House vacation rentals in Ocean Pines

5 out of 5 average rating, 30 reviews

A tranquil view of the waterfront shows trees reflecting on the calm water's surface. A blue boat is visible on the shore, surrounded by lush greenery and a serene, natural setting.

Home in Lewes

Bradley's Bayou

Welcome! Visit our quiet secluded neighborhood 20/25 minutes from Rt. 1 restaurants, beaches & outlets. Our waterfront home has beautiful views & reasonable prices. This is a boating & crabbing community with a community pool, tennis courts, crabbing docks & playground. Fun & easy walking and biking for families! Bring creek boots! NOTE: Linens/towels NOT provided. Bring your own! Or Rental suggestion: Sheets at the Beach, LLC 2025 Pool info: schedule in "add'l photos" No smoking/ No pets

4.78 out of 5 average rating, 23 reviews

A spacious outdoor deck overlooks a serene waterfront view, featuring several white adirondack chairs arranged for relaxation. The lush green lawn leads down to the water, where a fire pit is positioned nearby, providing a peaceful gathering spot.

Home in Ocean City

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.

Guest favorite

A welcoming dining area features a wooden table surrounded by blue chairs, creating a casual space for meals. The open floor plan is complemented by modern cabinetry and shelving in the background, while natural light enhances the bright atmosphere.

Home in Ocean Pines

5 out of 5 average rating, 46 reviews

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.

4.88 out of 5 average rating, 58 reviews

The exterior of a single-story home is shown, featuring a screened front porch with ample seating space. Lush green grass surrounds the house, framed by large trees. The entrance is marked by a set of white steps leading to a door, showcasing a welcoming appearance.

Home in Ocean Pines

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.

An open-concept living area displays light blue walls and a wooden floor. A spacious couch, paired with armchairs, surrounds a central coffee table. Large windows and a ceiling fan enhance the airy atmosphere, and a decorative rug adds color to the space.

5 out of 5 average rating, 4 reviews

Bayside Resort w/2 Master Suites, Turn Key!

This home has 6 bedrooms, 4 full bathrooms and accommodates up to Max 14 guests (up to 10 adults) There are many upgrades throughout the home including a beautiful gourmet kitchen with stainless steel appliances, a large kitchen Island with granite counter tops and unique backsplash and extra large, deep farm sink. Whether your passion is golf, exercise, the outdoors, nature, fishing, water sports, kayaks, biking, or music there is always something to do for everyone, young and old alike.

A spacious living area is highlighted by large windows that allow natural light to illuminate the soft color palette. Comfortable seating arrangements are provided with striped armchairs and a neutral sofa, complemented by a decorative area rug. A sleek fireplace adds warmth to the space.

4.95 out of 5 average rating, 19 reviews

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

5 out of 5 average rating, 4 reviews

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.

4.76 out of 5 average rating, 92 reviews

The house is situated on a landscaped lot with manicured lawns and trees, providing a serene setting. A gravel driveway leads to the front of the home, where a covered entry is visible. The surrounding trees consist of various shades of green.

Home in Frankford

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.

4.78 out of 5 average rating, 45 reviews

A charming beach cottage is nestled among trees, featuring a welcoming porch and large windows. Surrounding the home, multiple adirondack chairs are positioned over a gravel area, with a grill nearby and a hammock hanging between trees, inviting relaxation in a peaceful setting.

Home in Lewes

Bring your flip flops and relax! Adorable beach cottage in a quiet, gated community just a short drive from the hustle and bustle of downtown. Enjoy the outdoor area at home with a fire pit, grill, and games or explore the wooded trails, crabbing dock, or community pool. The pool is open on weekends only from the Saturday of Memorial Day weekend until full-time hours begin on or about the 12th of June each year. CLOSES Labor Day weekend. You must be at least 25 years of age to rent.

5 out of 5 average rating, 28 reviews

A spacious sunlit seating area features large windows with natural light pouring in, highlighting a comfortable sectional sofa with cushions. A wooden coffee table sits atop an intricate area rug. Nearby, a chair and side table contribute to the inviting space.

Home in Georgetown

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.