Family-friendly holiday rentals in Drakes Island Beach

Perfect stay for 4 adults, 1 infant, and 1 dog! Love the two-bedroom, two-bathroom layout, plus the kitchenette to make oatmeal and toast in the morning before hitting the ski trails. Clear check-in instructions, no hassle at all even when we arrived around midnight.

10/10 would recommend - Mary Alice’s place is comfortable & cozy. Very well equipped for a getaway to beautiful Kittery! She’s also a wonderful and helpful host.

Meghan's home was a perfect place to stay for my sister's Bachelorette weekend! The home is located in a quiet community with views of the river and bay, and it was conveniently located with just a short drive into the heart of Portland. We found our stay extremely comfortable, especially on such a cold and dreary April weekend. Meghan had the hottub ready for us with matching robes for all which was a fun surprise. Check in and check out were a breeze. We even took a breakfast recommendation from the guest book (Forage Market, yum!), a tasty experience indeed. Thanks again, Meghan!

We had the most amazing stay at Madawaska! Amazing views from the bedroom and hot tub in a beautiful, peaceful, and private location overlooking the water. And such a wonderful design of the cabin. We will definitely be back!

Large, bright, spacious beach house just steps from the beach and a short walk from the more bustling areas of OOB. Ocean views from all floors. Spacious enough for groups to be together but also to have some privacy if need be. Comfortable beds and well stocked kitchen. Lovely patio with spacious hot tub, outdoor dining area and small yard. A great spot with a responsive host!

Great place. The bed was really comfortable. Hot tub was nice and private and relaxing.

We just had a wonderful ladie's weekend at Christy's place! We lucked out and got a bit of snow, so the cabin was the perfect cozy spot to spend the weekend with a fire and a puzzle! The hot tub was an extra added bonus! Beds were all very comfortable and living room was super cozy. Very easy ride to downtown for restaurants and shopping for a bit. Would definitely recommend!

Gorgeous grounds and location for a quiet peaceful weekend getaway! David was very responsive and personable. The cabin is eclectic with something new and interesting in every corner.

Me and my party enjoyed every minute of our stay at Tom’s cabin! The cabin itself was spacious, cozy, and clean. The surroundings were also beautiful, right next to a nice neighborhood and lake. Thomas was a fantastic host and was extremely friendly and helpful. He was always there to answer questions and help out when needed. Overall, amazing trip and I would 100% go back!

This is the kind of airbnb I'm excited to visit and support -- really lovely, cozy place with a lot of character and everything we needed to make ourselves at home for a week. The proximity to Chocorua is fantastic and it's a good spring board to the lakes region & and the White Mountains. Becky is fantastic - super friendly, responsive, and kind. The wifi was strong enough for me to work there for a few days and we had all the supplies we needed to cook for ourselves. The only issue was the road noise, which was pretty loud during the day, but thankfully quieter in the nights.

My wife and I just returned from this property. This was our fourth consecutive annual visit and we have already reserved for 2025. When it comes down to it, there are only 2 things that are important and draw us back time after time. 1. The home and its views: We have had the opportunity to stay at a number of New England Airbnb/VRBO properties, this is the only one we want to return to, over and over again. Its popularity makes it difficult to reserve- please ask yourself why? The home is delightful, comfortable, affordable, well equipped, clean, private and with a view of Sargent's pond that never stops mesmerizing us. If you are an outdoor action or more of laid-back type - no one will be disappointed. 2. Andy and Emily are the quintessential hosts. From the welcoming package, including doggie snacks - they think of everything. They are kind, honest and thoughtful people who want to ensure your needs are met but are never intrusive. We sincerely trust and thank them.

let me start out by saying this house is exactly as described and depicted on the website. plenty of room for 6 adults and 2 bigger kids. enough seating space, kitchen utensils, linens, towels. the game room was a big hit for the old and young boys. the moms lived the warm, cozy sunroof. the house has great windows with lots of light. it was spotlessly clean. a snowplow took care of the storm..plowing and shoveling several times..Judith was easy to work with. instructions , as well as things to do, were available in a binder. we had a great week and all hope to come back here.

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.

Absolutely love this place! The life of the brewery and the community is simply unmatched :) the hosts were warm, friendly and super responsive

As one kiddo said at the end “this is the best weekend ever!” This was the perfect getaway and wished we had more time! Stayed 4 adults and three kids with a dog and had more than enough space! The layout of the house was perfect, as having bedrooms on each side of the house! An incredible area so close to town. 30 minutes to North Conway and just minutes to good food! King Pine is also 20 minutes which has multiple winter activities. The house is also so close to the lake! The space was cozy, had everything you needed, comfortable beds, and what a great surprise to have a dryer for the wet clothes after a day in the snow! Matt was a great host, helpful, fast, and responsive. Would stay here again!

We loved our stay at Katie's house in Portland. It was very comfortable, clean and nicely decorated. We would love to stay again soon!

Our stay at the beach house was great! You couldn't be closer to the water! So much fun kayaking, floating and swimming in the lake! House is much better than the pictures do it justice. For a 2 bedroom house its very big and spacious, beds were extremely comfortable. The no wifi was a little bit of a downer but there were plenty of board games to play. There is some street noise but not bad at all. Would most definitely recommend if you are looking for waterfront property. The access to the resort pool was a plus too for the kiddos!

Clean and good storage for a small space. Good location

Had a wonderful stay at Christophers place. He is a great host, always responsive with clear instructions. Place was peaceful, private and is exactly same as it was in the pictures. Will come soon!

Great place to stay in Ogunquit area! The cottage is exactly as described, and well located between Wells and Ogunquit - you do need a car to get around easily as others have said. This is a fantastic place to stay with kids - having the pool facilities especially is great as a break from the beach. Julie and Derek left great advice as well as flexibility on check-in - thanks again!

Rita was responsive, friendly, and accommodating. Place was clean and inviting, close to the strip. Would definitely stay again!

Donna is fantastic and if your looking for a charming New England spot this is it! We Are very satisfied with this home.

We absolutely loved our visit to Appledore Cottage! It was quaint and perfectly relaxing. The screened in porch was the best place to just sit…very quiet and peaceful!

Home is very expansive with room for multiple families to reside together. Lots of games and activities for all ages. Amazing location within minutes to airport and short drive to downtown