House holiday rentals in Ocean Pines

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, 45 reviews

Tranquil Waters, OceanPines, 3 br, Dog Friendly

Peaceful Coastal Getaway – Dog Friendly! Relax with the whole family at this peaceful beach retreat! This 1,500 sq. ft. home away from home is perfect for a laid-back vacation near the shore. Featuring 3 bedrooms (King, Queen, and 2 Twins), this home is spotlessly disinfected before each stay and includes a full linen package for your comfort and convenience. Enjoy a free parking pass to the Ocean Pines Beach Club on 49th Street, and make the most of the beautiful outdoor space—a low fenced-i

A scenic collage features various images: a tranquil beach sunset, a lush golf green with a white sand trap, a wooden pier stretching over gentle waves, wild horses running along the shore, and a charming screened porch nestled among tall trees.

4.97 out of 5 average rating, 61 reviews

Ocean Pines-OCMD Bliss at the Beach- Sat. to Sat.

Welcome to Bliss at the Beach, our charming 3br, 2ba home nestled in the desirable, beloved Ocean Pines community. Loved for its safe, quaint, family friendly neighborhoods. Find yourself less than 15 minutes away from the beautiful beaches and vibrant shopping, dining and boardwalk district of Ocean City. Enjoy the ease of the prepaid parking at the Ocean Pines Beach club on 49th street, just unload the family and walk on the beach!! Summer months Bliss is a 7-night minimum to guests 25+older

An A-frame structure is set amidst lush greenery, featuring a welcoming front porch with steps leading up to the entrance. Two bicycles are positioned nearby, and vibrant flowers adorn the edges. Sunlight filters through the leafy trees, enhancing the natural surroundings.

5 out of 5 average rating, 52 reviews

hi-A-tus A-frame

Charming A-frame nestled in the heart of OP. Open floor plan, softest sheets, flat screen TVs, high speed WiFi, in an amenity filled community surrounded by multiple beaches. 10 min from OC & 15 min from Assateague! Sleeps 4 comfortably. Perf for 4 adults or fam. Must be 25 yrs old. Enjoy all that OP has to offer including 5 pools, multiple playgrounds, yacht club & farmers market. Weekly rental during the high season (6/6 - 8/29), Sat check-in/Sat check-out only! If you book diff, we'll cancel

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, 100 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.

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, 142 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!

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.

Superhost

5 out of 5 average rating, 3 reviews

Birdies by the Bay | Waterfront & Private Dock

Welcome to Birdies by the Bay! This newly remodeled 3-bedroom, 2-bath waterfront home sleeps 6 with a king and two queens. Enjoy an open layout, a sunny water-view room, and a deck with seating, a grill, and a private dock overlooking the 3rd Green of the golf course. Nearly everything’s new—just the stall showers kept their charm. Perfect for families, couples, or small group getaways in beautiful Ocean Pines!**** Must be 25 years or older to reserve this property. Please See rules.****

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.

4.91 out of 5 average rating, 199 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!

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, 14 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.

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, 139 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 cozy living area presents a light brown couch adorned with colorful cushions and a decorative throw. Two accent chairs sit across from the couch, positioned on a patterned area rug. Natural light filters through sheer curtains covering a large window, illuminating the space.

4.97 out of 5 average rating, 105 reviews

Sweet Retreat

Sweet Retreat is conveniently located in Ocean Pines, Maryland. The premiere residential and resort community of Ocean Pines is located eight miles inland from the ocean resort town of Ocean City. Ocean Pines has over 9 miles of waterfront property and 3,000 acres of wooded areas. Community amenities include beaches, a yacht club, golf course, community center, a Beach Club Pool and other community pools. Passes are available at ocean Pines Association.

A charming house with large windows is situated by the water, framed by lush greenery. A wooden dock leads from the house to the water's edge, surrounded by tall grass. Soft evening light highlights the structure, creating a serene ambiance.

4.99 out of 5 average rating, 140 reviews

Charming Waterfront Cottage w/2 King Suites + Dock

Newly renovated, sparkling, spacious house with room for seven and waterfront views is waiting for you. Perfect for a single or double family getaway, girls weekend, or quiet retreat. *Please note this is a No Smoking and No Pet Property. **We are located in a quiet, residential neighborhood with lovely neighbors in close proximity. Please consider this when booking. ***We do not supply sheets and towels. Rental License #2162

Popular amenities for Ocean Pines house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A welcoming living room features a cozy sofa and two armchairs arranged around a circular coffee table. A flat-screen TV is mounted above a fireplace, while a decorative area rug with floral patterns adds warmth to the space. Natural light streams through sheer curtains.

4.95 out of 5 average rating, 78 reviews

Cozy home in Ocean Pines

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.

4.94 out of 5 average rating, 283 reviews

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

4.93 out of 5 average rating, 15 reviews

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

A family-friendly home is nestled among trees, featuring a cozy outdoor area with a hammock and fire pit. The interior includes a spacious living room with a Smart TV and a welcoming layout that captures natural light, presenting a relaxing environment for guests.

5 out of 5 average rating, 58 reviews

Ocean Pines Fun – Arcade, Pools & Near O.C. Beach

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.

4.96 out of 5 average rating, 46 reviews

Beautiful Spacious 4 Bedroom Home in Ocean Pines

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.

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.

A converted garage features a game room setup with a pool table and a dart board on the wall. Light filters through the windows, illuminating the patterned rugs on the floor. Two folding tables are positioned, awaiting use for gatherings or games.

4.9 out of 5 average rating, 63 reviews

Private, pet-friendly, w/game room & new kitchen

Weekly house rentals

5 out of 5 average rating, 42 reviews

Bayside - Waterfront - Dock - Quiet Area

A deck with a metal table and chairs overlooks a serene canal. Boats are docked nearby, while charming homes line the opposite bank, surrounded by lush trees. The clear blue sky reflects the tranquil atmosphere of the waterfront setting.

4.97 out of 5 average rating, 38 reviews

WHAT DAY IS IT???????

Superhost

A circular wooden deck overlooks tranquil waterfront views, featuring a mix of green grass and trees. Comfortable seating is positioned on the deck, allowing for relaxation while enjoying the serene surroundings. A two-story home and docks are visible in the background.

4.8 out of 5 average rating, 15 reviews

Oceans End Waterfront Retreat

The waterfront home is positioned along the canal, featuring a spacious deck with seating areas and landscaping. A stone pathway leads to the dock, which is equipped for boating. The exterior is complemented by greenery and a calm water view, providing a serene outdoor setting.

4.81 out of 5 average rating, 26 reviews

Waterfront Retreat with Boat Dock

A single-story house is positioned among tall trees, showcasing a welcoming front porch with steps leading to a paved driveway. Surrounding landscaping includes trimmed bushes and grassy areas, creating a natural setting that fosters a sense of privacy.

4.95 out of 5 average rating, 38 reviews

Beachin' it in Ocean Pines

4.86 out of 5 average rating, 71 reviews

Ocean Pines Escape

A spacious living area is outlined by an inviting sectional sofa adorned with cushions. A coffee table is centered on a geometric rug, while a fan hangs from the ceiling. Light floods in through a skylight, illuminating the adjacent kitchen area with dining seating.

5 out of 5 average rating, 17 reviews

Cozy home minutes from golf, parks, beach and more

A spacious living room features light-colored furniture with striped patterns, complemented by a neutral decor. A modern fireplace is set beneath a wall-mounted television, and the kitchen area is visible, showcasing cabinetry and a decorative anchor. Natural light flows through sliding doors leading to a balcony.

4.98 out of 5 average rating, 61 reviews

Luxurious Bay Front Condo

Private house rentals

5 out of 5 average rating, 5 reviews

Sandbar Coastal Retreat near Ocean City

The front exterior of the house features a yellow facade with large windows and a welcoming doorway. A wooden deck is accessed by a set of stairs, and outdoor chairs are positioned for seating. Surrounding trees indicate a natural, wooded setting.

4.95 out of 5 average rating, 41 reviews

Salty Serenity

4.96 out of 5 average rating, 96 reviews

A barn-style exterior of the condo is showcased, featuring a metal roof and three large garage doors at ground level. The second floor includes a deck with an entrance door. Expansive green space surrounds the property, with trees visible in the background under a clear blue sky.

Home in Berlin

SpaciousCondo nearOcean City|Winery|Golf on 5Acres

The cottage exterior is framed by tall trees, showcasing a welcoming entrance with a deck and steps leading up to a door. The light-colored siding and contrasting teal door create a fresh appearance. Surrounding landscaping includes a gravel path and shrubs, providing a natural setting.

4.82 out of 5 average rating, 143 reviews

122 Ocean Parkway, Ocean Pines, MD

An open living area is presented, featuring a spacious sectional sofa, a light wood dining table with seating for six, and a modern kitchen. Natural light floods the space through large windows, enhancing the neutral color palette and warm wood accents.

5 out of 5 average rating, 17 reviews

House with Fire Pit + Private Yard near Ocean City

A spacious living area features a soft sectional sofa, positioned for cozy relaxation. A gas fireplace, framed by a white mantel, adds a warm touch. A smart TV is mounted on the wall, and a glass door leads to a dining area with natural light.

4.89 out of 5 average rating, 37 reviews

Serene OP cottage perfect for families!

Colorful armchairs with a fish pattern provide comfortable seating by large windows that offer views of the water and surrounding nature. A small green side table stands between the chairs, adorned with a vase of flowers.