Holiday rentals with a patio in Ocean Pines

Bayfront Paradise with Pool - 32nd St

Welcome to your personal Bayfront Paradise. Enjoy amazing sunsets on your personal bayfront deck with a cozy fire pit. At Bayfront Paradise you are a couple minute walk to jet ski rentals and Jolly Rogers Amusement Park. The walk to the beach is a short 10 minute walk. You can also enjoy a day of fishing, crabbing or boating from your private dock. This home is perfect for a couples retreat or a getaway with the family. The property is thoughtfully stocked to provide you with the perfect stay!

Downtown OC Townhome! - (B)

Experience the ultimate seaside escape in our spacious 3-bedroom beach house, designed with families in mind. Just 100 steps from the sand and boardwalk, you’ll have the beach at your doorstep. Stroll to nearby dining gems like Spain Wine Bar, The Lazy Lizard, & MR Duck. Enjoy a perfect blend of relaxation and convenience in a beautifully appointed home that promises cherished memories by the ocean. This is one of 2 units that mirror each other. They can be booked together for larger groups!

19th Century Coastal Cottage with Modern Amenities

Built from “clinker bricks” in 1941 to house poultry feed, this Airbnb is a dreamy place to slow down. Exposed wood beams and interior brick walls as well as all the luxuries required for a rural escape. This charming cottage near the beach & is surrounded by enchanted gardens. You will swoon over the carved marble bathtub and gorgeous living areas. Perfect for a romantic getaway, Hobbs and Rose Cottage is waiting to create a memorable experience for you! NEW for 2025, our mediation room!

El Ancla

stunning bay sunsets and idyllic outdoor space at this peaceful waterfront home in prime 94th street location with amazing breeze. Recently rehabbed - new hardwood floors, bathroom, and brand new interior and exterior furniture. Bayfront deck with your own boat slip. Brand new casual comfort deck furniture. Remote work with a view! 10 min walk to beach, playground, community arts center, mini golf, bars. Beach chairs included. We can provide pack n play upon request

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!

Luxurious & Location 94th st

This stunning bay view townhouse is the perfect blend of luxury,comfort and relaxation.Step outside to the porch,a perfect spot for outdoor dining,mornings coffee,relaxation or simply enjoying a quiet evening under the stars.This prime location offers within 200-300 ft both a tennis court,basketball court and grocery store.Embrace the coastal lifestyle and experience. This townhouse features two spacious living rooms ideal for cozy family gatherings.

Villa Caribbean OCMD

Take it easy at this unique and tranquil getaway showcasing a 180-degree view of the St. Martin River Perfect neighborhood for walking, riding bikes, golf course within ocean pines 13-minute drive from Ocean City Beaches. Comes with one Ocean Pines Beach Club parking pass located on 49th street, where there is a restaurant, bar, restrooms, and pool. The pontoon boat is not included with the rental, but the boat slip is available upon request.

Charming Northside Park Condo w Pool, Walk 2 Beach

This charming 1 bedroom, 1 bathroom condo w/ a Pool is only a block and a half from the beach. You'll love relaxing on the deck that overlooks scenic Northside Park and the bay. An ideal getaway for couples or a small family. This unit has an Eat-in kitchen, washer & dryer, 2 TVs, Central Air, and high speed WiFi. This third floor two-story condo is in the Raffles Condominium complex, located on 127th Street in OCMD.

Summerset Coastal Cottage

A coastal retreat welcomes YOU! Family-oriented community. ☀️ 5 miles from Bethany Beach. 4 bedroom, 3.5 bath. 1 of the bedrooms is separate bonus room over the garage with private bath. Comfortable living space, fully- equipped kitchen w/ double wall oven & cozy fenced-in patio area. Community gym, 3 Pools, Pickle ball, walking trails, and playground. Beach shuttle just steps from the front door runs 5 days/week.