92 out of 5 average rating, 122 reviews

Cozy Family Retreat with Saco River Access

JeanineRating, 5 stars2 months ago
Our 3rd time staying here....great location and reasonably priced. Love the view out back to the trees and a peek of some mountains. Also great snow cleanup - we were here for a big storm and the plows cleared the car park and the paths were shoveled quickly.
Top guest favourite
Apartment in Newry
4.95 out of 5 average rating, 111 reviews

Sunday River Resort Condos @Cascades

KarenRating, 5 stars1 month ago
A good ski in ski out location. Perfect for us. Thank you.

Quick stats about holiday rentals that are kid-friendly in Chebeague Island

  • Total rentals

    20 properties

  • Nightly prices starting at

    £67 before taxes and fees

  • Total number of reviews

    520 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore