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, 262 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!

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.

4.97 out of 5 average rating, 109 reviews

Gorgeous New Beachfront! King Bed, Direct Sea 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!!

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, 121 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, 391 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, 196 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.

Apartment 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

4.96 out of 5 average rating, 482 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 :)

A modern kitchen is complemented by a spacious dining area and cozy living room with ocean views. White cabinetry and stainless steel appliances enhance the kitchen, while large windows allow natural light to fill the space, highlighting the wood-paneled ceiling.

4.96 out of 5 average rating, 161 reviews

Oceanfront 1 Bedroom, Balcony, Sitting Room, Pool

Opal Osprey: This OVERSIZE one-bedroom condo has been completely remodeled... giant oceanfront balcony PLUS a large patio room on the bayside! Expansive ocean views from every angle, super easy beach access, wonderful atmosphere in the quiet north end of OC. Linens included! Property Amenities - King size bed & queen sleeper - Large outdoor pool - Elevators - Dedicated high-speed WiFi and router w/ ethernet (Xfinity 100Mbps) - 2 Smart TVS with Xfinity, Roku - Keyless check-in 24/7

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.

4.98 out of 5 average rating, 123 reviews

The Hideaway By The Bay OCMD

Relax and enjoy your stay in this bright and welcoming waterfront, 1 bed, 1 bath condo. Bring your kayaks or paddle boards! This condo is located right off of 28th street, on the bay. It is a 14 minute walk to the beach and the Ocean City boardwalk, and within walking distance to many Ocean City attractions. All guests are provided with an electronic WELCOME BOOK prior to arrival which includes everything we think they will need to know about the condo and the surrounding area.

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.

4.95 out of 5 average rating, 300 reviews

Direct Oceanfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

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, 280 reviews

Caramar Couples Retreat

This cute little first floor efficiency condo is ocean front for a perfect vacation to the beach. It’s an older building but has been partially renovated and updated. You can get to the beach by a very short walk through a private walkway from the condo building. The view from the private balcony is perfect and relaxing. WiFi provided upon check in- xfinity, Netflix, and internet. Indoor and outdoor dining areas and a full kitchen. Closet and dresser for storage use.

4.9 out of 5 average rating, 261 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.

4.99 out of 5 average rating, 134 reviews

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.

Home in Ocean Pines

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 waterfront rentals in Ocean Pines

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

A spacious balcony offers a relaxing view of the sandy beach and ocean. Colorful Adirondack chairs in vibrant hues are positioned for comfort alongside a round table, creating an inviting outdoor space. The horizon meets the gently rolling waves under a partly cloudy sky.

5 out of 5 average rating, 12 reviews

Oceanfront and on the Boardwalk!

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.

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 out of 5 average rating, 3 reviews

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

4.85 out of 5 average rating, 144 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

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, 98 reviews

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

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

4.9 out of 5 average rating, 50 reviews

The Chesapeake House

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!

The living room features two plush sofas and two accent chairs, arranged around a circular coffee table. A flat-screen TV is mounted above a gas fireplace, and large windows allow natural light to fill the space, showcasing views of the bay.

4.95 out of 5 average rating, 21 reviews

Beach Paradise 2101-Downtown Luxury Condo Bay View

4.93 out of 5 average rating, 42 reviews

A spacious three-story coastal home is highlighted by multiple wraparound decks, providing scenic views of the water. Soft evening lighting enhances the inviting atmosphere. Lush greenery surrounds the property, while a private access path leads to the beach nearby.

Home in Bethany Beach

Bethany Beach Home w/ Beach Access + HOT TUB!

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

The expansive view showcases the sandy beach stretching along the Atlantic Ocean, gently reflecting the clouds above. Features include a shared pool bordered by lounge chairs and landscaped areas. The setting sun casts warm hues over the water, enhancing the serene coastal atmosphere.

4.79 out of 5 average rating, 14 reviews

Oceanfront | Beachfront | Elevator | eFireplace

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, 45 reviews

The Oliver House

4.81 out of 5 average rating, 113 reviews

A serene view of Sinepuxent Bay stretches across the horizon, showcasing expansive grasslands and soft green vegetation. The sky transitions to warm hues of sunset, creating a calming atmosphere. A glimpse of the fishing pier is visible in the distance, enhancing the waterfront scenery.

Home in Berlin

Mosaic Life Escapes -Bayfront Million Dollar Views

Waterfront apartment rentals

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, 109 reviews

One Bedroom Beachfront Apartment Mid-Town

A comfortable living area features a gray sofa with blue accent pillows and a textured rug. Large sliding glass doors offer a view of the ocean and access to a private balcony with outdoor seating. Natural light fills the space, creating a welcoming atmosphere.

4.98 out of 5 average rating, 242 reviews

Cozy oceanfront condo with stunning ocean views

A balcony features outdoor furniture, including a couch and coffee table, offering a direct view of the beach and ocean. The sandy shore stretches out, while the waves gently roll onto the beachfront. Harsh shadows are minimized by the clear, bright sky.

4.96 out of 5 average rating, 71 reviews

Direct Oceanfront Boardwalk - Steps To The Beach

4.84 out of 5 average rating, 177 reviews

Love Above the Waves-Best Ocean View & Heated Pool

An expansive view of the beach is captured, showcasing soft sand leading to calm ocean waves reflecting sunlight under a clear sky. The horizon stretches far into the distance, with a few distant figures visible on the beach, and a neighboring building is seen to the right.

4.99 out of 5 average rating, 80 reviews

Beautiful Ocean Front Condo 2b/2ba with pool

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, 120 reviews

Ocean front condo with Balcony

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, 145 reviews

🌊Carousel Oceanfront 2 Bedroom Amazing Amenities

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.