Family-friendly holiday rentals in Maryland Beach

4.9 out of 5 average rating, 608 reviews

A charming tiny house features wooden shingles and a welcoming front door. It is framed by colorful flowers in a garden, enhancing the outdoor landscape. A sign above the door adds a personal touch, while large windows allow natural light to fill the space.

Home in Ocean View

Tiny House at Good Earth, near Bethany Beach

A custom 165 sq. ft. "Tiny House" located right between our theater and the 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 TV and internet in the unit. We have 2 on-site restuarants, market, theater, and parking. Our AIRBNB village consists of 2 tiny houses, 2 cottages, tent sites, a loft appartment, and more! Staying at Good Earth is more than a beach trip!

4.99 out of 5 average rating, 266 reviews

A welcoming space is featured, showcasing a luxurious jacuzzi with a wooden tray holding candles and decor. Nearby, a cozy living area with a modern couch is highlighted against an artistic forest mural. An adorable Highland cow stands nearby, adding a touch of rustic charm.

Ranch in Selbyville

Ranch Stay- Farm Animals, Jacuzzi, Arcade, Beaches

Welcome to the Swedish Cowboy, your ultimate escape! This unique BARNDOMINIUM home is designed to offer a memorable retreat for up to four (4) guests, with the flexibility to accommodate two (2) additional guests for a small fee. Enjoy the charming backyard where you can meet a variety of fuzzy and feathered friends or head inside and play on the arcade or relax in the jacuzzi. Perfectly situated near popular beaches and bustling boardwalks, you'll have plenty of options for fun and relaxation.

An open-concept living and dining area features a wooden dining table set for six, complemented by modern chairs. A comfortable seating arrangement with light-colored couches is situated near large windows, offering views of the surrounding area. A mounted TV and decorative elements enhance the space.

4.96 out of 5 average rating, 122 reviews

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom

Launch your fabulous beach getaway at amenity-rich Sunset Cove at Sea Watch, part of an oceanfront condo complex offering 3 pools, complimentary movie theater, game room, gym, and much more. Enjoy spectacular ocean and bay views from 2 balconies, smart TVs in every bedroom and living room with provided satellite programming, fully equipped kitchen, comfortable living and bedroom spaces–and that’s just the beginning as your group has a blast at the beach and all of Ocean City’s fun attractions.

4.97 out of 5 average rating, 197 reviews

A serene waterfront scene is captured at sunset, with vibrant colors reflected in the calm water. A charming building with large windows is illuminated, surrounded by lush trees, and boats are docked along the waterfront, creating a peaceful atmosphere.

Apartment in Ocean Pines

Pines Getaway - Berlin Tree Light & Ice Ice 11/28

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

4.99 out of 5 average rating, 196 reviews

A charming cottage facade is framed by white columns and features a gabled roof. Two black rocking chairs, adorned with pillows, sit on a brick porch surrounded by colorful potted flowers. Lush greenery enhances the inviting atmosphere.

Cottage in Frankford

19th Century Cottage with Modern Amenities

Book your Hallmark Christmas stay today, fully decorated by Thanksgiving until the end of January!! Built from “clinker bricks” in 1941 to house poultry feed, this Airbnb is a dreamy place to slow down. This charming cottage near the beach & is surrounded by enchanted gardens. You will swoon over the carved marble bathtub and gorgeous living areas. Perfect for a romantic getaway, Hobbs and Rose Cottage is waiting to create a memorable experience for you! NEW for 2025, our mediation room!

4.96 out of 5 average rating, 483 reviews

The living area features large sliding doors that open to a porch with stunning bay views during sunset. A neutral-colored couch and a cozy chair create a welcoming space. A wooden dining table complements the serene atmosphere, illuminated by the warm glow from the setting sun.

Townhouse in Ocean City

Edgewater Escape - Luxury Bayfront Loft with Porch

You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown 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 roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

4.83 out of 5 average rating, 277 reviews

A charming beach cottage is displayed in an A-frame design, featuring a large front porch with white railings. Windows are covered by striped awnings, allowing natural light to filter in. The landscaped yard includes low shrubbery, adding to the inviting exterior.

Cottage in Bethany Beach

A-mazing Beach Cottage on Canal & Trolley Route

Welcome to our beach house! An "A"dorable cottage located on Bethany Canal, an easy walk, bike ride, or trolley to the Boardwalk and BEACH! Perfect for families (comfortably sleeps 4 adults and plus children), and small groups of friends alike! 3 bedrooms, 1 full bathroom, plus an enclosed outdoor shower. Very clean, tons of natural light, and plenty of outdoor space -- including a relaxing and bright sunroom/porch, small deck out back with a grill, and large front porch.

The living area features soft blue furnishings and a light wood coffee table. Floor-to-ceiling windows offer direct views of the ocean, while two lamps provide warm lighting. A coastal-themed artwork adorns the wall, enhancing the serene atmosphere of the space.

4.95 out of 5 average rating, 300 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.

A cozy living area displays a light blue color scheme. A white sofa is positioned beside a coffee table on a patterned rug, while a dining table is set nearby. Floor-to-ceiling sliding doors open to a balcony, offering views of the ocean.

4.96 out of 5 average rating, 282 reviews

Caramar Couples Retreat

This cute little first floor efficiency condo is ocean front for a perfect vacation to the beach. It’s an older building but has been partially renovated and updated. You can get to the beach by a very short walk through a private walkway from the condo building. The view from the private balcony is perfect and relaxing. WiFi provided upon check in- xfinity, Netflix, and internet. Indoor and outdoor dining areas and a full kitchen. Closet and dresser for storage use.

An open-concept living area is featured with beach-inspired decor, a spacious sofa, and a dining table for six. Large sliding glass doors provide access to an oceanfront balcony with stunning views. A ceiling fan is installed for added comfort.

4.99 out of 5 average rating, 145 reviews

🌊Carousel Oceanfront 2 Bedroom Amazing Amenities

Welcome to our 2 bedroom 2 bath ocean front unit at the Carousel. We take care of this condo ourselves to ensure you have a comfortable, clean and well stocked place to stay. This unit sleeps 6, one king bed, one queen bed and one queen sofa bed. There is an ocean front balcony & a bay view balcony. Washer & Dryer, ice skating, indoor pool, outdoor pool, game room, restaurant & bar, snack shop, gym & sauna & more!!! Please read all details below.

A serene ocean view is presented from a private balcony, featuring two teal chairs. The sandy beach stretches into the distance, with gentle waves lapping at the shore. A clear sky completes the tranquil coastal scene, creating a peaceful atmosphere.

4.92 out of 5 average rating, 255 reviews

Sun, Sand & Sea | Your Cozy Oceanfront Hideaway

-Oceanfront -Indoor pool & Hot tub -Walk to local dining and shopping -Elevator accessible plus luggage carts -Full kitchen for cooking meals -Fast Wifi and Streaming TVs -Fully Stocked Home: Clean linens, towels, toilet paper, paper towels & more! **2025 guests: Our pool and hot tub are in the process of being renovated and will be closed during your stay. This does not impact our condo, but you will not be able to use these amenities.**

An open-concept living space features comfortable seating, including a cozy sofa and accent chair. A dining area with modern chairs complements an equipped kitchen, showcasing stylish cabinetry and stainless-steel appliances. Large windows offer expansive views of the ocean and bright natural light.