House holiday rentals in Ocean Pines

The Oliver House

This property boasts breathtaking views of the Ocean City skyline and is nestled in a quiet neighborhood in West Ocean City. Bring your boat, paddle boards, kayaks and firewood for the most incredible vacation. Crabs and clams are plentiful and the kids can enjoy playing in the small beach area while splashing or swimming in the bay. Although you may never want to leave, it's a short drive to Ocean City's beaches and boardwalk, Assateague Island and the quaint must-see town of Berlin, Maryland.

hi-A-tus A-frame

Charming A-frame nestled in the heart of Ocean Pines. Open floor plan, softest sheets, flat screen TVs, high speed WiFi, in an amenity filled community surrounded by multiple beaches. 10 min from Ocean City and 15 min from Assateague! Sleeps 4 comfortably. Perfect for 4 adults or family. Must be 25 yrs old. Enjoy all that Ocean Pines has to offer including 5 pools, multiple playgrounds, yacht club and farmers market. Weekly rental during the high season. Please inquire about longer stays.

Sunny Days

Casual, spacious open floorplan, all on one floor with a huge back sun porch, nice front sun porch and deck. Centrally located, beaches, historic Berlin, and amenity filled community [pools, golf, pickle-ball etc.] Sleeps 8-9; king, queen, full-twin bunk, single. Must be 25 yrs old or prior service military or first responders. Recent price hikes forced us to cut the cable, switch to streaming services, and install TVs in each room. Linens and beach club parking pass available for a fee.

The Villa at Bayside Resort

Introducing a stunning, professionally decorated vacation rental property nestled in the heart of the prestigious Bayside Resort. Property Features: 4 beautifully-appointed bedrooms, 3.5 baths A spacious loft A sun-soaked living area Sun room, An elegant dining room, perfect for memorable family meals A scenic patio off of a wooded lot, offering a serene outdoor retreat. Bayside Amenities: Golf course 4 pools Fitness center Tennis courts Playground Kayaking Trails Concert Venue

Luxury home by the bay

Your perfect vacation starts here. The luxury house is located at a quiet, family friendly community. Equipped with 5 bedrooms and 3 full bathrooms, the house features new furnishings and decor throughout.  The amenity-rich community offers a large pool with kids zone, fitness center, library, outdoor fireplace, private and beautiful beach on the Assawoman Bay. You may crab at the community marina or bring your kayak or canoe and launch them right into the bay from the clubhouse pier. 

Beaches Near By

Spacious and welcoming; centrally located. Landscaped, relaxing country-like setting, clean, comfy and casual-chic decor and family friendly. Daily rental house 6 miles from Bethany Beach. NJ and MD beaches near by. Multi-night discount (3 bdrms/2 baths @ 2,000sq ft); Sleeps 9 (3 doubles/3 singles). Eat-in kitchen, central air, and washer/dryer. Smoke-free interior; no pets. Covered entries; front porch, deck and spacious yard with shade trees; Lots of parking for boats and trailers.

Holly Hill: Quiet Wooded Retreat Close to Beaches

Welcome to your ideal forest retreat! Nestled in a serene privately owned forest, Holly Hill House offers the perfect blend of being close to the busy coastal area, meanwhile allowing you a tranquil seclusion. Let your children or dogs out to explore our peaceful fenced-in front yard. The screened-in front porch is perfect for outdoor dining or simply lounging with a good book. Delaware beaches are about 30 minutes away, depending on which beach you choose and the local traffic.

Stunning Sunrise & Water View 1 mile from Beach

Look no further for your vacation rental at the beach, this house has it all! This extraordinary coastal home has amazing views of the Little Assawoman Bay and is steps away from waterfront dining locations like Harpoon Hanna's, Papa Grande's and Catch 54. Enjoy the beach in Fenwick Island, DE/Ocean City, MD which is just less than 1 mile away. This owner operated property is the beach vacation spot for you! No pets & No smoking please Owner is a licensed real estate agent

Beachy Sunset Island Townhouse!

Located in the heart of Sunset Island, this 4 bed/4.5 bath townhouse is steps away from the clubhouse and bay. Beautifully decorated and suitable for families, this home even includes baby gear and a crib so you don't have to bring anything with you. Relax on Sunset Island's private beaches and never leave the community. Everything is available at your fingertips for an unforgettable stay. With 2,400 square feet of living space, there is room for everyone!