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Ocean Pines Holiday Rentals

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    Travellers to Ocean Pines are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    All 16 Rentals in Ocean Pines
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    14 Hickory Way1 / 14
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    The Brooklyn Cottage Come relax in this tranquil, renovated farmhouse and leave the daily grind behind! Let the days slip away as you explore the local attractions and soak in your private hot tub. With both an interior and exterior that have been beautifully updated in a colorful, Key...
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    Ocean Pines, Maryland 21811
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Battersea on the Canal You’ll fall in love with this tranquil wooded retreat overlooking a canal with a private dock for a small boat or to launch your kayaks. You can relax on the deck with a picnic table, a gas and charcoal grill to enjoy dining outdoors, and a porch swing on the lower patio...
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    Ocean Pines, Maryland 21811
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Balcony
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    Kid friendly
    Smoking allowed
    About this property
    Bayview Beauty Soak in gorgeous views of the Ocean Pines Yacht Club and Marina from the outdoor deck and three-season sunroom of this spacious bayfront townhome! You'll enjoy an open and inviting living space with a cozy gas fireplace, colorful beachy decor that will set the mood for fun days in...
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    Ocean Pines, Maryland 21811
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
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    About this property
    Paradise in The Pines Spend your vacation in sunshine and comfort at this canalfront home in Ocean Pines, where you'll have 60 feet of waterfront and a private dock that can accommodate a 30-foot boat! Enjoy a pair of bikes to take around the neighborhood, as well as a private deck with a gas...
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    Ocean Pines, Maryland 21811
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Owners will meet you at the door and set you up for a successful getaway. Plenty of open spaces for a family to enjoy in a simple rancher that is near the beach and bay. Two sunrooms, bbq grill, picnic table, outdoor seating and quiet backyard away from street. Parking for 4 cars off the road....
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    Ocean Pines, Maryland 21811
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful coastal cottage with spectacular water view, newly remodeled kitchen, solid maple floors, beach décor, 3 bedrooms 2 bath sleeps up to 8. 3 bedroom, 2 Bath with private waterfront views close to the beach. Enjoy your vacation on a quite cul-de-sac in in well maintained neighborhood, bike...
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    Ocean Pines, Maryland 21811
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful home is just a short distance to the North Gate of Ocean Pines, and minutes from Ocean City. This 4 bedroom 3 1/2 bath home features full kitchen, washer, dryer, dishwasher, Microwave, 5 TVs, ping pong table, and a screened in porch. The home is large enough to accommodate a large...
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    Ocean Pines, Maryland 21811
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Shared Indoor Pool
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful four-bedroom home with an open floor plan and vaulted ceilings. This relaxing and comfortable home sleeps 10 with plenty of room to spare. Upscale amenities and a private wooded lot with a 2 room outdoor shower, pond, hot tub, New extended vinyl deck, herb garden, hammock, and florida...
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    Ocean Pines, Maryland 21811
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Grill
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make this charming four bedroom, two bath home your retreat in Ocean Pines, just minutes away from the hustle and bustle of Ocean City. Easily accessible from the South Gate, this home has just been updated with new living room and dining furniture, as well as five flat screen televisions for lazy...
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    Ocean Pines, Maryland 21811
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    To secure a do-as-you-please getaway in Berlin, Maryland, be sure to book this charming 2-bedroom, 1-bathroom vacation rental house with flexible accommodations for up to 6! Affiliated with Ocean Pines Resort, this home allows access to the on-site golf course, 5 pools, tennis courts, and marina...
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    Ocean Pines, Maryland 21811
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Patio
    • Private Indoor Pool
    • Washer
    • Wi-Fi
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Go on a beach retreat to Ocean Pines and stay at this 3-bedroom, 2-bathroom vacation rental home. This LGBTQ-friendly home boasts 1,486 square feet of tasteful living space, a deck with a screened-in area, a gas grill and access to community amenities like 3 outdoor pools, an indoor pool and...
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    Ocean Pines, Maryland 21811
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    • Wi-Fi
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled within walking distance of the bay and 3 miles from the famous Ocean City attractions, this 3-bedroom, 1-bath vacation rental is the perfect family destination. While just a short drive from the caramel corn vendors, ice cream shops, and mini golf courses along the boardwalk, this quiet...
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    Ocean Pines, Maryland 21842
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape everyday stress with a trip to White Horse Park, a bayfront community that features ample family-friendly fun! This recently renovated vacation rental boasts 2 bedrooms, 1 bath, a well-equipped kitchen, and a private outdoor dining area, with access to a community pool, marina, picnic...
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    Ocean Pines, Maryland 21811
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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