Waterfront holiday rentals 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, 264 reviews

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!

The living area features comfortable electric reclining sofas facing a coffee table. Large windows provide views of the ocean, while a dining area and modern kitchen are visible in the background, creating a spacious and inviting atmosphere.

5 out of 5 average rating, 116 reviews

2BRCapri: Indoor Pool, Game Room, Massage Chair

ALL THE COMFORTS OF HOME AT THE BEACH! BRAND NEW RENOVATED BATHROOMS! -ALL LINENS INCLUDED -Comfortable electric-reclining sofas -65-in smart Roku TV with soundbar. -Massage chair in master bedroom -Balcony & Dining Area w/ Ocean +Bay Views -In-unit W/D -Many conventional & USB Outlets -Arcade level features b-ball hoop, pool tables, ping-pong, shuffleboard, air-hockey -Outdoor tennis court -Large heated indoor pools -can swim full laps -Sauna and Gym -Board games in unit -Fast Wifi

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.

4.93 out of 5 average rating, 122 reviews

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.

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, 392 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!

4.97 out of 5 average rating, 198 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

Pines Getaway - Berlin Tree Light & Ice Ice 11/28

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

4.92 out of 5 average rating, 185 reviews

The exterior of the multi-story townhouse is presented along a serene waterway. Balconies are visible on the front, while a clear blue sky reflects onto the calm waters. Boat docks are positioned nearby, enhancing the waterfront atmosphere.

Townhouse in Ocean City

IslandCoveParadise:LuxNewlyBuilt-Brdwk pool/2CarGg

We welcome you, your family and friends to stay at our luxury, Newly Built, beautifully furnished, & decorated 3 BR 3.5 BA w/2 parking garage spaces plus free street parking, and an outdoor pool on 25th street. Relax and enjoy the AMAZING VIEW on the water front from our triple balconies, just 2 blocks (3-4 minutes walk) from the boardwalk & the beach. Steps from Jolly Rogers Amusement Park and many miniature golf courses. Within walking distance are restaurants/, shopping, & nightlife.

4.96 out of 5 average rating, 483 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 :)

An open kitchen-living area features modern black cabinetry and stainless steel appliances. A dining table is positioned near a large window, offering views of the ocean. Soft furnishings create a relaxed atmosphere, while natural light floods the space through the glass slider leading to the balcony.

4.92 out of 5 average rating, 299 reviews

Nice 2 BR Oceanfront, Year Round Fun & Amenities!

Gorgeous kitchen & main areas renovated March ‘22. 2 bedroom, 1.5 bath, direct oceanfront condo on 7th floor of Golden Sands building in OC. It’s clean, comfy, stylish, full of amenities & in a great location. Great WiFi, 3 TVs with cable, DVD, well stocked kitchen & stunning ocean view with large balcony. Top floor has indoor pool, fitness room, sauna & game room. Outdoor pool, tiki bar, gift shop, market & deli open weather permitting in May, then daily by Memorial Day.

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, 135 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

An open-plan kitchen and living area feature a light wooden counter with three stools. A fully equipped kitchen is visible, including a refrigerator, while a comfortable seating area with a cream-colored armchair and a coffee table is also present. Natural light enhances the inviting space.

4.88 out of 5 average rating, 162 reviews

Water Front Condo w/Pool Short Walk to Beach

FIRST FLOOR UNIT Bayside Condominium Sleeps 4 - 6 max Walking Distance to Northside Park Walk to the Ocean , don't worry about beach parking NON SMOKING 1 Bedroom 1 Bath condo, First floor unit with an outside deck This Air Conditioned, One Bedroom Condo has a fully equipped kitchen, washer/dryer, full refrigerator. There is a Queen bed and a full bed along with 1 Queen Sleep sofa in the living room *MUST BE 21 OR OVER* No Pets!

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, 248 reviews

Bayside Retreat in the Heart of Ocean City!

Newly renovated condo!! -Water view. Watch the boat traffic. -Oversized balcony with comfortable seating. -Comfy LoveSac couch. -Walk to boardwalk or beach - 15 minutes. -Walk to Jolly Roger amusement park. -Fish off community dock down below unit. -Close to dining and shopping. -Kitchenette for cooking meals. -Fast Wifi and Streaming TVs. -Fully Stocked Home. Clean linens, towels, toilet paper, paper towels & more!

A modern living area features a light-colored sofa paired with two brown leather armchairs. A round wooden coffee table graces the floor, complemented by a textured area rug. Floor-to-ceiling glass doors provide unobstructed ocean views, while floor curtains add a pop of color.

4.91 out of 5 average rating, 136 reviews

Oceanfront 2 Bedroom-Sleeps 6-Indoor/Outdoor Pool

Kick back and relax in this beautiful and modern newly remodeled condo in Golden Sands! This rare 2 bedroom, 1.5 bathroom unit has an amazing Master Suite with full-length windows providing panoramic views down the coastline, and direct access to the private patio. Renowned building amenities include outdoor pool, top floor indoor pool, gym, tiki bar, sun deck & more. Linens & towels included!

Popular amenities for Ocean Pines waterfront rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

The exterior of a three-story waterfront condominium is displayed, featuring multiple balconies and large windows. The building's design incorporates modern finishes with a dark roof and contrasting lighter siding. Surrounding greenery and a canal enhance the setting, providing a serene atmosphere.

5 out of 5 average rating, 33 reviews

Luxurious Bay/ Ocean view Splendor 4 BRS elevator

A serene ocean scene captures gentle waves lapping at a sandy shore. The horizon is lined with soft, multicolored clouds reflecting the light of a fading sun, blending shades of blue, orange, and pink across the sky.

4.89 out of 5 average rating, 18 reviews

La Pescadora - Cozy. Coastal. Completely Yours.

A view from the balcony presents the calm ocean reflecting the blue sky, with sandy beach visible in the distance. The foreground includes a parking area and the adjacent building has multiple stories with balconies overlooking the beach.

5 out of 5 average rating, 72 reviews

Ocean City Beach Retreat with Linens Included

4.86 out of 5 average rating, 146 reviews

Amazing oceanfront view 3 blocks from boardwalk

A private covered back deck features two turquoise chairs, offering a view of a tidal lagoon. The scene includes a railing highlighting the outdoor space and includes vibrant green vegetation. Soft clouds are visible against a blue sky, enhancing the serene atmosphere.

4.88 out of 5 average rating, 8 reviews

Beachy Getaway

A small wooden table is surrounded by two wicker chairs with cushioned seats, located by a large window overlooking the ocean. A vase filled with colorful flowers is centered on the table, complementing the serene coastal view.

4.94 out of 5 average rating, 18 reviews

Let the Shenanigans begin!

A tranquil bay view at dusk features a wooden pier extending over calm waters. The soft colors of the sunset reflect on the surface, while silhouettes of birds can be seen perched on the pier. Grassy areas border the water, enhancing the serene landscape.

4.96 out of 5 average rating, 136 reviews

Beautiful Bayfront Condo!

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 out of 5 average rating, 56 reviews

SuperHost! Amazing OceanFront View with 2 Pools!

Waterfront house rentals

4.97 out of 5 average rating, 29 reviews

An elevated beach house stands gracefully by the canal, with a spacious upper deck visible under a colorful twilight sky. Lush trees frame the property, while a wooden dock provides direct access to the water, creating a serene and inviting coastal atmosphere.

Home in Ocean View

Cozy Stylish Waterfront 3BR Kayaks Fireplace Porch

4.96 out of 5 average rating, 79 reviews

A cozy seating area is positioned on the waterfront, featuring plush cushions and decorative pillows. Two lanterns with candles add ambiance. Lush greenery and a clear sky are visible in the background, enhancing the serene view of the water.

Home in Berlin

Private pool, waterfront, kayaks, bikes, firepits!

4.9 out of 5 average rating, 50 reviews

The Chesapeake House

A spacious bedroom features natural wood paneling and exposed beams. A comfortable bed is dressed in a patterned blanket, while large glass doors open to a private balcony with ocean views. Soft blue curtains frame the entrance, allowing natural light to fill the room.

4.97 out of 5 average rating, 29 reviews

Seahaven

A modern kitchen showcases a spacious island with seating for four. Elegant cabinetry and stainless-steel appliances complete the design. Natural light floods the area, highlighting the marble countertop and the decorative accessories. A large TV is mounted on the wall for convenience.

5 out of 5 average rating, 50 reviews

New waterfront home on bay, quick walk to beach

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 exterior of the waterfront home features a large deck with two turquoise chairs and a small table, inviting relaxation. Expansive glass windows allow for natural light, while the unique roof design adds character to the overall structure.

5 out of 5 average rating, 3 reviews

52 lookout Point

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.

4.8 out of 5 average rating, 25 reviews

Ocean Pines 3BR 2BA Canal Front Home with Sunroom

Waterfront condo accommodation

A balcony railing frames a wide view of the ocean, where gentle waves meet a sandy shore under a clear blue sky with scattered clouds. The horizon line is visible, enhancing the sense of openness and tranquility.

4.89 out of 5 average rating, 110 reviews

One Bedroom Beachfront Apartment Mid-Town

4.88 out of 5 average rating, 128 reviews

A partial view of the ocean is visible from the balcony, showcasing the sandy beach and a section of the pool below. Beach umbrellas and chairs are arranged along the shore, set against a clear blue sky.

Condo in Bethany Beach

Featured on HGTV! Bethany Beach Ocean Front Condo

An open-concept living and dining area features a wooden dining table set for six, complemented by modern chairs. A comfortable seating arrangement with light-colored couches is situated near large windows, offering views of the surrounding area. A mounted TV and decorative elements enhance the space.

4.96 out of 5 average rating, 124 reviews

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom

4.84 out of 5 average rating, 177 reviews

Love Above the Waves-Best Ocean View & Heated Pool

A spacious balcony offers unobstructed ocean views, featuring two comfortable wooden chairs and a small circular table. The bright blue waters and clear sky create a serene backdrop, enhancing the feeling of open outdoor space.

4.98 out of 5 average rating, 101 reviews

Beautiful 2BR 2BA oceanfront condo at the Atlantis

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.

4.97 out of 5 average rating, 201 reviews

Luxury Oceanfront Escape!

An open-concept living area is featured with beach-inspired decor, a spacious sofa, and a dining table for six. Large sliding glass doors provide access to an oceanfront balcony with stunning views. A ceiling fan is installed for added comfort.

4.99 out of 5 average rating, 147 reviews

🌊Carousel Oceanfront 2 Bedroom Amazing Amenities

The oceanfront view includes soft sandy beaches leading to calm waters. Dunes with sparse grass cover offer a natural barrier, while a small wooden walkway provides access to the beach. A building with a red roof and white exterior is positioned nearby, enhancing the coastal setting.