Waterfront vacation rentals in Ocean Pines

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Top-rated waterfront rentals in Ocean Pines

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Guest favorite

Home in Ocean City

4.94 out of 5 average rating, 221 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!

Jan 7 – 14

ﺩ.ﺇ368 per night

Guest favorite

Condo in Berlin

4.98 out of 5 average rating, 103 reviews

Amazing Waterfront in Berlin, MD- Sea Breeze Suite

1 of 5 waterfront units (Drift Inn, Sea Breeze, Coconut Grove, Coral Tides, Day Break) located at The Inn on Turville Creek in West Ocean City. Perfect for outdoor lovers or a quiet escape. Bring your paddleboards, kayaks, or just enjoy the beautiful views from the comfort of your own patio. The Inn is located approximately 5 miles from downtown Ocean City and the town of Berlin, MD (voted America's Coolest Small Town) and ~10 miles from Assateague. Stunning sunsets right from your front patio!

Sep 16 – 23

ﺩ.ﺇ695 per night

Guest favorite

Guest suite in Ocean Pines

4.95 out of 5 average rating, 354 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!

Jan 19 – 26

ﺩ.ﺇ588 per night

Guest favorite

Condo in Ocean Pines

4.96 out of 5 average rating, 109 reviews

Waterview Retreat

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

Nov 10 – 17

ﺩ.ﺇ509 per night

Superhost

Condo in Ocean City

4.85 out of 5 average rating, 103 reviews

2 Bdrm Oceanfront-Pool, Xbox, Pickleball, Gym, HBO

Stunning newly renovated 2 bedroom oceanfront condo in the premiere Golden Sands! Blue Wave is known for its unique 3-tiered wave wall and incredible ocean views from the living room and primary bedroom. SmartTV w/Xbox! Wake up to the sun rising over the ocean right out your bedroom window, and after a cup of coffee on the balcony (included!) head to the building's sun deck,fitness center, lounge, arcades, tennis court, pickleball court,beach volleyball,or indoor/outdoor pools and tiki bar.

Oct 25 – Nov 1

ﺩ.ﺇ549 per night

Guest favorite

Townhouse in Ocean City

4.97 out of 5 average rating, 352 reviews

Edgewater Escape - Bayfront Condo w/Private Porch

Welcome to our "Edgewater Escape." These buildings were built in the 1960's and literally hang entirely over the bay in downtown in 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 king sized bed and the downstairs couch pulls out into a comfortable queen bed. Full size kitchen with microwave, fridge, electric range, and coffee maker. Located on 7th street, over the bay :)

Jul 28 – Aug 4

ﺩ.ﺇ2,232 per night

Guest favorite

Townhouse in Ocean City

4.91 out of 5 average rating, 223 reviews

SunburstParadise: OceanView Boardwalk Luxury w/2🚘G

Relax and enjoy our newly updated, beautifully decorated 3 Br/ 3 Ba luxury ocean block Townhouse, (2014) which has a 2 car garage on 16th street. The end unit luxury townhouse is less than a 2 minutes walk from the beach and the boardwalk in a prime Downtown location. Enjoy beautiful sunrises Ocean View from two private balconies and drink coffee from Starbucks Coffee across street. Within walking distance are great restaurants/bars, mini-golf, shopping, amusements, and nightlife.

Jan 10 – 17

ﺩ.ﺇ381 per night

Guest favorite

Home in Ocean Pines

4.9 out of 5 average rating, 134 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!

Dec 17 – 24

ﺩ.ﺇ1,471 per night

Guest favorite

Condo in Ocean City

4.84 out of 5 average rating, 161 reviews

Beachfront 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 a breathtaking view of the beach and ocean.

Nov 21 – 28

ﺩ.ﺇ471 per night

Superhost

Condo in Ocean City

4.88 out of 5 average rating, 106 reviews

Unit 11 on 41 St Ocean Side 50 steps to beach

Dominica Beach is a 2-story condo, close to the ocean on 41st Street Only 50 paces to the sand dunes and you'll have your toes in the sand! There are no streets to cross to get the beach. Complementary linen service based on the number of guests. Within walking distance of the Convention Center, restaurants, amusement parks, mini-golf, & more. You’ll love our place because of the ambiance. It is good for couples, solo adventurers, and families (with kids).

Sep 19 – 26

ﺩ.ﺇ284 per night

Guest favorite

Condo in Ocean City

4.88 out of 5 average rating, 168 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!

Dec 21 – 28

ﺩ.ﺇ425 per night

Guest favorite

Guest suite in Ocean City

4.98 out of 5 average rating, 272 reviews

Spacious Luxury Studio in Ocean City

The Elbridge is a luxury studio apartment in downtown Ocean City. This bayside studio includes parking, a private garden entrance, and luxurious king bed. Located 4 blocks from the beach, the space is in a downtown residential neighborhood. Additionally included are bikes, bodyboards, beach chairs and a beach umbrella. Walking distance to delicious local restaurants and the boardwalk, The Elbridge is truly special.

Oct 9 – 16

ﺩ.ﺇ690 per night