House holiday rentals in Maryland Beach

A light and airy deck features a rectangular dining table surrounded by aqua-colored chairs. A calm water view is visible beyond the railing, with flags gently waving in the breeze. Soft lighting is provided by string lights overhead, enhancing the inviting atmosphere.

4.94 out of 5 average rating, 278 reviews

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!

4.9 out of 5 average rating, 610 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!

A back deck features a seating area composed of a sofa and ottoman with soft cushions, facing a calm canal. A wooden table is positioned nearby. A red umbrella is closed and stands beside the seating, while a sunset casts gentle hues across the water.

4.93 out of 5 average rating, 127 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.

4.98 out of 5 average rating, 137 reviews

The exterior of a single-story house is visible, featuring a spacious front porch with white railings. Large windows allow natural light to enter, while a driveway provides parking for two vehicles. A wooded area surrounds the property, enhancing its peaceful setting.

Home in Ocean Pines

Camelot

HIGHEST RATED HOUSE IN OCEAN PINES! CHECK OUT OUR AMAZING GUEST REVIEWS :) Jumpstart your ultimate beach getaway at this impressive 3-bedroom, 2-bathroom retreat house! Complete with amenity-packed living spaces with vaulted ceilings and a serene location, you’ll never hunger for entertainment at this family friendly home. Grill out on the patio, roast marshmallows by the fire pit, tee off at a nearby golf course, or enjoy some retail therapy at Outlets Ocean City! A short drive to the beach!

5 out of 5 average rating, 5 reviews

The exterior of a single-story home is presented, featuring a light gray facade with dark shutters. A two-car garage is visible on the left, while a welcoming front porch offers seating. Well-maintained landscaping with green shrubs frames the entrance, completing the inviting curb appeal.

Home in Clarksville

Gorgeous Home at Ocean View Beach Club

Your vacation awaits. This gorgeous 3-bedroom, 2 -bath, single-story home in the sort after resort of Ocean View Beach Club awaits. Relax with your family and friends in this home built for entertainment in a community with so many amenities, you will struggle to decide what to do. Nestled just minutes from Bethany Beach and area restaurants, Ocean View Beach Club has it all. Large outdoor pool, fitness center, vibrant clubhouse, library, shuttle service to downtown Bethany, need I say more?

Superhost

The living room features large windows adorned with floral-patterned drapes, allowing natural light to fill the space. Two comfortable chairs, including a recliner and a plush seating option, are positioned next to a coffee table. A television rests on a light-colored media unit, enhancing the room's functionality.

4.82 out of 5 average rating, 110 reviews

Ocean City Townhome by Beach Bayside

If you're looking for a vacation home, consider this convenient duplex located just a few blocks from the beach. Situated on the second floor, this vacation rental offers all the necessary amenities for a comfortable stay with Food lion, Target and Marshalls nearby. Enjoy a short, seven-minute walk to Harpoon Hanna's, a local restaurant hotspot. For entertainment, Jolly Roger Amusement Park, James Farm Ecological Preserve, Roland Convention Center, host regular sports events and live shows.

A spacious living area is furnished with two dark leather sofas, providing ample seating. A ceiling fan enhances airflow. The open layout connects to a dining area featuring wooden chairs, while the kitchen is visible in the background, showcasing modern appliances and cabinetry.

4.94 out of 5 average rating, 231 reviews

Right behind Alley Oops & Crab Bag. Walk to beach

Look no further! With Alley OOps in the backyard and a 5-minute walk to the beach, pool, tennis, and shopping, the fun is endless. This 3 bedroom, 2 bathroom house has high-end furniture, fast wifi, 4 flat screens and 2 free parking spots with street parking when available. Our Community offers all of these amenities included in your rental and free putt-putt too! Enjoy our natural wood-burning fireplace and large porch to take in the sunset through the trees. We do not rent to under 25.

Superhost

4.77 out of 5 average rating, 13 reviews

2BR Bungalow -patio space-dog friendly- sleeps 4

Escape to this remodeled yet classic Key West-inspired bungalow on 142nd St. in bayside Ocean City, MD! Blending modern updates with Old Ocean City vintage charm, this pet-friendly 2-bedroom, 1-bath retreat offers 1,000 sq. ft. of cozy coastal living. Enjoy beautiful outdoor seating surrounded by lush tropical foliage, private parking, perfect for families and friends. Just minutes from the beach, dining, and attractions, this unique getaway is ideal for relaxation and adventure.

4.96 out of 5 average rating, 28 reviews

Family Fun! 3-Bed Home next to Playground & Park

Relax and recharge in this bright, peaceful home in the highly desirable Caine Woods neighborhood of north Ocean City! Park-front living with new pickleball and tennis courts plus a playground right outside your door—perfect for families! Just three short blocks to the beach! Walk to mini-golf, arcades, and great dining. Enjoy two comfortable living areas, three spacious bedrooms, a fully equipped kitchen, three full baths, and two furnished decks with grill and dining space.

Two large windows frame the expansive ocean view, providing natural light to the living space. The scene features sandy beach dunes leading towards the water, where the calm blue ocean meets the clear sky.

4.9 out of 5 average rating, 141 reviews

Closest condo to the beach in OC! Dog Friendly!

Perfect getaway to the ocean in this updated, stylish home. Elevated ocean-front, with stunning views from every room and two private balconies. Amazing location - walk to great restaurants and still enjoy a private-feeling beach with lifeguard stand just steps away. No need to 'pack' for the beach -the house is just steps away. Enjoy coffee at the granite island overlooking the beach! There is a set of stairs up to the condo, and another set of stairs up to the main bedroom.

A spacious living area is highlighted by large windows offering sweeping ocean views. Comfortably arranged seating includes a striped sofa and a cozy armchair. A light-colored coffee table sits on a textured rug, while a bar area connects to the kitchen, enhancing the open layout.

4.88 out of 5 average rating, 8 reviews

Oceanfront 2 Bed/2Bath,IndoorPool,Game Room

Wake up to ocean sunrises and unwind with bay sunsets from your private balcony at Water Temple! This bright 2BR/2BA condo in the Capri building sleeps 6 and offers stunning water views from nearly every room. Enjoy a full kitchen, in-unit laundry, free WiFi, and access to an indoor pool, sun deck, fitness center, game room, and library. Walk to the beach, dining, and attractions — perfect for families and friends seeking an unforgettable Ocean City getaway!

A charming two-story home is framed by lush greenery and features a welcoming front porch with white railings. Skylights adorn the roof, allowing natural light to flood the interior. A spacious driveway provides access to the home while a mailbox stands at the curb.