Family-friendly vacation rentals in Ocean Pines

4.94 out of 5 average rating, 278 reviews

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.

Home in Ocean City

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, 190 reviews

A single-story home sits nestled among lush greenery, featuring a welcoming front porch with a wooden railing. A set of steps leads up to the entrance, flanked by large windows adorned with green shutters, complementing the home's neutral exterior.

Cottage in Ocean Pines

Cozy Beach Getaway in the Lovely Ocean Pines North

Welcome to our Cozy Beach Getaway!! ☀️🌊👙⛱️🐚🏖️🌞🌅⛅️ This beautiful and peaceful home is located in Ocean Pines North. 3 bedrooms, 2 bathrooms. Peaceful front porch and back deck. 🏡🏝️ Whether you’re looking for a summer family vacation, girls weekend getaway, or just a break from reality, this is the perfect place! Washer/dryer 🧺, two smart TV’s 📺, driveway fits 4 cars comfortably 🚗. Enjoy the hustling city of Ocean City during the day and stay in the tranquility and peaceful Ocean Pines at night! 🏖️💞☀️

5 out of 5 average rating, 18 reviews

Whimsical Willow w/ Beach Club Pass and No Pet Fee

Discover this charming 3-bedroom home! With wood floors throughout, it features a king master suite, a queen bedroom, and a kids’ room with a twin-over-full bunk. Enjoy a fully stocked kitchen, fast WiFi, a screened-in porch, and a jetted tub for ultimate relaxation. Perfect for families or dual-family stays! Explore Ocean Pines or take a quick 10-minute drive to Ocean City for endless fun. Included is the Beach Club Parking Pass! Plus- A local manager is here to ensure everything goes smoothly.

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, 396 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!

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, 73 reviews

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

Have fun with the whole family at our stylish Ocean City-convenient home! This wooded beach house boasts many modern upgrades including a beautiful kitchen with gas range, large flat panel televisions in almost every room, a washer and dryer, and even a Wii video game system in the living room! Queens in 3 bedrooms and a bunk bed with trundle in the 4th! Finally, enjoy all the amenities of Ocean Pines including access to 5 pools, a private OC beach club (w/pool!), and much more! Lic. No. 4586

4.97 out of 5 average rating, 206 reviews

A serene waterfront scene is captured at sunset, with vibrant colors reflected in the calm water. A charming building with large windows is illuminated, surrounded by lush trees, and boats are docked along the waterfront, creating a peaceful atmosphere.

Condo in Ocean Pines

Ocean Pines marina view condo

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

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.

4.98 out of 5 average rating, 138 reviews

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!

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.

An open-concept living area features a well-equipped kitchen with modern appliances and a dining table surrounded by blue chairs. A spacious seating area is visible, leading to a staircase that ascends to an upper loft with a railing overlooking the main level.

4.96 out of 5 average rating, 117 reviews

Newly Renovated Ocean Pines Cottage

Completely remodeled beach home with brand new furnishings in Ocean Pines. Open concept living on main level with beautiful well-equipped kitchen, seating for 10 total at island/dining table and a relaxing living room. Off the hallway is the king bedroom and separate full bathroom with bathtub. Spacious mud/laundry room with beach chairs, umbrella and wagon available for use. Open loft area upstairs with arcade game, lounging area, 2 additional bedrooms and full bath with stand-up shower.

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, 116 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!

Guest suite in Ocean Pines

A bright, open kitchen area is visible, featuring modern appliances and a spacious countertop. Large windows allow natural light to fill the room. A comfortable chair sits beside a decorative rug, while a sleek ceiling fan contributes to the airy atmosphere.

4.99 out of 5 average rating, 135 reviews

Newly built bright and airy guest suite!!!!

FREE oceanfront parking pass with bookings. 2nd floor private suite with parking, patio/firepit, and self check-in private entry. We are located just minutes from the Ocean City beaches, quaint small town of Berlin, Ocean Downs Casino, Assateague, Windmill Creek Winery, restaurants, and outlets. Enjoy neighborhood amenities such as a waterfront Yacht Club with restaurant and live music (seasonal), golf, farm market, playgrounds, 5 pools/fee, (no pool on property) racquet club.

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.

5 out of 5 average rating, 12 reviews

Cozy beach home away from home!

Welcome! Come enjoy a cozy experience at this centrally located home in the desired Ocean Pines Community! This home is near the playground and allows access to the on-site golf course, five pools (including indoor pool!) tennis courts, and marina for a small fee. Fun in the sun awaits 15 minutes away in downtown Ocean City, where you can stroll the boardwalk, lounge on the sand, or hit the amusement park. Plenty of restaurants, grocery stores and shopping within 15 minutes.

Popular amenities for Ocean Pines family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

An aerial view of a spacious waterfront property showcases a well-manicured yard with a private boat dock. The surrounding neighborhood is visible, featuring a variety of homes, some with outdoor amenities like pools and decks. The serene bay can be seen in the background.

4.79 out of 5 average rating, 14 reviews

Ocean City Waterfront Home with Skyline Views!

4.93 out of 5 average rating, 158 reviews

A spacious living area features a large sectional sofa adorned with blue accent pillows. Exposed wooden beams grace the ceiling, while a light wooden floor complements the dark furnishings. A coffee table sits centrally, and a modern kitchen can be seen in the background.

Townhouse in Ocean City

Beach, Boardwalk n Fun- just steps to the beach

Apartment in Bethany Beach

An airy living space is presented from an aerial perspective, featuring two patterned sofas facing a light-colored coffee table. A television is positioned on a cabinet against one wall, with natural light filtered through sheer curtains enhancing the open feel of the room.

4.88 out of 5 average rating, 148 reviews

Sea Colony Beach And Tennis Resort

4.89 out of 5 average rating, 100 reviews

A bright living area features blue walls complemented by light-colored furniture. Two sofas are positioned around a centrally placed coffee table, which holds decorative items. Large glass sliding doors open to a balcony, allowing natural light to fill the space.

Condo in Ocean City

Updated Mid- Town Condo at Ocean City Beach!

4.76 out of 5 average rating, 107 reviews

An aerial view showcases a large swimming pool area surrounded by lounge chairs and umbrellas, with a smaller kids' pool adjacent. Tennis courts and well-maintained landscaping are visible, alongside additional buildings and open green spaces in the distance.

Townhouse in Selbyville

Bayside - Best Deal in Bayside!

4.96 out of 5 average rating, 26 reviews

Home in Berlin

White Marlin Cottage>HOT TUB<

4.94 out of 5 average rating, 143 reviews

The beachfront property is displayed, featuring a modern four-story structure with multiple balconies. Soft sandy pathways lead to the building, bordered by natural grasses and low fencing. Clear blue skies enhance the oceanfront setting.

Condo in Ocean City

Direct Ocean Front/Gorgeous Views/Indoor Pool

4.92 out of 5 average rating, 235 reviews

A serene view captures a group of ducks swimming in a calm waterway, bordered by lush green grass and small reeds. The surrounding area features a natural landscape, with distant homes visible in the background.

Townhouse in Selbyville

Beach house on lake!

Family- and pet-friendly home rentals

A charming cottage exterior is showcased, featuring a distinctive A-frame design. The front porch is framed by wooden railings, while a path of stepping stones leads to the entrance. Surrounding trees provide a natural backdrop, enhancing the serene outdoor environment.

5 out of 5 average rating, 23 reviews

Ocean Pines 2BR 1BA Cottage with Fire Pit

4.91 out of 5 average rating, 120 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

4.95 out of 5 average rating, 151 reviews

The interior of the bus features a cozy layout with wood paneling and large windows providing natural light. A comfortable seating area, equipped with pillows, is situated next to a compact kitchen with a stove and cabinets. A small dining table with two placemats is visible.

Bus in Frankford

Delightful Skoolie Near Bethany Beach

4.94 out of 5 average rating, 149 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

5 out of 5 average rating, 218 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

4.82 out of 5 average rating, 140 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

4.95 out of 5 average rating, 151 reviews

The exterior of a two-story house is displayed, featuring a wraparound porch and a driveway surrounded by trees. A garage is visible on the left side, and the front yard is landscaped with grass and stone pathways.

Guest suite in Frankford

Quiet setting on private pond among the wildlife

4.89 out of 5 average rating, 38 reviews

Cozy Stay by the Bay

Family-friendly home rentals with a pool

4.93 out of 5 average rating, 14 reviews

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

A modern two-story home is situated on a tree-lined lot, featuring a welcoming front entrance. Brightly colored adirondack chairs provide seating in the gravel area by the driveway, which accommodates several vehicles. Natural light filters through the trees, creating a serene environment.

4.95 out of 5 average rating, 42 reviews

Beautiful Spacious 4 Bedroom Home in Ocean Pines

4.91 out of 5 average rating, 92 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

A spacious sectional sofa occupies a corner of the living room, adorned with decorative pillows featuring ocean-themed designs. Soft, neutral-colored walls enhance the airy feel of the space, while sunlight filters through the nearby windows, creating a bright and inviting environment.

4.88 out of 5 average rating, 41 reviews

Charming cul-de-sac House just minutes from OC.

5 out of 5 average rating, 5 reviews

Home in Berlin

Ocean City Escape. Spacious Home. Pool & Golf

The exterior of the home features a welcoming entrance with a covered porch and decorative seasonal wreath. A stone pathway leads to the front door, surrounded by lush plants and landscaping, framed by light-colored siding and a garage door.

4.96 out of 5 average rating, 26 reviews

Robin Hood Retreat

4.86 out of 5 average rating, 7 reviews

The Whale’s Tale Retreat w/ Beach Club Pass

A pair of teal Adirondack chairs sits on a wooden dock overlooking calm water. Decorative pillows add a touch of comfort. Boat slips are visible in the background, with a soft reflection on the water's surface as the sun sets behind scattered clouds.