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Kid-friendly holiday rentals in Cumberland

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Cumberland family-friendly rentals

Kid-friendly house rentals

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.
Guest favourite
Home in Wells
5 out of 5 average rating, 26 reviews

Updated 2 Bedroom Private House near beaches

AnnemarieRating, 5 stars6 months ago
We had a great stay in Tara's home. It is located in a quiet neighborhood and is close to our favorite towns- Ogunquit and Kennebunkport. We had plenty of room for the four of us. We loved the outside spaces and the open floor plan. Tara was very easy to communicate with and very responsive. The instructions for check in and check out were very clear. We hope to return in the future!
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!
Guest favourite
Home in Kennebunkport
4.86 out of 5 average rating, 175 reviews

Kennebunkport House - Walk to Dock Square!

MaryRating, 5 stars3 weeks ago
We had a fantastic stay! The house was in a perfect location; peaceful, private, and still just a short walk to dinner spots, which made everything so easy. There was plenty of space for lounging and gathering, and more than enough bathrooms for everyone (a huge plus!). The house had everything we needed for a relaxing weekend away. Cozy, quiet, and super comfortable; we’ll definitely be back! Highly recommend.
Guest favourite
Home in Old Orchard Beach
4.83 out of 5 average rating, 60 reviews

Feb/April school breaks available. 8 bedrooms

RoniRating, 5 stars3 months ago
This was our 4th year staying at Sandy Cove to celebrate Christmas with our entire family. There are plenty of bedrooms and bathrooms to accommodate overnight stays. We love the 2 dining room tables and refrigerators. We had a small issue with a clog in the kitchen sink. I reached out to Mike and he sent someone over to fix it within a few hours. We hope to stay again next year!
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.
Superhost
Home in Kennebunk
4.66 out of 5 average rating, 59 reviews

The Timeless Retreat | Walk to Downtown Kennebunk

TraceyRating, 5 stars2 months ago
Loved this home. Plenty of space for a girls getaway weekend away from the hustle & bustle! Everything has been re-done in this home and was a really fun weekend. Very comfortable and host was very responsive. Rob shoved the driveway prior to our arrival & We knew there was snow expected so brought some rock salt and shovels to keep the walk area safe!

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!
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!
Superhost
Flat in West End
4.78 out of 5 average rating, 729 reviews

BEST location! HUGE 1 bedroom downtown Portland

PhilippeRating, 5 stars1 month ago
Very well located apartment, with large living room and bed room, small kitchen and tiny bathroom. Communication with Sharon was easy and responsive.

Family-friendly apartment rentals

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 !!
Superhost
Apartment in Downtown Portland
4.84 out of 5 average rating, 298 reviews

Old Port on foot

LenRating, 5 stars5 days ago
Thus was a great location for our stay in Portland. Easy to get around and plenty to see and do nearby. i will definitely stay here again when I'm in the area.
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
C’est l’endroit parfait ! Tout est très propre, et il ne manque rien! Kevin est très sympathique. Il a été de bons conseils. J’ai toujours rêvé de venir à OOB l’hiver et j’ai vraiment aimé l’expérience! Nous avons adoré notre séjour. Avec son emplacement et ses portes patios doubles, la vue est splendide! Pour les amateurs du bruit des vagues, de la vue de la mer, des levés de soleil, des longues marches à la plage… c’est l’endroit idéal!
Guest favourite
Apartment in Wells
4.84 out of 5 average rating, 178 reviews

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

BernadetteRating, 5 stars1 month ago
Très beau logement, propre et disposant de tout! La communication avec Christopher avant et pendant notre séjour était excellente !
Guest favourite
Apartment in Scarborough
4.96 out of 5 average rating, 346 reviews

Cozy condo by the beach!

QuinnRating, 5 stars2 weeks ago
I had an amazing stay. Place was just as described and was the perfect location for a weekend getaway!
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!!!!
Guest favourite
Apartment in South Portland
4.95 out of 5 average rating, 168 reviews

Rustic Willard Beach condo ten mins from Old Port!

NaimaRating, 5 stars1 week ago
What a wonderful place in a lovely neighborhood. The condo exceeded our expectations—it was even more beautiful in person. We had a comfortable, happy stay with our small children. Scratch Bakery and an ice cream parlor are right across the street! And the book collection was great. Highly recommend!

Quick stats about holiday rentals that are kid-friendly in Cumberland

  • Total rentals

    60 properties

  • Nightly prices starting at

    £37 before taxes and fees

  • Total number of reviews

    3.8K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore