Holiday rentals with beach access 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, 46 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

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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

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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, 406 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!

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4.97 out of 5 average rating, 218 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

Water view at Ocean Pines Yacht Club 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

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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, 102 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.

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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, 140 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.

WalkabilityBeachAmenities

A modern living room features a comfortable sectional sofa in neutral tones, paired with a rustic wooden coffee table. A television is mounted above a stone accent wall. Glass doors open to a balcony, allowing natural light to fill the space.

4.95 out of 5 average rating, 127 reviews

Breezy Point #305 - Rooftop Deck Panoramic Sunsets

Welcome to Your Bayside Escape at Breezy Point! Step into style at this sleek bayside condo where modern comfort meets bayside views. Relax on the rooftop terrace and enjoy stunning sunset views and the fresh air. Tucked just off 28th Street, you're near restaurants, shops and quick bites. The boardwalk and beach are an easy walk or a quick drive away. A comfortable and convenient home base for couples and families. Hosting a bigger group? Ask about our other units in the same building!

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4.97 out of 5 average rating, 517 reviews

The living area features large sliding doors that open to a porch with stunning bay views during sunset. A neutral-colored couch and a cozy chair create a welcoming space. A wooden dining table complements the serene atmosphere, illuminated by the warm glow from the setting sun.

Townhouse in Ocean City

Edgewater Escape - Luxury Bayfront Loft with Porch

You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

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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, 137 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.

WalkabilityBeachWi-Fi

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, 140 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*

BeachWalkabilityDecor

4.96 out of 5 average rating, 202 reviews

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.

Home in Ocean City

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

PET FRIENDLY with fenced in yard, 2 blocks to the beach! 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!**

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An airy living space is highlighted by a high ceiling and large windows, inviting natural light. A gray sectional sofa faces a stone fireplace and a mounted television. Light blue cabinetry marks the kitchen area, with a dining table positioned nearby for flexibility.

5 out of 5 average rating, 16 reviews

Family Oasis - 4BR 3BA on Golf Course

TWO primary suites (4BR) and TWO living areas make this house double the fun! Our relaxed and beautiful home on a beautiful golf course is just 10 minutes from Ocean City. Enjoy all the amenities of Ocean Pines (pools, tennis courts, golf course, parks and walking trails). Parking for 6+ cars. House is loaded with well equipped spacious kitchen, great room with awesome entertainment setup, and tons of extra bedding options.

BeachLocationComfort

Popular amenities for Ocean Pines Accommodation with Beach Access

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

Superhost

The kitchen and dining area showcase a modern design with white cabinetry and stainless-steel appliances. A wooden dining table is surrounded by four white chairs. A cozy electric fireplace adds warmth to the space, which is illuminated by recessed lighting.

4.86 out of 5 average rating, 126 reviews

Rare Private Patio+Deck, Minutes Walk to OC Beach

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The kitchen area features a wooden countertop with a modern sink and stylish faucet. Shelves hold various glassware and dinnerware, while a spacious dining area is visible in the background, showcasing a large table surrounded by natural lighting.

5 out of 5 average rating, 37 reviews

Bayside Bungalow - Waterfront

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A modern living area features a spacious gray sofa and a wooden coffee table, complemented by a cozy area rug. Large glass doors open to a private oceanfront balcony, allowing natural light to fill the space. Decorative accents include a wall-mounted surfboard and a round mirror.

4.98 out of 5 average rating, 276 reviews

OceanFront-Fireplace-sleeps4-Balcony-King-Disney+

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5 out of 5 average rating, 29 reviews

Luxurious Ocean Block condo

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A bright living area showcases a large television mounted on a light-colored wall. A beige couch and cushions provide seating around a rectangular coffee table, which is adorned with decorative items. Floor-to-ceiling sliding glass doors offer unobstructed views of the ocean.

4.99 out of 5 average rating, 112 reviews

Stunning 3 Beds/2BA, Ocean Beachfront Condo

BeachWalkabilityComfort

A modern kitchen area is featured, with white cabinetry and a backsplash of stone tiles. A breakfast bar is recognized with high stools beside a wooden table. Natural light fills the space through a nearby door leading to a balcony.

4.92 out of 5 average rating, 37 reviews

Steps to sand and shops!

WalkabilityBeachLocation

A modern bedroom features a spacious bed with neutral bedding. A wooden accent wall adds texture, while a bright green plant wall enhances the decor. A desk and chair are positioned near a window, complemented by warm lighting from bedside lamps.

4.93 out of 5 average rating, 29 reviews

2Bed/2Bath/81st Street/Direct Bay Front/Pool

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A well-lit living area features a comfortable seating arrangement and a flat-screen TV mounted on the wall. Natural light floods in through sliding glass doors that open to a private balcony, enhancing the spacious feel of the room. A small table and plant add a touch of decor.

4.97 out of 5 average rating, 101 reviews

Oceanside Condo Steps From Beach

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Holiday House Rentals with beach access

A dining area displays a wooden table set for six, featuring white plates, silver cutlery, and sparkling glasses. A vibrant centerpiece of sunflowers and decorative pumpkins is placed on a bright red runner. The adjoining kitchen is visible, showcasing modern cabinetry.

4.97 out of 5 average rating, 65 reviews

Summer By The Sea

WalkabilityBeachOutdoor spaces

A light-colored home is featured, set against a backdrop of trees. The large front window allows natural light to enter the living space. A gravel driveway leads up to the entrance, with a small porch and railing providing access to the front door.

4.85 out of 5 average rating, 53 reviews

Amazing and peaceful family fun 4 bedroom home

BeachWalkabilityCondition

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

BeachConditionComfort

A charming two-story home is showcased, surrounded by lush greenery and tall trees. The exterior features a welcoming front porch with railings and a well-maintained driveway leading to the entrance. Sunlight filters through the leaves, creating a serene atmosphere.

5 out of 5 average rating, 7 reviews

Happy Tides Hideaway

BeachLocationAccuracy

The exterior of the waterfront home is shown, with a spacious deck and screened porch overlooking the water. Lush landscaping and a pathway lead to the dock, while large windows create a welcoming atmosphere. A patio umbrella provides shade for outdoor seating.

5 out of 5 average rating, 65 reviews

Ocean Pines, Waterfront Oasis

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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, 81 reviews

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

BeachLong stayParking

4.86 out of 5 average rating, 72 reviews

Ocean Pines Escape

BeachAccuracyDecor

The two-story waterfront home features a spacious exterior with a sloped roof and light-colored siding. A deck is visible at the back, accompanied by outdoor seating. The calm water reflects the bright blue sky, enhancing the serene riverside setting.

4.94 out of 5 average rating, 17 reviews

Waterfront 3BR | Private Dock + Views

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Holiday condos with beach access

A bright living area features a spacious blue couch paired with a light ottoman, accented by a patterned area rug. Large windows with sheer curtains allow natural light to fill the space, while a wall-mounted TV and decorative shelving complete the welcoming atmosphere.

4.97 out of 5 average rating, 197 reviews

Family Condo Oceanside in Midtown OC

BeachWalkabilityNearby

A comfortably arranged living area features a light-colored sofa adorned with decorative pillows. A soft ottoman rests in front, and a wall-mounted artwork depicts a serene seascape. Natural light filters in through sheer curtains, while a modern lamp and a fan enhance the space.

4.99 out of 5 average rating, 106 reviews

Ocean block condo

ViewBeachAmenities

A modern kitchen is displayed with white cabinetry and granite countertops. An L-shaped island with four chrome swivel stools offers additional seating. Stainless steel appliances, including a microwave and refrigerator, complement the space. A window provides a view of the water outside.

4.97 out of 5 average rating, 101 reviews

Completely Renovated Luxury Bay Front Condo

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A vibrant neon sign reading 'Sea Glass Sunrise' is framed by lush green foliage, set against a backdrop of a serene beach at dawn. The soft pastel colors of the sky create a peaceful atmosphere, enhancing the welcoming ambiance of the space.

4.99 out of 5 average rating, 133 reviews

Gorgeous Beachfront! King Bed, Direct Ocean View!

ViewWalkabilityKitchen

An open-concept living area showcases a spacious sofa arranged around a light-colored coffee table, accented with decorative shells. A dining area with white bar stools and a fully equipped kitchen are visible in the background, along with coastal-themed decor and soft natural light.

4.98 out of 5 average rating, 116 reviews

Oceanside Charm, desirable midtown Ocean City, MD

BeachViewCondition

The living room showcases a comfortable sofa facing a large television. A round coffee table sits in front, and a ceiling fan provides gentle airflow. Sliding glass doors open to a scenic waterfront view, allowing natural light to fill the space.

4.99 out of 5 average rating, 135 reviews

The Hideaway By The Bay OCMD

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4.91 out of 5 average rating, 142 reviews

Cozy Beach Front Condo with Modern Amenities.

BeachViewAccuracy

The living area features soft blue furnishings and a light wood coffee table. Floor-to-ceiling windows offer direct views of the ocean, while two lamps provide warm lighting. A coastal-themed artwork adorns the wall, enhancing the serene atmosphere of the space.