Pet-friendly holiday rentals in Ocean Pines

5.0 out of 5 average rating, 123 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.

Condo in Ocean City

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!

WalkabilityOutdoor spacesView

The front exterior of a charming two-story house is shown, featuring a pitched roof and light-colored siding. A bright blue door welcomes visitors. A white picket fence encloses the front yard, which is neatly landscaped with greenery and flowering plants.

4.97 out of 5 average rating, 109 reviews

Dolores by the Sea- Family Groups ONLY

This recently remodeled 1950's house is walking distance to the beach, boardwalk, & fabulous restaurants. Tucked away from the hustle & bustle in a quiet neighborhood this cozy home is the perfect place to relax after a fun filled day at the beach. This home has 4 bedrooms & up to 7 beds. With a wheelchair ramp & a fenced in yard this house is perfect for family gatherings & making memories. Please note that due to neighborhood restrictions we cannot book to unrelated renters under 27 years old

Outdoor spacesWalkabilityAccuracy

Guest suite in Ocean Pines

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!

Outdoor spacesWalkabilityEV charging

4.95 out of 5 average rating, 423 reviews

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.

4.95 out of 5 average rating, 150 reviews

Little house in Berlin, Md.

Our home is located in Ocean Pines, Maryland. The house is a short drive to Ocean City, Md. (8 Miles). Spend the day at the beach, golfing, fishing come back and relax on our spacious screened porch. The community has 5 pools, walking trails, Parks, and more. Assateague Island National Seashore is also just a short drive 12 miles. You can see wild horses, beautiful sunsets, ride bikes, drive on the beach. There are many golf courses within 15 miles of the house and a casino 2 miles away.

Outdoor spacesPetsAccess

A cozy living area features a light gray sofa adorned with decorative pillows and a small blue ottoman. Natural light brightens the space, showcasing art on the walls and a dining area in the background, complemented by a wooden table and chairs.

4.87 out of 5 average rating, 108 reviews

Home Away from Home , Pet friendly retreat

Welcome to Ocean Pines Getaway, Enter home through a beautiful covered porch with swing for two and lovely seating area. This sweet home has 3 bedrooms & 2 full baths. A fully stocked kitchen , with eat in breakfast nook, Also proper dining room plenty of seating for family Cozy living room with working fireplace. All season sunroom plenty of seating, pub table & bar. Doggie door in sunroom large enough for 100 lb dog, leads to fenced in backyard. $100 pet fee and $125 linens & bath towels.

WalkabilityOutdoor spacesDecor

A spacious living area features two sofas, one in dark leather and the other in a light fabric, arranged around a low wooden coffee table. A flat-screen TV is mounted on a light wall above a stone fireplace, adding a cozy touch to the room.

4.97 out of 5 average rating, 162 reviews

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.

WalkabilityOutdoor spacesFamily

4.94 out of 5 average rating, 174 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.

WalkabilityOutdoor spacesQuiet

4.99 out of 5 average rating, 101 reviews

Villa in Ocean City

Walk to the Beach! PingPong-Fenced Yard-N64-Bikes!

Escape to the Blue House, a pet-friendly retreat just 6-mins to the beach. - Full kitchen and charcoal grill - Coffee bar (k-cups, espresso, coffee grinder, french press, and pour over) - Fully fenced patio with a fire pit and ping pong - Outdoor shower - 5 Bikes - Northside Park - 2 min walk away - N64 - 48W EV charger - Record player - Pet ramp Sleep 10 (8 Adults 2 Children) in our 3 bedrooms - 1 king, 1 queen, 1 full over full bunk bed, and full sofa bed. NOT POSTED ON C.LIST

PetsWalkabilityKitchen

A waterfront backyard features sandy areas lined with a white picket fence. A picnic table is positioned on the beach, facing the calm waterway. Houses are visible along the banks, framed by trees and distant structures under a soft evening sky.

4.92 out of 5 average rating, 213 reviews

Waterfront Beach Home in the Ocean City, MD Area

There is room for 8 adults (plus 2 kids). Located in the premiere seaside community in the Ocean City area, Ocean Pines, this wonderful waterfront home provides amazing views both day and night. The open floor plan provides guests with lots of room to socialize and bond, but also has secluded bedrooms that provides needed privacy. The outdoor living area is to die for. Sit back and watch the sun set over the canal while you catch up with friends or loved one. Use our bikes!

PetsOutdoor spacesView

4.87 out of 5 average rating, 110 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

Immediate removal of stress at the front door. Being nestled in a marina’s serene waterfront & nature park is good for the soul. Relax in a jetted tub after a sun filled day & an al fresco meal on a back porch with charming outdoor dining. An open concept main level features large windows & comfortable seating through the entire property. 2 full bathrooms upstairs & a king sized bed provide maximum comfort & outdoor living on 2 balconies. Additional fees for pools, pets may apply.

Outdoor spacesWalkabilityDecor

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.

4.85 out of 5 average rating, 147 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*

PetsOutdoor spacesAmenities

A vibrant pot of red flowers is positioned in the foreground, with a wooden deck leading to a clear blue pool in the background. The pool area features a white fence and steps, surrounded by greenery and a cloudy sky above.

4.98 out of 5 average rating, 162 reviews

Stunning Bayview Home with Own Private Pool

This home can be occupied by a max of 12 adults with a total of 15 including children. Come relax in this gorgeous bay view single-family home in the lovely Caine's Woods neighborhood of Ocean City, adjacent to Fenwick Island. Imagine lazy days spent on the beach followed by a dip in the pool outside the kitchen door! GUESTS USE POOL AT THEIR OWN RISK! The pool is open from May 1- September 30. Obviously we can’t have it open during cold temperatures!

WalkabilityPetsSleep quality

Popular amenities for Ocean Pines pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

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, 212 reviews

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

Outdoor spacesPetsAmenities

4.86 out of 5 average rating, 212 reviews

The cottage exterior is seen with a large deck featuring white railings and a blue and white striped awning. A set of outdoor furniture is arranged on the deck, and steps lead down to a grassy area. The well-maintained, light-colored siding complements the serene environment.

Home in Fenwick Island

Hall Cottage, Fenwick Island, Delaware

PetsOutdoor spacesAccess

4.81 out of 5 average rating, 157 reviews

A cozy living area features a leather armchair positioned next to a small side table with a lamp. A storage chest rests on the floor beneath a collection of framed artworks and a flat-screen television, enhancing the eclectic atmosphere of the space.

Home in Berlin

Joy in the Morning @ Berlin Boho Bungalow

Outdoor spacesPetsNearby

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, 152 reviews

3 BR Waterfront Home, Minutes to the Beach

PetsWalkabilityComfort

4.94 out of 5 average rating, 126 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

WalkabilityPetsQuiet

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.

4.93 out of 5 average rating, 290 reviews

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

PetsOutdoor spacesNearby

5.0 out of 5 average rating, 10 reviews

Water's Edge Retreat OCMD

Outdoor spacesSleep qualityAir conditioning

A charming house with a light blue exterior is surrounded by lush greenery. A spacious deck features potted plants and outdoor seating. Colorful Adirondack chairs in red and blue are placed around a small fire pit on a patterned stone patio, inviting relaxation.

4.95 out of 5 average rating, 22 reviews

Cozy beach home away from home!

Outdoor spacesDecorKitchen

Pet-friendly home rentals with a pool

4.83 out of 5 average rating, 109 reviews

A sunny deck features white lounge chairs beside an above-ground pool. Lush greenery lines the background, providing a natural setting. A tall umbrella offers shade, and a potted plant adds a touch of greenery to the space.

Holiday home in Berlin

Berlin Beach House, near Ocean City & Assateague!

Outdoor spacesPetsLaundry

Holiday home in Ocean Pines

A spacious living area features a large sectional sofa adorned with decorative pillows. A ceiling fan provides airflow, while hardwood-style flooring complements the stylish furnishings. The open kitchen and dining area are visible in the background, creating a welcoming flow between spaces.

Bayside Blue Getaway near Ocean City

PetsOutdoor spacesAmenities

4.93 out of 5 average rating, 113 reviews

5.0 out of 5 average rating, 104 reviews

A spacious living room features two comfortable sofas arranged around a wooden coffee table. A flat-screen TV is mounted above a cozy gas fireplace. Natural light enters through multiple windows, while a dining area is visible in the background, furnished with a long table and chairs.

Home in Selbyville

Modern coastal beach home in West Fenwick Island

WalkabilityOutdoor spacesCheckout

4.98 out of 5 average rating, 105 reviews

A charming beach house is set on stilts, featuring a pink exterior with white shutters. The front porch offers a welcoming entry, surrounded by a landscaped yard with trees. Gravel driveway and a white picket fence enhance the appealing exterior in a tranquil neighborhood.

Home in Frankford

The Big Chill at Bethany Beach

WalkabilityOutdoor spacesAmenities

4.99 out of 5 average rating, 107 reviews

An expansive view of a sandy beach stretches along the coastline under a clear blue sky. Colorful umbrellas dot the shore, and the calm ocean appears in vibrant shades of blue, merging with the horizon in the background.

Apartment in Ocean City

Direct Oceanfront Newly Renovated W/ Pool 2 Bd

PetsOutdoor spacesPool

4.93 out of 5 average rating, 122 reviews

A large pool is framed by a wooden gazebo, offering shaded seating areas and views of tropical palm plants. The surrounding area features well-maintained landscaping and a spacious poolside deck, inviting relaxation in a serene environment.

Townhouse in Berlin

Bayside Townhouse w/ amazing amenities

Outdoor spacesPetsSleep quality

4.78 out of 5 average rating, 243 reviews

A private balcony features two turquoise adirondack chairs facing the ocean. The oceanfront view showcases the sandy beach and rolling waves, inviting moments of relaxation and enjoyment. A decorative 'Seaside' sign is displayed on the wall, enhancing the coastal ambiance.

Condo in Ocean City

DirectOceanFront on Boardwalk/Newly Remodeled/Pool

PetsOutdoor spacesBiking

4.88 out of 5 average rating, 114 reviews

Condo in Ocean City

Lovely Condo Steps 2Beach+Pool Unlimited Parking

WalkabilityPetsGetting around

Private, pet-friendly home rentals

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.

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

Outdoor spacesWalkabilityComfort

4.83 out of 5 average rating, 136 reviews

5.0 out of 5 average rating, 258 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

Hobbs & Rose | A Peaceful Cottage Escape

PetsWalkabilityHot tub

4.99 out of 5 average rating, 85 reviews

The exterior of the cottage is displayed, featuring a welcoming front porch with seating. Lush greenery surrounds the home, and a gravel pathway leads to the entrance. Large windows allow natural light, and a decorative plant is positioned near the entrance.

Cottage in Ocean Pines

3-bedroom cottage in Ocean Pines

Outdoor spacesWalkabilityNearby

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.

5.0 out of 5 average rating, 35 reviews

Waterfront Vacation Home in Ocean Pines

PetsWalkabilityHot tub

4.94 out of 5 average rating, 48 reviews

Offshore Tails-Relax with your pets near OCMD

WalkabilityPetsAccuracy

An open-concept living and dining area features a spacious sectional sofa with light blue accents and wooden coffee table. A dining table with six wooden chairs is set for a meal. The modern kitchen, equipped with stainless steel appliances, is visible in the background.

4.89 out of 5 average rating, 45 reviews

Ocean Parkway Retreat

Outdoor spacesWalkabilityQuiet

4.96 out of 5 average rating, 49 reviews

Home in Berlin

Cozy behind the Yellow Doors

Outdoor spacesPetsQuiet

An A-frame structure features large triangular windows inviting ample natural light. A spacious deck extends from the entrance, bordered by wooden railings. Surrounding trees provide a sense of privacy and tranquility. The modern design is complemented by a stone pathway leading to the entrance.