Holiday rentals with a patio in Ocean Pines

Gorgeous New Beachfront! King Bed, Direct Sea 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!!

Ocean Pines Chalet

Nestled in the tranquil Ocean Pines, MD, Ocean Pines Chalet is a picturesque 4-bedroom, 3.5-bath haven exuding coastal charm. This delightful retreat is surrounded by a plethora of local amenities including community pools, parks, tennis and basketball courts, skate parks, golf, and a yacht club. A 15-minute drive from the bustling Ocean City beaches, it offers the perfect blend of serene living and beachside excitement, making it an ideal getaway for those seeking both relaxation and adventure

Ranch Stay- Farm Animals, Jacuzzi, Arcade, Beaches

Welcome to the Swedish Cowboy, your ultimate escape! This unique BARNDOMINIUM home is designed to offer a memorable retreat for up to four (4) guests, with the flexibility to accommodate two (2) additional guests for a small fee. Enjoy the charming backyard where you can meet a variety of fuzzy and feathered friends or head inside and play on the arcade or relax in the jacuzzi. Perfectly situated near popular beaches and bustling boardwalks, you'll have plenty of options for fun and relaxation.

Central Haven with Great Fenced Yard

You will be close to everything when you stay in this centrally-located home. The rear deck and grill are great for enjoying time outside. There's a fenced rear yard, making this home a perfect choice for man's best friend. We welcome dogs of any breed, size, and weight. We do offer size-specific pet amenities, so please share a photo of your dog when booking, or provide a basic description so we can set out appropriate amenities. For those traveling with cats, please inquire before booking.

OceanPinesFamilyBeachRetreat~JettdTub~KingBed~Golf

Immediate removal of stress at the front door. Being nestled in a marina’s serene waterfront & nature park is good for the soul. Relax in a jetted tub after a sun filled day & an al fresco meal on a back porch with charming outdoor dining. An open concept main level features large windows & comfortable seating through the entire property. 2 full bathrooms upstairs & a king sized bed provide maximum comfort & outdoor living on 2 balconies. Additional fees for pools, pets, >3 guests may apply.

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!

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines

Beautifully updated and recently renovated, rancher on a great street in Ocean Pines perfect for families and adults looking for a relaxing stay. We offer 3 bedrooms and 2 bathrooms on one level, with new large flat screen TV's, stainless appliances, and everything you'll need for your stay. We have a large driveway and a screened patio. Ocean Pines boasts over a dozen parks and walking trails, a public Yacht Club, 5 pools, 2 marinas, and a championship golf course - 10 min to the beach!

Cottage in the Pines

The mid-century modern house sleeps 6 with 3 bedrooms and 1 ½ baths. There is a peaceful back porch, parking for 3 cars, laundry, and wifi. Ocean Pines has community pools, tennis and pickleball courts, a golf course, yacht club, and playgrounds. It’s a great place for fishing, boating, kayaking, biking and hiking, and just a 10-minute drive to the boardwalk or a 20-minute drive to Assateague Island National Seashore. Guests can access Ocean Pines pools and beach club for a fee.

Sea Dunes King Suite, Exclusive Private Beach - DOG FRIENDLY!

Unwind and chill in this boho coastal inspired guest suite on the ocean side. At Sea Dunes' private guest king suite, the surf and sand are steps away. Get ready to pack your cooler and enjoy a day in the sun on this beautiful, private dog-friendly beach. Sea Dunes is located in Fenwick Island, DE and nestled between protected state nature parks. Just a short trip in the car to a marina with watersports, kayak adventures on the bay, local dining, farm markets and shopping.

RARE 4BR 3BA on Golf Course 10 min to Beach

TWO primary suites (4BR) and TWO living areas make this house double the fun! Our relaxed and well-equipped home on a beautiful golf course is just 10 minutes from Ocean City. Enjoy all the amenities of Ocean Pines (pools, tennis courts, golf course, parks and walking trails). Parking for 6+ cars. House is loaded with well equipped spacious kitchen, great room with awesome entertainment setup, and tons of extra bedding options.

3-bedroom cottage in Ocean Pines

Beautiful, comfortable 3-bedroom cottage perfect for families and adults looking for a quiet, relaxing stay. 10 minutes drive to Ocean City beaches and a short drive to the Assateague Island National Park. Ocean Pines amenities include 5 pools ($17 per-person fee), crabbing piers, basketball courts, biking, hiking, golfing, skateboard park, boating, fishing, along with restaurants, shopping, and a weekly farmers market.

Waterfront Wonder

Spacious two-story waterfront home on the St. Martin River—just minutes from Ocean City and Assateague, yet peacefully nestled in a wooded family-friendly community. Enjoy fresh linens, thoughtful amenities, and a private dock with stunning views. Not available for Senior Week. We’re flexible with most other requests—just reach out! Perfect for Oceans Calling.