
Family-friendly vacation rentals in Maryland Beach
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Top-rated family-friendly rentals in Maryland Beach
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB
After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!
4.93 out of 5 average rating, 290 reviews
Beautiful waterview 2B condo w/Dock&Close to Beach
Welcome to the Canal Bungalow! A stylish 1000 sq. foot retreat to enjoy all the fun & relaxation of the coastal lifestyle in North Oc. Bring your boat with you and dock alongside your back porch, enjoy pool access in a private gated community, or bring your sports gear for Northside Park. We are tucked away on the quiet bayside of OC & only a few minutes walk to the beach. Unwind on our beautiful balcony while watching the boats go by & finally understand the true meaning of a coastal lifestyle!
5.0 out of 5 average rating, 123 reviews
3 BR Waterfront Home, Minutes to the Beach
Recently updated waterfront house located in the family-friendly Montego Bay community. Enjoy beautiful sunsets on the back deck or hop in one of the kayaks for a paddle around the wide-open canal. Try your hand at crabbing or fishing off the dock to catch your dinner. Within easy walking distance of the beach and Northside Park (about 10 minutes walk to both). Beach chairs, toys, boogie boards, and umbrellas are yours to use for fun in the sand and surf. The dock is available for boat tie-ups.
4.93 out of 5 average rating, 152 reviews
Direct Oceanfront Newly Renovated W/ Pool 2 Bd
A slice of paradise on the 18th floor! This fully renovated beachfront condo boasts breathtaking views of the glistening ocean. With two bedrooms and two modern baths, this haven offers the perfect blend of luxury and comfort. Imagine waking up to the sound of waves crashing and sipping your morning coffee overlooking the endless horizon. Whether you're lounging by the shimmering pool or strolling along the pristine shoreline, every moment here is infused with the tranquility of coastal living.
4.99 out of 5 average rating, 107 reviews
Walk to the Beach! PingPong-Fenced Yard-N64-Bikes!
Escape to the Blue House, a pet-friendly retreat just 6-mins to the beach. - Full kitchen and charcoal grill - Coffee bar (k-cups, espresso, coffee grinder, french press, and pour over) - Fully fenced patio with a fire pit and ping pong - Outdoor shower - 5 Bikes - Northside Park - 2 min walk away - N64 - 48W EV charger - Record player - Pet ramp Sleep 10 (8 Adults 2 Children) in our 3 bedrooms - 1 king, 1 queen, 1 full over full bunk bed, and full sofa bed. NOT POSTED ON C.LIST
4.99 out of 5 average rating, 101 reviews
Oceanfront Condo w/ Resort Amenities 3BDR &3pools
Sea Watch Condo's is an ideal family location with tons of amenities. The until is a recently updated 3 bedroom 2 bathroom condo that sleeps 6 people in 2 queen beds, 2 twin beds . The unit is ocean front with a large oceanfront balcony. The amenities Include, basketball court, tennis courts, playground, arcade, movie theater, billiard room, indoor pool and outdoor pool as well as a restaurant. The condo has 24 hour security and plenty of parking. Pools closed in off season
4.88 out of 5 average rating, 146 reviews
Direct Oceanfront with a View and Amenities Galore
Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.
4.94 out of 5 average rating, 339 reviews
Beach Side Condo on Quiet Bunting Ave.
Welcome to our Fenwick Island beach condo! Less than a one minute walk until your toes are sinking into beautiful Delaware beach sand. Beautifully decorated 3 bedroom 2 full bath condo, beach-view balcony and carport. Perfectly situated in quiet Fenwick Island on coveted Bunting Ave. Boardwalks, go-carts, mini-golf within 5 min walk. We cherish our lovely little home away from home, and we hope that you do too. Bed sheets are included, however, towels & toiletries are not.
4.93 out of 5 average rating, 187 reviews
Steps to the Beach, Ocean View 1BR, Renovated
Steps to the beach! Fully renovated, bright, modern, clean condo with a balcony view of the ocean. Quiet North Ocean City location with walking distance to restaurants, bus, 7-11, Mini golf course, movie theater, parks, etc. Brand new appliances and furniture. Free WiFi, King Size Bed, 60" & 40" TVs. Pull Out Queen Sofa, Brand New Full Bathroom. Washer and Dryer in the unit. Keurig Coffee Station, iPhone Charging station. Private balcony. Free Parking Space.
4.99 out of 5 average rating, 358 reviews
Stunning Bayview Home with Own Private Pool
This home can be occupied by a max of 12 adults with a total of 15 including children. Come relax in this gorgeous bay view single-family home in the lovely Caine's Woods neighborhood of Ocean City, adjacent to Fenwick Island. Imagine lazy days spent on the beach followed by a dip in the pool outside the kitchen door! GUESTS USE POOL AT THEIR OWN RISK! The pool is open from May 1- September 30. Obviously we can’t have it open during cold temperatures!
4.98 out of 5 average rating, 162 reviews
Water Front Condo w/Pool Short Walk to Beach
FIRST FLOOR UNIT Bayside Condominium Sleeps 4 - 6 max Walking Distance to Northside Park Walk to the Ocean , don't worry about beach parking NON SMOKING 1 Bedroom 1 Bath condo, First floor unit with an outside deck This Air Conditioned, One Bedroom Condo has a fully equipped kitchen, washer/dryer, full refrigerator. There is a Queen bed and a full bed along with 1 Queen Sleep sofa in the living room *MUST BE 21 OR OVER* No Pets!
4.89 out of 5 average rating, 187 reviews
21st Floor Carousel - 2 BR Oceanfront & Bay View
NEW!! Welcome to our direct oceanfront 2 bedroom & 2 bath unit at the Carousel! Bringing the comfort of your home to the beach! Bring the whole family for lots of fun memories! We strive to take care of this condo to ensure you have a relaxing, comfortable, and clean stay! Our condo includes 2 DOUBLE SIZED balconies! An oceanfront balcony and a bay view balcony! You can enjoy both the sunrise and sunset!
4.96 out of 5 average rating, 119 reviewsPopular amenities for Maryland Beach family-friendly rentals
Family-friendly home rentals with a hot tub

Luxury Oceanfront Oasis!
4.95 out of 5 average rating, 108 reviews
Luxe Oceanfront 1BR | Pool, Hot Tub, Sun Deck
4.82 out of 5 average rating, 130 reviews
Oceanfront Paradise | Pool | Hot Tub | Beach
4.92 out of 5 average rating, 292 reviews
Stunning! Fun, family friendly! Walk to beach!
4.99 out of 5 average rating, 124 reviews
Oceanfront Carousel building, Swimming Pools!
4.9 out of 5 average rating, 133 reviews
Spacious Bayside 2 BR Condo at Sunset Bay
4.95 out of 5 average rating, 118 reviews
Sleep in a One-of-a-Kind Barn near Ocean City Mary
4.98 out of 5 average rating, 320 reviews
Featured on HGTV! Bethany Beach Ocean Front Condo
4.89 out of 5 average rating, 138 reviewsFamily- and pet-friendly home rentals

Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.
4.97 out of 5 average rating, 162 reviews
Pet Friendly SFH w/ fenced yard, 2blocks to BEACH!
4.95 out of 5 average rating, 212 reviews
Dolores by the Sea- Family Groups ONLY
4.97 out of 5 average rating, 109 reviews
Hall Cottage, Fenwick Island, DE
4.86 out of 5 average rating, 212 reviews
Stunning private waterfront suite
4.95 out of 5 average rating, 423 reviews
The Laurel House - Large fenced in yard!
4.97 out of 5 average rating, 185 reviews
One Bedroom Beachfront Apartment Mid-Town
4.9 out of 5 average rating, 137 reviews
McKinley Duplex
4.91 out of 5 average rating, 139 reviewsFamily-friendly home rentals with a pool

Gone Coastal | Bay Views, Pool | Top Floor
4.97 out of 5 average rating, 124 reviews
1st Floor Canal Front POOL 2 Blocks 2 Beach/Park
4.97 out of 5 average rating, 116 reviews
2 BdrmOceanfront-Pool, Xbox, Pickleball, Gym, WiFi
4.88 out of 5 average rating, 185 reviews
Ocean Front Condo
4.97 out of 5 average rating, 102 reviews
Nice 2 BR Oceanfront, Year Round Fun & Amenities!
4.91 out of 5 average rating, 330 reviews
Sunshine By The Sea near Bethany Beach
4.98 out of 5 average rating, 153 reviews
Oceanfront Balcony • Pool • North Ocean City
5.0 out of 5 average rating, 25 reviews
North OC 3BR + Loft Sleeps 12 Walk to Pool & Beach
5.0 out of 5 average rating, 18 reviewsDestinations to explore
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- Family-friendly rentals United States
- Chincoteague Island
- Cape May Beach NJ
- Assateague Island National Seashore
- Wildwood Crest Beach New Jersey
- Ocean City Beach
- Broadkill Beach
- Rehoboth Beach
- Bethany Beach Boardwalk
- Assateague State Park
- Cape Henlopen State Park
- Willow Creek Winery & Farm
- Northside Park
- Wildwood Boardwalk
- Delaware Seashore State Park
- Jolly Roger Amusement Park
- Fenwick Island State Park Beach
- Stone Harbor Beach
- Roland E Powell Convention Center
- Wildwoods Convention Center
- Ocean Pines Golf Club
- Mariner's Arcade
- Ocean City Boardwalk
- Funland
- Bear Trap Dunes





