Holiday rentals with a pool in Ocean Pines

Cottage on the water

We are located right off of Route 90 and minutes to the beach. Ocean Pines is filled with amenities. We have a public access yacht club and golf course are close to the town of Berlin for dining and a visit to the famous Burley Oak Brewery. The family will enjoy Ocean City for fun at Jolly Rogers or the Boardwalk for the rides. West Ocean city has the famous Orange Crush at the Harborside restaurant and don't forget Assateague Island and the horses. We are also 2 miles from the local winery.

Camelot

HIGHEST RATED HOUSE IN OCEAN PINES! CHECK OUT OUR AMAZING GUEST REVIEWS :) Jumpstart your ultimate beach getaway at this impressive 3-bedroom, 2-bathroom retreat house! Complete with amenity-packed living spaces with vaulted ceilings and a serene location, you’ll never hunger for entertainment at this family friendly home. Grill out on the patio, roast marshmallows by the fire pit, tee off at a nearby golf course, or enjoy some retail therapy at Outlets Ocean City! A short drive 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, >3 guests may apply.

Riverside Retreat- 3 Story/Direct Waterfront

Welcome to your ideal vacation home! This spacious three-story residence features 4 bedrooms and 2.5 bathrooms, including a king bedroom with an en-suite bath & balcony. Enjoy an open kitchen, dining area, and a stunning living room with river views. The backyard offers a private "beach" with Adirondack chairs and a picnic table. Just 20 minutes from Ocean City’s shopping, dining, and beaches. Perfect for family fun and relaxation! A local manager is here to ensure everything goes smoothly

Newly built bright and airy guest suite!!!!

Welcome to our new 2nd floor private suite with parking, patio/firepit, and self check-in private entry. We are located just minutes from the Ocean City beaches, quaint small town of Berlin, Ocean Downs Casino, Assateague, Windmill Creek Winery, restaurants, and outlets. Enjoy neighborhood amenities such as a breathtaking waterfront Yacht Club with restaurant and live music (seasonal), Robert Trent Jones Sr. golf, farm market, playgrounds, 5 pools/fee (4 seasonal), and racquet club.

Stay Salty OC Beach House

Welcome to your ultimate getaway near Assateague State Park & Ocean City! Our spacious retreat sleeps 14 guests and boasts resort-style amenities including pools, a gym, kayaks, and tennis courts. Located just moments from beaches, charming towns, and exciting attractions, you'll have everything you need for an unforgettable vacation. With a fully stocked kitchen, game rooms, cozy reading nooks, puzzles, and a balcony, there's something for everyone. Book now and let the relaxation begin!

Peaceful Beach Cottage - Sanitized & WiFi!

Fully renovated clean, sanitized, quaint house in a quiet neighborhood minutes from the beach/ocean! Community offers many amenities such as pools, restaurants, playgrounds, etc. Have peace and quiet while only being minutes from the beach and main OC drag. Very close to the casino! Voted "#1 Safest Neighborhood in Maryland!" *June-August we only accept 7 day rentals with a Saturday check in* *Memorial & Labor Day weekends have 3 night minimum with Fri check in*

Tortuga Cottage: Your All- Season Getaway

This is an escape to reacquaint with family, nature, and your best self. Come home from the beach just a few miles away to enjoy the gas fire place, outdoor fire pit, and hot tub on chilly nights, fenced in back yard. Take advantage of the parks indoor outdoor pools golf yacht club, just moments from the cottage. Dogs are part of our family, and we are happy to consider canine guests on a case by case basis. Please see policies for breeds.

Private, pet-friendly, w/game room & new kitchen

Nestled at the end of a quiet cul-de-sac in family-friendly, amenity-filled Ocean Pines, this recently updated one-level home boasts nearly 1700SF, with 3 bedrooms, 2 full baths, 2 living spaces, an open concept kitchen/living area with gas fireplace, a dining room that comfortably seats 8, a three-season sunporch, laundry room, plenty of parking and a private backyard with fire pits as well as a gas grill and eating area.