Waterfront holiday rentals in Ocean Pines

4.95 out of 5 average rating, 255 reviews

Home in Montego Bay

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!

Guest suite in Ocean Pines

4.95 out of 5 average rating, 377 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!

4.96 out of 5 average rating, 169 reviews

Condo in Ocean Pines

Getaway in Ocean Pines

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

4.98 out of 5 average rating, 170 reviews

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.

4.96 out of 5 average rating, 449 reviews

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 :)

4.91 out of 5 average rating, 174 reviews

Home in Ocean Pines

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!

4.96 out of 5 average rating, 275 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.

4.92 out of 5 average rating, 281 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.

4.96 out of 5 average rating, 253 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.

Guest suite in Ocean City

4.98 out of 5 average rating, 367 reviews

The Elbridge Bayfront Studio

The Elbridge is a luxury studio apartment in downtown Ocean City. Beautiful bay view from studio windows. 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, the boardwalk, and the beach!

4.99 out of 5 average rating, 124 reviews

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