Waterfront holiday rentals in Ocean Pines

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.

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!!

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.

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!

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

Luxury Oceanfront Escape!

This unique place has a style of its own. Wake up, pour your cup of coffee, and watch the sunrise from your direct oceanfront balcony. The beach is a few short steps away. Walking distance to many restaurants and shops! This recently renovated one bedroom condo features an outdoor shower, an elevator, fully equipped kitchen, a library of books, 1.5 bathrooms, Wi-Fi, large screen smart tv, bedroom tv, parking spot, washer/dryer and so much more! Fresh linens, towels, and toiletries included.

Breezy Point #305 - Rooftop Deck Panoramic Sunsets

Welcome to Your Bayside Escape at Breezy Point! Step into style at this sleek bayside condo where modern comfort meets bayside views. Relax on the rooftop terrace and enjoy stunning sunset views and the fresh air. Tucked just off 28th Street, you're near restaurants, shops and quick bites. The boardwalk and beach are an easy walk or a quick drive away. A comfortable and convenient home base for couples and families. Hosting a bigger group? Ask about our other units in the same building!

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 :)

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!

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.

Nautical at 82 Newport- private dock & waterfront

Experience this spacious waterfront home featuring 6 bedrooms and 3.5 bathrooms, including 2 master suites. Enjoy a game room, hot tub, and two expansive outdoor areas perfect for sunset views. Recently updated and meticulously maintained, this home offers a clean, inviting atmosphere for your getaway. Ideal for families or groups seeking relaxation and fun by the water! A local manager is here to ensure everything goes smoothly. Driveway parking for 4 vehicles.

Coastal Retreat near the beach

Kick back and relax in this calm, stylish space just 15 minutes from Ocean City MD beaches. The unit has marsh and water views of Assawoman Bay/Manklin Creek. Located across the bay from Ocean City , MD you are close to the action but can retreat back to a quiet sanctuary when you are looking for some relaxation away from the beach crowds. If you like nature, frequent visitors include, deer, fox, blue heron, egrets, bald eagles, owls and many other birds.