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!

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!

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.

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!

Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.

Relax with the family in this comfortable and charming home. There is room for 8 to sleep comfortably. The dining room and breakfast nook offer plenty of seating for all with a spacious kitchen. Our corner lot offers the option for outdoor fun like slip and slide, corn hole, frisbee, and more! Nearby: Beach, Bay, Wildlife sanctuary surrounded by a walking trail, Pool, Tennis, restaurants & Eventful Northside Park! Quiet and peaceful location to make family or romantic memories of a lifetime.

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines

Beautifully updated and recently renovated, rancher on a great street in Ocean Pines perfect for families and adults looking for a relaxing stay. We offer 3 bedrooms and 2 bathrooms on one level, with new large flat screen TV's, stainless appliances, and everything you'll need for your stay. We have a large driveway and a screened patio. Ocean Pines boasts over a dozen parks and walking trails, a public Yacht Club, 5 pools, 2 marinas, and a championship golf course - 10 min to the beach!

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.

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.

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.