Family-friendly holiday rentals in Assateague Island

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Assateague Island family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Dewey Beach
4.96 out of 5 average rating, 170 reviews

McAvoy B & B

DimitrisRating, 5 stars3 days ago
Highly recommended! The house is at a great location, is clean and spacious, and the host is very responsive and friendly. Would go back again!
Guest favourite
Apartment in Bethany Beach
4.87 out of 5 average rating, 138 reviews

Sea Colony Beach And Tennis Resort

TjRating, 5 stars2 days ago
Condo was clean airy open beachy and felt like home. Location is close enough to beach to walk. You can walk into town as well. Or there are free shuttles and trams that come with the sea colony badge. All in all it’s a great stay great location and most importantly -relaxing!
Guest favourite
Villa in Ocean View
4.89 out of 5 average rating, 151 reviews

3 BR 1st floor condo, near beach, resort community

KelliRating, 5 stars1 month ago
We appreciated your quick responses and helpful recommendations. Staying with Beth was a pleasure. The location was perfect, the home was cozy and Beth was always available to answer our questions. Highly recommended!”
Superhost
Condo in Bethany Beach
4.89 out of 5 average rating, 176 reviews

Beautiful Beach-View Condo

EricaRating, 5 stars3 weeks ago
We loved Raj’s place! We have two young children and his place was fully equipped to entertain them with books, toys, etc. Best Airbnb we have stayed in so far 😊
Guest favourite
Condo in Rehoboth Beach
4.94 out of 5 average rating, 164 reviews

Classy Beach Getaway

VickiRating, 5 stars1 week ago
We loved staying at Adair’s place. Her home was as pictured and very comfortable for our group of 3. It is beautifully decorated and the location is peaceful and convenient to the bike trail, restaurants and an easy walk to downtown Rehoboth. We had one item in need of repair and Adair responded right away. We highly recommend her place and hope to stay there again.
Superhost
Condo in Bethany Beach
4.88 out of 5 average rating, 121 reviews

Featured on HGTV! Bethany Beach Ocean Front Condo

NinaRating, 5 stars2 weeks ago
Better view than the pic shows! The private beach was clean and very close to the condo. Rentable chairs and umbrellas available on the beach. There are 2 chairs and umbrellas in the condo to use. Some of the furnishings could use a freshen-up. Mattress was excellent and we are picky! The place was very clean upon arrival and the owner was very responsive to any questions we had! Bethany Beach Boardwalk is less than a mile and a delightful treat with great restaurants and shops along with beach access- something we did not expect and thoroughly enjoyed!
Guest favourite
Home in Rehoboth Beach
4.87 out of 5 average rating, 231 reviews

Dodd House Beach Home w/private pool and hot tub

KerryRating, 5 stars2 days ago
Our family enjoyed the Dodd home. There was adequate space for everyone. We loved the location which was in close proximity to Dewey and Rehoboth beach. The kids really enjoyed having a pool. They said they don’t want to go to a hotel ever again. We enjoyed cooking on the grill & playing games in the evening. We can’t forget to mention the wonderful hot tub. It was such a great added attraction. We will return next year for sure.
Superhost
Townhouse in Bethany Beach
4.92 out of 5 average rating, 110 reviews

Lakefront slps 6; beach, pools, tennis, gym, view!

ValeriaRating, 5 stars11 months ago
Sherri’s place is awesome and the community and surroundings are beautiful. The kitchen is furnished with everything you need for cooking. The deck is such a plus, with the view of the pond and the ducks, as well as the private little beach. The community is very friendly and walkable, and the different options for pools were very fun for us to explore. Taking walks in the morning was amazing. It is very close to Bethany “downtown” and 6 min drive to the beach. You can also walk or take the tram. I had a great time with my kids and would definitely recommend and come back!

Family- and pet-friendly home rentals

Guest favourite
Home in Bethany Beach
4.94 out of 5 average rating, 115 reviews

Bethany Beach 116 5th St Oceanblock

LynnRating, 5 stars1 week ago
We loved our stay! The house was beautiful with lots of space and exceptionally well stocked. The pictures really don’t do it justice. We spent a lot of time on the very comfortable screened in porch. A few nice surprises: the water pressure was fantastic, the washer and dryer are huge, and there was ample fridge space upstairs and a second one on the first floor. Paul was also very responsive during our stay and very nice! We’d love to come back again!
Superhost
Cottage in Chincoteague
4.72 out of 5 average rating, 100 reviews

SNUG HARBOR waterfront cottage with a grand view!

AlexandraRating, 5 stars2 weeks ago
We ABSOLUTELY loved our visit, and plan to return and stay with Basia! Our weekend consisted of rainy weather and she offered us a covered porch which was well worth it!! Each morning we had a peaceful water view with the horses in the distance. I don’t think it could get any better. The boat tour was SO much fun. Basia stayed in contact with us about when would be the better time to go. She really looked out for us when the weather would be at its peak. Her recommendations never failed to impress. Thank you SO much for having us!! We plan to be back.
Top Guest favourite
Townhouse in Dewey Beach
4.9 out of 5 average rating, 122 reviews

McKinley Duplex

JessRating, 5 stars1 month ago
We loved our stay in Dewey Beach, the home was a great location near the beach and great shops and restaurants. The kitchen was stocked with everything we could need and more to make our stay feel right at home. We'll definitely stay here again when in Dewey!
Guest favourite
Condo in Dewey Beach
4.88 out of 5 average rating, 196 reviews

Read Ave Dewey Condo - Bay Front, Private Beach

AngelinaRating, 5 stars3 weeks ago
Very nice and easy check in and check out.
Guest favourite
Condo in Dewey Beach
4.85 out of 5 average rating, 198 reviews

On the Bay, Private Beach-Boat Slip

JohnRating, 5 stars1 month ago
Catherine's place was great for our family and young son. The location is tremendous and there are great views just eating breakfast and sipping morning coffee. The place itself is well stocked and has a very efficient layout (pocket doors) for the space. Catherine was super responsive and understanding, we really enjoyed our stay.
Top Guest favourite
Home in Salisbury
4.87 out of 5 average rating, 124 reviews

Hudson House

KarenRating, 5 stars1 week ago
This house is very spacious, comfortable and very homey. We had a great stay! We were initially concerned about it having only one and half bathrooms but once we were there we didn’t even notice it. The bathroom is so big and the half bathroom is ideally situated at the other end of the house, which was very convenient. We would definitely recommend it and will book it again on our next trip to Salisbury.
Top Guest favourite
Home in Rehoboth Beach
4.9 out of 5 average rating, 120 reviews

Luxury Carriage House in Rehoboth Beach

LoriRating, 5 stars3 weeks ago
Linda was so friendly and responsive to all my questions. Her place is absolutely beautiful, clean, close to the beach and shopping outlets. It felt like home away from home. She thought about every need for her guests, even having bike available! This was my first time booking an Airbnb and the experience will absolutely make me a returning customer.
Guest favourite
Townhouse in Rehoboth Beach
4.97 out of 5 average rating, 179 reviews

Walk to Beach, 3B/3B Dewey Beach Summer Rental

PhillipRating, 5 stars1 month ago
Christie was incredibly helpful and nice! I booked her home super last min and I was able to get right in. Big plus was having many channels on the tv for the evenings (those who book beach spots know many places have some random package) she had network TV (great for my niece!) A gem of a location as well! Would 100% return.

Family-friendly home rentals with a pool

Superhost
Condo in Ocean City
4.79 out of 5 average rating, 108 reviews

Spacious Direct Oceanfront 1BR Condo w/Balconies

ChrisRating, 5 stars3 weeks ago
Location was excellent right on the beach with a beautiful view of the ocean. The property was easy to find and the security guard at the front desk was super helpful getting us squared away with anything we needed. The condo had great amenities including a nice big fridge and stove, not to mention it has cable television for when you are relaxing (most Airbnb's do not offer this). 5/5 stars for everything except the bed (I am used to a firm bed and this one was beyond soft). We would absolutely stay here again though and I highly suggest this place for a nice getaway. Thanks, Natallia, for being a great host!
Superhost
Condo in Rehoboth Beach
4.89 out of 5 average rating, 147 reviews

Right on Silver Lake walk to the beach and town!

WilliamRating, 5 stars6 days ago
I can't say enough good things about Ana and this lovely condo. First things first, Ana as a host is everything you'd wish for- friendly, sincere, gracious, patient and very helpful! A week and a half before check-in, my sister had a specific question about parking in town so I asked Ana. She took the time to point me in the right direction and also suggested Salt Air for the kind of restaurant we wanted. And she was right! This condo is lovely, I've been going to turtle bridge for years so the proximity to the bridge and Silver Lake was wonderful. We are already daydreaming of when we'll come back. Nothing is more soothing than sitting with your morning tea and checking emails with the lake moving so close to you. We were able to go out and play badminton, walk to the market, walk into town and visit our old friends- just a dream. I even had to leave half a day early, unexpectedly- everything was smooth. I forgot to throw away my mouthwash bottle in the bathroom when leaving- sorry!
Guest favourite
Townhouse in Frankford
4.86 out of 5 average rating, 120 reviews

Seaside Getaway: Bethany Beach Charm

JacquelineRating, 5 stars2 days ago
Our family had a wonderful time exploring and enjoying the area. It was nice to have a clean, comfortable space to come back to. It have everything we needed to cook, we enjoyed the games, and we especially enjoyed the back porch room. I read and had my coffee in there every morning. We really enjoyed our stay and were very happy with our accommodations.
Top Guest favourite
Condo in Ocean City
4.96 out of 5 average rating, 153 reviews

Waterview, Steps from Beach, Linens Included!

NaydaRating, 5 starstoday
⭐️⭐️⭐️⭐️⭐️ A Perfect Beach Getaway for Families This condo was absolutely beautiful and spacious—perfect for our group of 8 (two families). The location couldn’t be better: right on the beach and within walking distance to many shops, restaurants, and attractions. We loved waking up early to catch the sunrise with our little ones, such a peaceful and unforgettable part of our trip! The condo had everything we needed to feel right at home, and we were all very comfortable throughout our stay. We would definitely come back and highly recommend this place to other families looking for a relaxing and convenient stay in Ocean City!
Superhost
Apartment in Ocean City
4.9 out of 5 average rating, 141 reviews

Bayside Beach Getaway

JohnRating, 5 stars1 week ago
I come to Ocean City every June with a couple of my employees for an annual conference and we always get an AirBnb, Bayside Beach Getaway was perfect! The location was excellent for us and close to everything, much of it within walking distance; restaurants, convenience stores etc as Coastal Hwy was just 50 ft away. The host communicated with me quickly and clearly and the check-in was flawless. When we arrived, we found a very nice, very clean condo with plenty of room. Our schedule was such that we ate breakfasts and lunches at the condo before and after the conference. The kitchen was well stocked with everything we needed to cook our meals. We enjoyed sitting out on the deck in the evenings which overlooked the water. I would highly recommend this condo!
Superhost
Townhouse in Ocean City
4.85 out of 5 average rating, 196 reviews

DownByTheBay 115- Waterfront/4BR/Sleep 15/Pool

RobinRating, 5 stars1 month ago
We all loved this place, my family wanted to stay longer. It is so lovely and relaxing. Great location. Thanks for everything!
Top Guest favourite
Home in Rehoboth Beach
5 out of 5 average rating, 195 reviews

Beautiful Beach House in Rehoboth

RebeccaRating, 5 stars2 weeks ago
Had the absolute best time staying at this gem. The house is stunning and Autumn was a fantastic host! The house is spacious and open. It was exactly as described but better. We couldn’t have been happier. Will definitely be back!
Guest favourite
Condo in Rehoboth Beach
4.82 out of 5 average rating, 381 reviews

2 Bedroom Condo Rehoboth Beach w/ No Chores

LeianaRating, 5 stars1 week ago
Beautiful place! Walked everyday to the beach and it was not too difficult. Very nice and comfy place.

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