
Family-friendly holiday rentals in Maryland Beach
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Top-rated family-friendly rentals in Maryland Beach
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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!
KitchenIndoor spacesBackyard
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!
Indoor spacesFamilyCondition
5.0 out of 5 average rating, 122 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.
KitchenFamilyCleanliness
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.
Indoor spacesFamilyOutdoor spaces
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
KitchenFamilyAccess
4.99 out of 5 average rating, 101 reviews
Oceanfront 1 Bedroom, Balcony, Sitting Room, Pool
Opal Osprey: This OVERSIZE one-bedroom condo has been completely remodeled... giant oceanfront balcony PLUS a large patio room on the bayside! Expansive ocean views from every angle, super easy beach access, wonderful atmosphere in the quiet north end of OC. Linens included! Property Amenities - King size bed & queen sleeper - Large outdoor pool - Elevators - Dedicated high-speed WiFi and router w/ ethernet (Xfinity 100Mbps) - 2 Smart TVS with Xfinity, Roku - Keyless check-in 24/7
FamilyIndoor spacesSleep quality
4.95 out of 5 average rating, 190 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
KitchenFamilyNearby
4.88 out of 5 average rating, 145 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.
FamilyIndoor spacesDecor
4.94 out of 5 average rating, 338 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.
FamilyIndoor spacesComfort
4.92 out of 5 average rating, 186 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.
KitchenFamilyView
4.99 out of 5 average rating, 357 reviews
Hall Cottage, Fenwick Island, Delaware
Charming, updated cottage. Wifi and space to work. Located between Bethany Beach, DE and Ocean City, MD, Fenwick is known as 'The Quiet Resort.' Two blocks to the beach. The cottage is the perfect size for a couple or small family. Sitting on a lovely, quiet block, between the ocean and the bay, the cottage is a quick walk to fine dining, pubs and shopping. The cottage comes with two beach chairs and an umbrella, an outdoor shower, and a beach parking pass.
KitchenIndoor spacesAccuracy
4.86 out of 5 average rating, 212 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!
Indoor spacesFamilyDecor
4.96 out of 5 average rating, 118 reviewsPopular amenities for Maryland Beach family-friendly rentals
Family-friendly home rentals with a hot tub

Luxury Oceanfront Oasis!
Indoor spacesKitchenAccuracy
4.95 out of 5 average rating, 107 reviews
Designer Oceanfront Condo | Pool, Hot Tub & Deck
KitchenFamilyHot tub
4.97 out of 5 average rating, 104 reviews
Stunning! Fun, family friendly! Walk to beach!
FamilyIndoor spacesEV charging
4.99 out of 5 average rating, 124 reviews
Oceanfront Paradise | Pool | Hot Tub | Beach
KitchenIndoor spacesPool
4.92 out of 5 average rating, 291 reviews
Sleep in a One-of-a-Kind Barn near Ocean City Mary
Indoor spacesFamilyBarbecue
4.98 out of 5 average rating, 318 reviews
Uncle Buck's Cottage
KitchenIndoor spacesParking
4.91 out of 5 average rating, 107 reviews
Spacious Bayside 2 BR Condo at Sunset Bay
FamilyIndoor spacesWalkability
4.95 out of 5 average rating, 118 reviews
Oceanfront Carousel building, Swimming Pools!
Indoor spacesKitchenCleanliness
4.9 out of 5 average rating, 133 reviewsFamily- and pet-friendly home rentals

Stunning Bayview Home with Own Private Pool
FamilyIndoor spacesAmenities
4.98 out of 5 average rating, 162 reviews
Pet Friendly SFH w/ fenced yard, 2blocks to BEACH!
FamilyIndoor spacesAccess
4.95 out of 5 average rating, 211 reviews
Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.
KitchenFamilyLocation
4.97 out of 5 average rating, 162 reviews
Dolores by the Sea- Family Groups ONLY
KitchenIndoor spacesAccess
4.97 out of 5 average rating, 109 reviews
One Bedroom Beachfront Apartment Mid-Town
KitchenIndoor spacesCheck-in
4.9 out of 5 average rating, 135 reviews
Stunning private waterfront suite
KitchenIndoor spacesPool
4.95 out of 5 average rating, 423 reviews
Delightful Skoolie Near Bethany Beach
Indoor spacesFamilyPets
4.95 out of 5 average rating, 191 reviews
Sea Dunes King Suite, Exclusive Private Beach - DOG FRIENDLY!
Indoor spacesKitchenQuiet
4.83 out of 5 average rating, 136 reviewsFamily-friendly home rentals with a pool

1st Floor Canal Front POOL 2 Blocks 2 Beach/Park
Indoor spacesFamilyBathroom
4.97 out of 5 average rating, 115 reviews
Nice 2 BR Oceanfront, Year Round Fun & Amenities!
KitchenIndoor spacesGetting around
4.91 out of 5 average rating, 328 reviews
Oceanfront Balcony • Pool • North Ocean City
Indoor spacesFamilySleep quality
5.0 out of 5 average rating, 24 reviews
North OC 3BR + Loft Sleeps 12 Walk to Pool & Beach
KitchenFamilyLayout
5.0 out of 5 average rating, 18 reviews
Lighthouse Bay Luxury Townhome | Arcade Loft
KitchenFamilyValue
5.0 out of 5 average rating, 14 reviews
Oceanfront•Pool • Private Balcony w/Sunrise Views
FamilyIndoor spacesBathroom
4.92 out of 5 average rating, 37 reviews
2 BR 2BA North Ocean City Condo
Indoor spacesKitchenHospitality
4.93 out of 5 average rating, 58 reviews
Beachside Luxe: Pool, Ensuite & Family Favorite
Indoor spacesKitchenAccuracy
5.0 out of 5 average rating, 33 reviewsDestinations to explore
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- 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
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- Fenwick Island State Park Beach
- Stone Harbor Beach
- Roland E Powell Convention Center
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- Ocean Pines Golf Club
- Mariner's Arcade
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- Funland
- Bear Trap Dunes





