Pet-friendly holiday rentals in Maryland Beach

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!

Perfect location!

This charming 2-bedroom condo is perfectly located in Ocean City to take full advantage of the beach lifestyle. Imagine relaxing on your covered outdoor balcony, enjoying warm and breezy weather while taking in the sights--including being able to see the bay. You'll be a quick walk to the Boardwalk and all major downtown locations. The interior is beautifully-maintained with loads of character, including laminate flooring and custom wainscotin. Available for all Ocean City events....25+ require

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!

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.

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.

IslandCoveParadise:LuxNewlyBuilt-Brdwk pool/2CarGg

We welcome you, your family and friends to stay at our luxury, Newly Built, beautifully furnished, & decorated 3 BR 3.5 BA w/2 parking garage spaces plus free street parking, and an outdoor pool on 25th street. Relax and enjoy the AMAZING VIEW on the water front from our triple balconies, just 2 blocks (3-4 minutes walk) from the boardwalk & the beach. Steps from Jolly Rogers Amusement Park and many miniature golf courses. Within walking distance are restaurants/, shopping, & nightlife.

Studio Charm w/ Deck: Walk to Beach & Dining!

This charming OC studio promises nothing but good vibes! The studio has a full bath, an open layout with an electric fireplace, a fully equipped kitchen, and washer and dryer. Relax on the private balcony, sipping a drink in a hanging chair or dining at the patio table. Proximity to Jolly Roger Amusement Park and Splash Mountain Water Park adds to the excitement, while numerous restaurants and shops are a short stroll away. The beach and boardwalk are just a few blocks from your doorstep!

Ocean-front getaway, amazing views, 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.

Sea Dunes King Suite, Exclusive Private Beach - DOG FRIENDLY!

Unwind and chill in this boho coastal inspired guest suite on the ocean side. At Sea Dunes' private guest king suite, the surf and sand are steps away. Get ready to pack your cooler and enjoy a day in the sun on this beautiful, private dog-friendly beach. Sea Dunes is located in Fenwick Island, DE and nestled between protected state nature parks. Just a short trip in the car to a marina with watersports, kayak adventures on the bay, local dining, farm markets and shopping.

Hobbs & Rose | A Peaceful Cottage Escape

Built in 1941 from historic “clinker bricks,” this restored cottage is a dreamy place to slow down and reconnect. Surrounded by enchanted gardens and close to the beach, Hobbs & Rose is filled with charm—gorgeous living spaces, a carved marble soaking tub, and thoughtful details throughout. Enjoy a romantic getaway and unwind in our Sanctuary meditation room, where birdsong and forest friends welcome you. You relax—we’ve created every detail to help you feel restored.

Cozy Condo Oasis with Adorable Private Patio

Adorably cozy two-bedroom dog friendly condo just blocks away from the beach. First floor corner unit adds to its charm! Enjoy this first-floor oasis in the Caine Woods neighborhood of Ocean City. Only two blocks from beaches, bayside restaurants, breakfast nooks, and Delaware! Soak up some shade on the private patio after a long day at the beach or walk on over to Harpoon Hannas for dinner and live music with a view. This unit is two steps up the front porch.

The Laurel House - Large fenced in yard!

Recently renovated 3 bedroom, 2 bath with outside shower. 1625 square foot single family home with fenced-in yard in the Caine Woods section of North Ocean City. 2 Smart TV's, 2 TV'S with Roku, all with Netflix, Comcast, and fast Wi-Fi. Complete kitchen including dishwasher. Two off street parking spaces with ample free street parking in area. Short 5 block walk to the beach. Nearby shops, restaurants, community area, and amusements all in walking distance.