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!!

Whimsical Willow w/ Beach Club Pass and No Pet Fee

Discover this charming 3-bedroom home! With wood floors throughout, it features a king master suite, a queen bedroom, and a kids’ room with a twin-over-full bunk. Enjoy a fully stocked kitchen, fast WiFi, a screened-in porch, and a jetted tub for ultimate relaxation. Perfect for families or dual-family stays! Explore Ocean Pines or take a quick 10-minute drive to Ocean City for endless fun. Included is the Beach Club Parking Pass! Plus- A local manager is here to ensure everything goes smoothly.

Ocean Pines-OCMD Bliss at the Beach- Sat. to Sat.

Welcome to Bliss at the Beach, our charming 3br, 2ba home nestled in the desirable, beloved Ocean Pines community. Loved for its safe, quaint, family friendly neighborhoods. Find yourself less than 15 minutes away from the beautiful beaches and vibrant shopping, dining and boardwalk district of Ocean City. Enjoy the ease of the prepaid parking at the Ocean Pines Beach club on 49th street, just unload the family and walk on the beach!! Summer months Bliss is a 7-night minimum to guests 25+older

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

OC Gateway: Modern 4BR/2.5BA home (dog friendly)

Have fun with the whole family at our stylish Ocean City-convenient home! This wooded beach house boasts many modern upgrades including a beautiful kitchen with gas range, large flat panel televisions in almost every room, a washer and dryer, and even a Wii video game system in the living room! Queens in 3 bedrooms and a bunk bed with trundle in the 4th! Finally, enjoy all the amenities of Ocean Pines including access to 5 pools, a private OC beach club (w/pool!), and much more! Lic. No. 4586

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.

Waterfront Home-Turnville Creek

Nestled on turnville Creek, this 4 bedroom, 2.5 bath, pet-friendly waterfront home is the perfect place for multiple families to vacation in Ocean City. Waterfront views, spacious yard, and 10 minutes from ocean city situated behind the ocean downs casino on turnville creek. Bring your boat or a rent a boat and dock it here - there is a boat ramp a half mile down the road in our neighborhood. We hope to accommodate you and provide an experience that is becoming increasingly unique to find.

Cozy beach home away from home!

Welcome! Come enjoy a cozy experience at this centrally located home in the desired Ocean Pines Community! This home is near the playground and allows access to the on-site golf course, five pools (including indoor pool!) tennis courts, and marina for a small fee. Fun in the sun awaits 15 minutes away in downtown Ocean City, where you can stroll the boardwalk, lounge on the sand, or hit the amusement park. Plenty of restaurants, grocery stores and shopping within 15 minutes.

Hobbs & Rose | A Peaceful Cottage Escape

Built in 1941 from historic “clinker bricks,” this restored cottage is a dreamy place to slow down and reconnect. Surrounded by enchanted gardens and close to the beach, Hobbs & Rose is filled with charm—gorgeous living spaces, a carved marble soaking tub, and thoughtful details throughout. Enjoy a romantic getaway and unwind in our Sanctuary meditation room, where birdsong and forest friends welcome you. You relax—we’ve created every detail to help you feel restored.

Family Oasis - 4BR 3BA on Golf Course

TWO primary suites (4BR) and TWO living areas make this house double the fun! Our relaxed and beautiful 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.

The Beach Nut- w/ Beach Club Pass and No Pet Fee

Forget your worries in this newly updated home. The spacious open floor plan, creates the perfect place to unwind, with brand new flooring and furniture added in 2025. Just minutes from parks, boat launches, farmers markets, and pools—including the Yacht Club and Swim & Racquet Club. Enjoy easy access to Assateague Island, Ocean City Beach, and local restaurants. A local manager is here to ensure everything goes smoothly.

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.