Family-friendly vacation rentals in Assateague Island

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Assateague Island

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in Ocean City

4.91 out of 5 average rating, 290 reviews

Ocean Front 802 Midtown Oasis Pool & Parking

CONSTRUCTION NOTICE NOV 24 to MAY 25 balcony may be inaccessible, noise may be heard Wake up to the ocean sunrise in this modern 2 bedroom, completely renovated, condo. Prime location on 29th street, 2 blocks north of the famous OC Boardwalk, 2 blocks east of OC's premier amusement and water park along with two famous crab house and other restaurants within walking distance. One hassle free off street parking spot, free WIFI, full size washer & dryer, and a beautiful outdoor pool steps from t

Guest favorite

Guest suite in Ocean Pines

4.95 out of 5 average rating, 373 reviews

Stunning private waterfront suite

Welcome to your cozy getaway with stunning water views from every room! This sweet 2-bedroom, 1-bath suite boasts a private entrance, a living room, and a cute kitchenette. Nestled in a peaceful, family-friendly neighborhood, you'll have year-round access to swimming pools, a golf course, tennis courts, a Yacht club, and lovely parks nearby. Only a quick 10-minute drive lands you on the sandy beaches and lively Boardwalk of Ocean City. Park in the driveway and step into your own private escape!

Guest favorite

Condo in Ocean City

4.96 out of 5 average rating, 142 reviews

Mid-Town OC! Ocean Block... Steps to the Beach!

OCEAN VIEW and STEPS to the BEACH... Newly remodeled in 2023! 2 bed/2 bath condo with ocean & bay views is located in desirable mid-town Ocean City. Walk to dining, shopping, convention center, amusements & nightlife. Be in the middle of everything, but still have a quiet place to relax. **Summer Months - check-ins on Mon & Fri ONLY Memorial Day to Labor Day. Book Weeks or Mini-weeks. (Weeks: Fri - Fri OR Mon - Mon) (Mini-Weeks: Mon to Fri OR Fri to Mon). *Other months check-in any night

Guest favorite

Home in Berlin

4.79 out of 5 average rating, 193 reviews

OC, Md great amenities in community, near beaches

MERMAID DREAMS where you can just have FUN or just RELAX. We are 5 miles out from OC and Assateague beaches. Our community, Assateague Pointe, is a beautiful gated community, with 2 great pools, baby pool, big splash pool, a rec center, a fishing/crabbing pier, pond with paddle boats, 2 playgrounds+ more. For kiddos of all ages, we are located right next door to Frontier Town, which has awesome water slides , western shows, mini golf, a rope course, ice cream shop.. short term stays ONLY

Guest favorite

Cottage in Onancock

4.95 out of 5 average rating, 152 reviews

A "True" Chesapeake Bay Waterfront Experience!

Get away from it all... The Thicket Point Fish Camp is a true Chesapeake Bay waterfront property and the perfect place to escape for the best of the Eastern Shore. Located just 5 miles from downtown Onancock, VA, and everyday conveniences, this property is one of a kind! This is the "Sunset House" expanded and completely renovated in May 2018, It is complemented by our "Bayside House" - also available on Airbnb. Be ready for the smell of the salt air and to enjoy million-dollar sunsets!

Guest favorite

Townhouse in Ocean City

4.97 out of 5 average rating, 397 reviews

Edgewater Escape - Bayfront Condo w/Private Porch

Welcome to our "Edgewater Escape." These buildings were built in the 1960's and literally hang entirely over the bay in downtown in Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a king sized bed and the downstairs couch pulls out into a comfortable queen bed. Full size kitchen with microwave, fridge, electric range, and coffee maker. Located on 7th street, over the bay :)

Guest favorite

Home in Ocean View

4.9 out of 5 average rating, 564 reviews

Tiny House at Good Earth, near Bethany Beach

A custom-built "Tiny House" located right between our new dinner theater and our garden dining area. True to the show "Tiny House Nation"; cool interior with custom woodwork, stairs to a lofted bed. Fully functioning kitchen. Spacious bathroom & shower. We provide TVs and internet in the units but the quality of service is not guaranteed. We are in a rural area and sometimes it's slow or not working at all. If TV and internet are super important for your stay we may not be the right fit.

Guest favorite

Tiny home in Accomac

4.93 out of 5 average rating, 471 reviews

Little Red House on a Farm - Quiet Rural Waterview

The Little Red House VA is a tiny house with big charm. This rural cottage on a 50 acre farm is nestled between peaceful fields, woods, marsh and creek. Curated with hygge comfort and efficiency in mind, you'll love the natural light and serene decor. • Epic stargazing • Heavenly private outdoor shower • Firepit with wood provided • Ample open spaces • Peace and quiet for sleeping • Comfy patio seating for chilling, coffee, and cocktails • Fast WIFI. • Proud Superhost for 10+ years!

Guest favorite

Home in Chincoteague Island

4.91 out of 5 average rating, 198 reviews

We’ve Thought of Everything So You Can Relax!

Relax and enjoy nature in our home with a light and airy coastal feel in every room. Get away from the sights and sounds of traffic and city chaos in our private, secluded cul-de-sac location. Take a peek at the water through the trees from our private, second floor deck. Listen to the song birds, ducks, toads and frogs all flourishing in the undeveloped lots surrounding our property.

Guest favorite

Condo in Ocean City

4.98 out of 5 average rating, 209 reviews

Direct Oceanfront close to Northside Park!

Location, location, location! 2 bed, 2 bath direct oceanfront condo, with incredible ocean sunrise views from your private enclosed patio. Master bedroom features unbelievable views of the ocean, glass slider out to the patio & in suite full bath! Walking distance to Northside Park, restaurants & shopping. 2 assigned parking spaces. Elevator or steps - you pick. Washer/dryer in unit.

Guest favorite

Home in Ocean View

4.88 out of 5 average rating, 493 reviews

Private place near Bethany Beach

Our place is close to Bethany Beach and conveniently located to Fenwick Island, Ocean City Maryland, Rehoboth Beach, Tax Free Outlet Shopping, Golf, Fishing, Surfing, or Hunting. You’ll love our place because of the quiet wooded location perfect for relaxing near all the beaches of the Delaware Eastern shore. This area is a wonderful place to visit all year round.

Guest favorite

Home in Chincoteague

4.95 out of 5 average rating, 111 reviews

Chincoteague Island Blue Pearl

Welcome to the Blue Pearl. Built in the roaring 20’s this quaint 2 bedroom 2 bath home will take you back to a simpler time . Our island home has been renovated to provide an open and airy feeling while keeping its old world charm. Located one block from downtown shops and restaurants are just a short stroll. No pets!