Pet-friendly holiday rentals in Ocean Pines

Guest suite in Ocean Pines

A cozy living area features a white couch and two accent chairs with a leaf pattern. A glass coffee table sits on a woven area rug. Large sliding doors provide a view of the outdoor patio, framed by greenery and water, enhancing the space's natural light.

4.95 out of 5 average rating, 390 reviews

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!

4.95 out of 5 average rating, 168 reviews

A two-story beach cottage is shown, featuring a spacious upper deck with outdoor seating and vibrant green chairs situated on a sandy area below. A stairway provides access to the deck, while the clean white siding complements the clear blue sky.

Cottage in Ocean City

Pet Friendly - West OC Cottage Fenced yard!

Pet Family - near Sunset Marina Hangout & chill in cozy beach cottage YEAR ROUND, close to serene Assateaque Island, many walkable restaurants. This is Pet friendly with fenced yard-bring your 4 legged friends! Sit by the backyard fire pit while looking at the magnificent star filled sky & hear the fishing boats come & go! Fun place! ORDER YOUR CRABS TO GO & sit on enclosed porch to eat & enjoy! Take a break with the beautiful setting! Relax and enjoy with your furry family-Peaceful but FUN!

4.94 out of 5 average rating, 136 reviews

A living room features light blue seating arranged around a coffee table, complemented by a decorative cabinet and a large television. Natural light filters through the window, enhancing the tranquility of the space, which is accented by a ceiling fan and wall art above the entrance.

Home in Selbyville

Central Haven with Great Fenced Yard

You will be close to everything when you stay in this centrally-located home. The rear deck and grill are great for enjoying time outside. There's a fenced rear yard, making this home a perfect choice for man's best friend. We welcome dogs of any breed, size, and weight. We do offer size-specific pet amenities, so please share a photo of your dog when booking, or provide a basic description so we can set out appropriate amenities. For those traveling with cats, please inquire before booking.

A two-story blue house is framed by trees, with a well-maintained front yard. The home features black shutters and white steps leading to a central door. A porch flag and a welcoming bench are visible, enhancing the inviting exterior.

4.96 out of 5 average rating, 138 reviews

Little house in Berlin, Md.

Our home is located in Ocean Pines, Maryland. Spend the day at the beach, golf, come back and relax on our spacious screened porch. The community has 5 pools, walking trails, Parks, and more. The house is a short drive to Ocean City, Md. (8 Miles) via Rt. 90 or Rt. 50. Assateague Island National Seashore is also just a short drive 12 miles. You can see wild horses, beautiful sunsets, ride bikes, or go to the beach. There are many golf courses within 15 miles of the house all very nice.

4.86 out of 5 average rating, 112 reviews

A modern kitchen is showcased with a dark refrigerator and sleek stainless steel appliances. A central island features a light granite countertop, while decorative shelves display dishware against a vibrant blue wall. Pendant lights illuminate the area, enhancing the functional layout.

Home in Ocean View

Pet Friendly | New EV Charger - New 100’ Fence!

NEW Fence JUST INSTALLED! 7 Hudson is a COMPLETELY renovated, three-bedroom, two full bathroom / family & pet friendly cottage that has everything you need for the perfect getaway. With 55” TV’s in every room. Located less than one mile to the town of Bethany Beach and within walking distance to restaurants, walking trails, parks, and other attractions. There are no CO producing appliances. Hardwired CO monitors on both floors. Thank you for your interest. (King bedroom on 1st & 2nd floor)

4.99 out of 5 average rating, 190 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 Coastal Cottage with Modern Amenities

Built from “clinker bricks” in 1941 to house poultry feed, this Airbnb is a dreamy place to slow down. Exposed wood beams and interior brick walls as well as all the luxuries required for a rural escape. 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!

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, 220 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.

A spacious living room features a comfortable dark sofa, two brown chairs, and a cozy fireplace. Natural light enters through large windows adorned with light blue drapes. A ceiling fan and recessed lighting contribute to a bright and airy atmosphere, complemented by modern decor.

4.99 out of 5 average rating, 101 reviews

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!

4.9 out of 5 average rating, 132 reviews

A cozy living area features a comfortable beige sofa, a wooden dining table set for four, and a television mounted on the wall. Natural light enters from a nearby door leading to an outdoor space. A ceiling fan enhances the airy atmosphere, complemented by cheerful decor.

Apartment in Ocean City

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....

Guest suite in Fenwick Island

A cozy guest suite is presented, featuring a spacious bed covered with a vibrant blue blanket. Decorative elements include a light-colored rug and a plant next to the bed. A small bookshelf and artwork adorn the walls, contributing to the room's inviting decor.

4.81 out of 5 average rating, 113 reviews

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.

A modern kitchen features light grey cabinetry and stainless steel appliances. A round table is set for dining, accompanied by stylish metal chairs. Natural light filters through the window, enhancing the warm, inviting layout that connects seamlessly to adjacent living spaces.

4.84 out of 5 average rating, 135 reviews

Peaceful Beach Cottage - Sanitized & WiFi!

Fully renovated clean, sanitized, quaint house in a quiet neighborhood minutes from the beach/ocean! Community offers many amenities such as pools, restaurants, playgrounds, etc. Have peace and quiet while only being minutes from the beach and main OC drag. Very close to the casino! Voted "#1 Safest Neighborhood in Maryland!" *June-August we only accept 7 day rentals with a Saturday check in* *Memorial & Labor Day weekends have 3 night minimum with Fri check in*

A charming bungalow features dark blue siding and large front windows, framed by neatly trimmed bushes. A concrete walkway leads to the front door, and a well-maintained lawn surrounds the home. The sky is partly cloudy, adding to the inviting exterior.

4.95 out of 5 average rating, 183 reviews

Pet Friendly SFH w/ fenced yard, 2blocks to BEACH!

PET FRIENDLY with fenced in yard, 2 blocks to the beach! 2024 Summer rentals avail. Sunday - Sunday. An 8min walk to the beaches of N. Ocean City! Our home is located in a quiet neighborhood, between the beach & bay! You'll have access to a fenced backyard, full kitchen, smart TV, & WIFI. We expect guests to be courteous to neighbors. Parties & loud music are not permitted. **Not traveling with pets? Check out our ocean side condo near Northside Park!**

Popular amenities for Ocean Pines pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.94 out of 5 average rating, 118 reviews

A two-story beach house features a spacious front porch with white railings, providing ample seating. The elevated structure is supported by two pillars, with parking available underneath. Lush greenery is visible in the front yard, adding to the welcoming ambiance.

Home in Bethany Beach

Bethany Beach 116 5th St Oceanblock

4.91 out of 5 average rating, 118 reviews

A screened porch features a cozy seating arrangement with white wicker chairs adorned with colorful cushions and a small table. A lantern adds a decorative touch, while an artistic crab painting is visible on the wall. The space overlooks a green area through the screen.

Home in Frankford

Tranquil Times-Pet Friendly 5 mi to Bethany Beach

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.

4.84 out of 5 average rating, 101 reviews

Ocean City Townhome by Beach Bayside

A modern kitchen showcases a spacious island with seating for four. Elegant cabinetry and stainless-steel appliances complete the design. Natural light floods the area, highlighting the marble countertop and the decorative accessories. A large TV is mounted on the wall for convenience.

5 out of 5 average rating, 50 reviews

New waterfront home on bay, quick walk to beach

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.

4.97 out of 5 average rating, 169 reviews

The Laurel House - Large fenced in yard!

A single-story home with a well-kept exterior is surrounded by trees, providing a serene setting. A covered porch with railings welcomes guests, while a gravel driveway leads to the entrance. The property features a reliable trash can and is nestled within a natural landscape.

4.98 out of 5 average rating, 43 reviews

Tranquil Waters, OceanPines, 3 br, Dog Friendly

A modern dining area features a rectangular table surrounded by six upholstered chairs. Large windows allow natural light to fill the space, with views of the surrounding trees. A stylish light fixture hangs above the table, and a door leads to the outdoor deck.

5 out of 5 average rating, 66 reviews

OC Gateway: Modern 4BR/2.5BA home (dog friendly)

A spacious living area features a wood-paneled ceiling and large windows, providing a sweeping view of the St. Martin River. Comfortable seating arrangements include dark sofas and a wooden dining table, complemented by natural light flowing into the room.

5 out of 5 average rating, 18 reviews

Villa Caribbean OCMD

Pet-friendly home rentals with a pool

4.9 out of 5 average rating, 30 reviews

A light-filled room features a cozy gray sofa and a large bean bag chair with decorative pillows. Three framed ocean-themed prints decorate the walls, contributing to a calming ambiance. Natural light streams through two white-framed windows with light blinds, illuminating the space.

Flat in Ocean City

Mermaid Cove

4.93 out of 5 average rating, 14 reviews

Peace in the Pines- 3BD, 2BA w/ Beach Club Pass

4.92 out of 5 average rating, 180 reviews

The exterior of the multi-story townhouse is presented along a serene waterway. Balconies are visible on the front, while a clear blue sky reflects onto the calm waters. Boat docks are positioned nearby, enhancing the waterfront atmosphere.

Townhouse in Ocean City

IslandCoveParadise:LuxNewlyBuilt-Brdwk pool/2CarGg

5 out of 5 average rating, 93 reviews

The living area is spacious, featuring a light blue wall color and a large sectional sofa. Natural light floods through windows, illuminating the decorative rug. The outdoor porch includes dining furniture and offers views of the canal and neighboring buildings.

Apartment in Ocean City

Beautiful waterview 2B condo w/Dock&Close to Beach

4.93 out of 5 average rating, 84 reviews

An aerial view of a marina with multiple boats docked along a well-maintained pathway. The surrounding residential community and parking area are visible, as sunlight reflects off the peaceful water, highlighting the scenic environment.

Townhouse in Ocean Pines

OceanPinesFamilyBeachRetreat~JettdTub~KingBed~Golf

Holiday home in Ocean City

A golden sunset is seen over the calm ocean waves, casting a warm reflection on the water's surface. The view is framed by a railing, providing a serene backdrop that highlights the beauty of the evening sky.

4.71 out of 5 average rating, 51 reviews

Spacious Ocean View Condo

4.81 out of 5 average rating, 54 reviews

A colorful welcome sign features a vintage-style van in teal and white, adorned with a yellow surfboard. The word 'welcome' is artistically integrated with a flower design, creating an inviting entryway statement.

Home in Sussex County

Endless Summer at Bethany Beach

5 out of 5 average rating, 9 reviews

An elegant entrance is showcased with a wide staircase leading to a grand front door framed by tall windows. Flanking the entrance, stacked stone pillars support the roof, and a patterned stone walkway is bordered by landscaped areas, enhancing the welcoming ambiance.

Home in Dagsboro

Pristine 4+ acre waterfront in Bethany Beach area

Private, pet-friendly home rentals

4.94 out of 5 average rating, 51 reviews

The exterior of a charming blue cottage is surrounded by lush greenery and vibrant pink flowers. A spacious front porch is visible, complete with white railings. The entrance features an arched window above the door, creating an inviting entrance that blends with the natural surroundings.

Cottage in Ocean Pines

Rhapsody in Blue Beach Cottage Ocean Pines, OC MD

A tranquil waterfront scene captures a canal-side home surrounded by lush greenery. A private boat slip is visible alongside the property, accommodating boats up to 23' long. The sun-filled exterior features a light-colored facade and a cozy patio, enhancing the serene atmosphere.

5 out of 5 average rating, 21 reviews

Waterfront Vacation Home in Ocean Pines

4.95 out of 5 average rating, 38 reviews

A sunset view captures the vibrant colors of the sky reflecting over the bay. The silhouette of a building is visible in the distance, surrounded by lush greenery and marshland. Calm waters mirror the hues of orange, pink, and blue, creating a serene landscape.

Townhouse in Ocean City

Ocean City Bayside Getaway

5 out of 5 average rating, 84 reviews

A well-maintained house features a light-colored exterior surrounded by landscaped flower beds. A gravel driveway leads to the entrance, which is adorned with potted plants. Lush greenery and a distant building are visible in the background beneath a partly cloudy sky.

Home in Selbyville

Lighthouse Cottage- Pet Friendly & Close to beach

4.8 out of 5 average rating, 15 reviews

A light-filled living area showcases a navy sofa facing a mounted television. A striped ottoman sits on a woven rug, while a plant adds a touch of greenery. Dining chairs and natural light from surrounding windows create an inviting space for relaxation.

Cottage in Ocean City

Bungalow 611

4.95 out of 5 average rating, 43 reviews

A cozy living room is presented with two striped sofas facing a wooden coffee table. A wicker chair and a lamp are included, complemented by a large area rug. Natural light streams through multiple windows covered with white blinds.

Home in Ocean View

Pet Friendly Comfort Bethany Beach

The exterior of a cozy cottage is framed by lush landscaping, including colorful flowers and greenery. A flagpole displays an American flag, and a path leads to a screened-in porch, providing an inviting entrance to the home.

5 out of 5 average rating, 36 reviews

Cozy & cute two bedroom beach cottage.

A living area showcases a comfortable layout with two dark sofas, accent pillows, and a wooden coffee table. A large area rug features a blend of soft blue hues. The space is warmly lit, with a dining area visible in the background and cabinetry seen in the kitchen.