House holiday rentals in Ocean Pines

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, 66 reviews

Ocean Pines, Waterfront Oasis

Beautiful waterfront home! Park two boats. "Endless Summer" is on the canal. Located on the St Martins River in Ocean Pines. Centrally located, close to downtown Ocean City, MD, "the boardwalk", bustling West OC and historic Berlin, MD. Explore Assateague Island, Del. beaches, all just a short drive in the amenity filled [pools, golf, pickle ball, tennis, trails and parks] OP community. Linens, cleaning team & beach club parking included. Must be 25 or older or military service. No pets.

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

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

5 out of 5 average rating, 21 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.

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, 75 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.

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, 140 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.

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, 118 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!

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.

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, 137 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 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, 64 reviews

Summer By The Sea

Located on a quiet cul de sac, this cute 3 bedroom home is a perfect getaway. Enjoy the fun and excitement of Ocean City with its beach, boardwalk, restaurants and nightlife, and then retreat to the quiet relaxation of Ocean Pines. A movie theater, outlets, and fabulous eateries in West OC. Assateague Island National Seashore is only minutes away. Ocean Pines offers a state of the art public golf course, pool access(for a fee ) playgrounds, and beach club .

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.

The bright living room features large windows overlooking the river, allowing natural light to fill the space. Comfortable seating arrangements are present, with patterned sofas and a wooden coffee table at the center. A television stands beside a cozy fireplace, enhancing the inviting ambiance.

5 out of 5 average rating, 9 reviews

Riverside Retreat- 3 Story/Direct Waterfront

This spacious three-story residence features 4 bedrooms and 2.5 bathrooms, including a king bedroom with an en-suite bath & balcony. Enjoy an open kitchen, dining area, and a stunning living room with river views. The backyard offers a private "beach" with Adirondack chairs and picnic tables. Just 20 minutes from Ocean City’s shopping, dining, and beaches. Perfect for family fun and relaxation! A local manager is here to ensure everything goes smoothly

Popular amenities for house rentals in Ocean Pines

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

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!

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, 39 reviews

Salty Serenity

A bright living area features a comfortable blue sofa and an armchair, with a decorative lamp beside them. A white coffee table sits atop a patterned rug, which complements the room's light decor. Two windows, adorned with blinds, allow natural light to filter in.

5 out of 5 average rating, 18 reviews

Stubbe's Beach House, Home in Ocean Pines, MD

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, 279 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

5 out of 5 average rating, 58 reviews

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

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.

Superhost

4.89 out of 5 average rating, 38 reviews

Cozy Stay by the Bay

Weekly house rentals

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, 52 reviews

Amazing and peaceful family fun 4 bedroom home

4.95 out of 5 average rating, 88 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

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???????

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

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.

4.79 out of 5 average rating, 14 reviews

Oceans End Waterfront Retreat

The open-concept living room features two dark sofas adorned with decorative pillows, centered around a round coffee table. Bright overhead lighting illuminates the space, which leads into a modern kitchen visible in the background, creating a welcoming and functional gathering area.

4.98 out of 5 average rating, 61 reviews

Cozy home 8 miles from OCMD *Beach Pass Included*

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

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, 21 reviews

Villa Caribbean OCMD

Private house rentals

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, 76 reviews

Cozy home in Ocean Pines

A light grey two-story house features a large front porch with white railings and multiple seating areas. Bright turquoise shutters frame the windows, and an American flag is displayed on the porch. Lush green landscaping complements the inviting facade.

4.94 out of 5 average rating, 52 reviews

West OC Bayside Getaway w/ pool

5 out of 5 average rating, 31 reviews

A spacious living room features a large brown sectional sofa adorned with colorful throw pillows. A round coffee table sits in the center, surrounded by a light-colored woven rug. Natural light floods the space from multiple windows, highlighting the decorative wall mirrors and neutral tones.

Home in Berlin

Cottage on Snug Harbor with hot tub!

An aerial view showcases a peaceful neighborhood surrounded by lush greenery. Various homes with distinct roofs line the streets, with some featuring boat docks alongside calm waters. The layout reflects a family-friendly area characterized by low traffic and inviting outdoor spaces.

5 out of 5 average rating, 40 reviews

Bayside - Waterfront - Dock - Quiet Area

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.

4.8 out of 5 average rating, 46 reviews

The Oliver House

4.96 out of 5 average rating, 27 reviews

Home in Berlin

White Marlin Cottage>HOT TUB<

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.