Holiday rentals with a patio in Ocean Pines

Whimsical Willow l 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.

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.

Be our guest

Beautifully renovated guest suite in the sought-after community of Ocean Pines, just minutes from Ocean City and Assateague Island beaches and unmatchable community amenities. Enjoy a quiet place to stay in, cooking inside or out on the patio. Explore the beautiful community trails, restaurants, pools, parks, and everything that the Eastern Shore has to offer. The suite is attached to the main house with a separate entrance and is completely private. No smoking, please. No pets allowed.

Watertown 104 with OCP Beach Pass

Watertown 104 is an immaculately maintained rancher with numerous updates and plenty of space for you and your family to spread out while on vacation. Located in the amenity rich Ocean Pines, just 6 miles from Ocean City, you have the choice to go crabbing, fishing, boating, visiting the local pools, playgrounds, private and public beaches, all within a few miles. Ocean pines beach parking pass included with stay. We hope you choose to stay with us for your next trip down to the beach!

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 may apply.

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.

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.

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.

Oceanside Condo Steps From Beach

Escape to our stylish, surf-inspired ocean view condo, just steps from the beach! This bright, airy retreat comfortably sleeps 4 and features a private balcony to watch the sunrise, a fully equipped kitchen, and a luxury king bed. Perfect for a relaxing beach getaway, you'll enjoy modern amenities and direct beach access via a sandy path. Your unforgettable coastal escape awaits!

Ocean Pines Retreat with Beach Club

Escape to our peaceful Ocean Pines retreat! This updated, single-level rancher comfortably sleeps 6 and is perfect for families. Enjoy a quiet street just minutes from Ocean City. Features a modern kitchen, cozy fireplace, and exclusive access to the Ocean Pines Beach Club with a private pool, restaurant, and ocean access. Your serene beach getaway awaits!

Cozy Coastal Home in Ocean Pines

Our home is 2 bedrooms, 2 full bathrooms, detached house, with a rear deck and patio with dining table located in Ocean Pines. It's updated & modern, clean, and ready for your next beach vacation! The house has a fenced in yard and is in a very quiet neighborhood and will make a great family vacation home. We cater to families, couples and small groups.

Waterfront 3BR | Private Dock + Views

Waterfront retreat in Ocean Pines with private dock, expansive deck, fire pit & Ocean Pines Beach Club parking pass—just minutes to Ocean City and Assateague Island. Perfect for families, boaters, and peaceful getaways with sunset views right from your backyard. Senior Week unavailable. Please reach out with questions about other stays.