Waterfront holiday rentals in Ocean Pines

4.94 out of 5 average rating, 287 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!

BeachViewIndoor spaces

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.

5.0 out of 5 average rating, 117 reviews

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!

BeachViewLocation

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, 149 reviews

Gorgeous Beachfront! King Bed, Direct Ocean View!

Stunning beachfront condo with direct view of the ocean! Your vacation home away from home! Everything you need right ON the beach. All linens, supplies and a well-stocked kitchen! New 65" TV w/free 4K Netflix provided! Modern serene decor in the heart of OC! Feel like getting out? Enjoy walking distance to Seacrets, Mackey's, and Fager's Island, Subway, Candy Kitchen or Dumsers' Dairyland! More adventure? Walk to minigolf, pontoon boats and jetski rentals! Only 4 minute drive to the boardwalk!!

BeachViewValue

4.93 out of 5 average rating, 149 reviews

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.

Home in Ocean City

3 BR Waterfront Home, Minutes to the Beach

Recently updated waterfront house located in the family-friendly Montego Bay community. Enjoy beautiful sunsets on the back deck or hop in one of the kayaks for a paddle around the wide-open canal. Try your hand at crabbing or fishing off the dock to catch your dinner. Within easy walking distance of the beach and Northside Park (about 10 minutes walk to both). Beach chairs, toys, boogie boards, and umbrellas are yours to use for fun in the sand and surf. The dock is available for boat tie-ups.

ViewBeachDecor

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.

4.99 out of 5 average rating, 105 reviews

Direct Oceanfront Newly Renovated W/ Pool 2 Bd

A slice of paradise on the 18th floor! This fully renovated beachfront condo boasts breathtaking views of the glistening ocean. With two bedrooms and two modern baths, this haven offers the perfect blend of luxury and comfort. Imagine waking up to the sound of waves crashing and sipping your morning coffee overlooking the endless horizon. Whether you're lounging by the shimmering pool or strolling along the pristine shoreline, every moment here is infused with the tranquility of coastal living.

BeachViewWalkability

Guest suite in Ocean Pines

4.95 out of 5 average rating, 419 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!

ViewBeachSleep quality

4.97 out of 5 average rating, 223 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

BeachViewCheck-in

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, 210 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!

BeachViewHeating

A panoramic view of the ocean is visible, with gentle waves lapping at the sandy beach. Below, an outdoor pool is surrounded by lounge chairs and clear pathways, providing a peaceful atmosphere. Skies are blue, enhancing the serene coastal setting.

4.88 out of 5 average rating, 142 reviews

Oceanfront Condo w/ Resort Amenities 3BDR &3pools

Sea Watch Condo's is an ideal family location with tons of amenities. The until is a recently updated 3 bedroom 2 bathroom condo that sleeps 6 people in 2 queen beds, 2 twin beds . The unit is ocean front with a large oceanfront balcony. The amenities Include, basketball court, tennis courts, playground, arcade, movie theater, billiard room, indoor pool and outdoor pool as well as a restaurant. The condo has 24 hour security and plenty of parking. Pools closed in off season

ViewBeachKitchen

4.91 out of 5 average rating, 294 reviews

A spacious living area features a large sectional sofa and two armchairs, complemented by a coffee table and area rug. Natural light floods through sliding glass doors that lead to a private deck, with water views visible from the room. Decorative wall art adds a calming touch.

Townhouse in Ocean City

Bayfront Townhouse: Fishing, Sunsets & Family Fun!

Escape to this stunning, updated bayfront townhouse in midtown Ocean City! Featuring 3 bedrooms with 3 ensuite bathrooms, enjoy breathtaking sunsets from your private deck. This entertainer's dream offers a spacious open layout with a gourmet kitchen and waterfall countertops. Benefit from two assigned parking spots, fish directly off the back deck pier, a local favorite fishing spots, you'll love the waterfront access and relaxing atmosphere.

BeachViewComfort

5.0 out of 5 average rating, 125 reviews

A wooden dock extends over calm water, surrounded by tall trees. A pair of Adirondack chairs provide a peaceful spot to enjoy morning sunlight filtering through leaves, creating a serene atmosphere perfect for relaxation.

Home in Newark

Secluded Waterfront - Beach 15mi, Kayaks, Firepit

Casa Blue Heron is a 2,254 ft² (209 m²) custom waterfront home with a private dock, firepit, and water views throughout - nestled on a tidal inlet connected to Chincoteague Bay - and near Assateague, Berlin, Ocean City, Snow Hill, and much more. ★ "A private and tranquil setting where it is impossible not to relax and appreciate nature… Wish I had booked an extra day!" Add us to your wish list by clicking the ❤️ in the upper-right corner.

BeachRiverSleep quality

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, 146 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

ViewRiverTV

Popular amenities for Ocean Pines waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

A cozy private balcony features a woven seating area with a sofa and two chairs, surrounded by greenery. A small coffee table sits in front, with a potted plant placed atop. The wall displays the phrase 'good vibes', adding a cheerful touch.

4.95 out of 5 average rating, 114 reviews

Studio Charm w/ Deck: Walk to Beach & Dining!

ViewBeachCondition

Superhost

4.84 out of 5 average rating, 173 reviews

Amazing oceanfront view 3 blocks from boardwalk

BeachViewValue

The image features a view from the balcony showcasing the beach and Atlantic Ocean. Clear skies with scattered clouds are visible, while the sandy beach is framed by a wooden fence. Two lounge chairs are placed on the balcony, offering a relaxed seating area.

4.94 out of 5 average rating, 107 reviews

Direct Oceanfront 3BR/2 Kings, Great for Families!

BeachViewAmenities

5.0 out of 5 average rating, 8 reviews

Lookout View | Bayfront, Beach Gear & Family Stay

ViewBeachKitchen

5.0 out of 5 average rating, 12 reviews

Bright, Updated Condo, Pool, Convention Center

BeachViewNearby

An open floor plan is showcased, featuring a modern kitchen with a central island and white cabinetry. Large sliding glass doors allow for natural light and ocean views. A cozy seating area includes a coffee table and comfortable blue couches, inviting relaxation in a bright environment.

5.0 out of 5 average rating, 10 reviews

NEW: Oceanfront End-Unit Condo w/ 100ft Balcony

ViewBeachKitchen

4.93 out of 5 average rating, 14 reviews

Bayfront Escape w/Stunning Sunsets & Private Dock

ViewBeachDecor

A bright bedroom features floor-to-ceiling windows providing panoramic ocean views. A queen bed is centered against a light-colored wall, complemented by a patterned quilt. A dresser and wall-mounted television complete the space, with natural light illuminating the calming atmosphere.

5.0 out of 5 average rating, 67 reviews

SuperHost! Amazing OceanFront View with 2 Pools!

BeachViewHospitality

Waterfront house rentals

4.89 out of 5 average rating, 155 reviews

Two large windows frame the expansive ocean view, providing natural light to the living space. The scene features sandy beach dunes leading towards the water, where the calm blue ocean meets the clear sky.

Home in Ocean City

Closest condo to the beach in OC! Dog Friendly!

ViewBeachOutdoor spaces

5.0 out of 5 average rating, 8 reviews

Water's Edge Retreat OCMD

BeachOutdoor spacesSleep quality

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.

4.96 out of 5 average rating, 24 reviews

Waterfront 3BR | Private Dock + Views

BeachViewCleanliness

A waterfront home is surrounded by green lawns and trees, featuring multiple outdoor seating areas. The spacious deck overlooks the water and is equipped with a gas grill. A dock is visible, allowing for easy access to the bay.

5.0 out of 5 average rating, 64 reviews

Waterfront w/Dock, Rooftop Terrace & 2 Kings

BeachViewIndoor spaces

4.98 out of 5 average rating, 42 reviews

WHAT DAY IS IT???????

BeachViewFamily

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.

4.81 out of 5 average rating, 21 reviews

Ocean City Waterfront Home with Skyline Views!

BeachViewWalkability

5.0 out of 5 average rating, 18 reviews

Fabulous Waterfront Getaway with Sunsets & Eagles

BeachViewLocation

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, 31 reviews

Waterfront Vacation Home in Ocean Pines

BeachViewBathroom

Waterfront condo accommodation

Superhost

The kitchen area features modern appliances and sleek cabinetry with a butcher block countertop. Two bar stools are positioned at the counter, creating a casual dining space. A cozy seating arrangement is nearby, complemented by a small table lamp and decorative elements.

4.87 out of 5 average rating, 118 reviews

Cozy beach side condo

BeachViewAccuracy

4.83 out of 5 average rating, 250 reviews

Beachfront with a View and Amenities Galore

BeachViewLayout

An oversized balcony features comfortable seating with deep blue cushions. A glass-top table sits between the chairs. Below, the water view showcases boat traffic, while string lights add a gentle ambiance. The surrounding area includes other residential units and docks.

4.88 out of 5 average rating, 276 reviews

Bayside Retreat in the Heart of Ocean City!

BeachViewBiking

A pair of blue Adirondack chairs are positioned at a small table on a balcony overlooking the ocean. The expansive view of the sandy beach and distant umbrellas is visible, creating a serene spot for relaxation.

4.96 out of 5 average rating, 239 reviews

Luxury Oceanfront Escape!

BeachViewLong stay

Superhost

A primary bedroom is presented with a spacious bed topped with neutral linens. Floor-to-ceiling windows frame a serene ocean view. Natural light is allowed to fill the room, accentuated by light wood paneling. A bedside table features a lamp, and a comfortable chair is placed nearby.

4.87 out of 5 average rating, 182 reviews

2 BdrmOceanfront-Pool, Xbox, Pickleball, Gym, WiFi

ViewBeachCleanliness

A cozy living area displays a light blue color scheme. A white sofa is positioned beside a coffee table on a patterned rug, while a dining table is set nearby. Floor-to-ceiling sliding doors open to a balcony, offering views of the ocean.

4.96 out of 5 average rating, 321 reviews

Caramar Couples Retreat

BeachViewComfort

Two chairs are positioned beside a small round table, offering a serene view of the ocean through large windows. The sandy beach stretches out beneath a cloudy sky, with gentle waves lapping at the shore.

4.98 out of 5 average rating, 133 reviews

Ocean front condo with Balcony

BeachViewIndoor spaces

A spacious living area features a cozy arrangement of seating with patterned upholstery and soft textures. A circular coffee table is centered amidst the furniture, and a wall-mounted television is paired with a stone accent wall. Large sliding doors open to the private balcony.