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Ocean Pines House Rentals

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    Travellers to Ocean Pines are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    All 22 Rentals in Ocean Pines
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    14 Hickory Way1 / 14
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    790 Ocean Parkway1 / 17
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Balcony
    • Shared Outdoor Pool (Unheated)
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    • Terrace
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    Pet friendly
    Kid friendly
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    About this property
    Home Away From Home Enjoy this quiet, family-friendly home near the water complete with a full kitchen, furnished balcony, backyard, and outdoor fire pit, all just a short walk from a community pool, public parks, and a golf course. On warm days, head to the sandy beaches of Ocean City, just a...
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    21811, Ocean Pines, Maryland
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ravishing Riverview Come to the enchanting Maryland coast and be charmed by this fully renovated, contemporary townhome with sweeping views of St. Martin's River. With its open and airy layout, this home is ideal for entertaining family and friends. Offering plenty of cozy seating and inviting...
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    21811, Ocean Pines, Maryland
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Balcony
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    West Ocean City Bay Views Take a well-deserved break along the Atlantic Coast with the whole family or a few friends at this spacious, three-story, canalside home with a dock! Featuring three comfortable bedrooms, this rental is located just two miles from the Ocean City inlet, four miles from...
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    21842, Ocean Pines, Maryland
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dockside Retreat Your vacation experience will be truly memorable at this uniquely round home with bright and fresh decor and an electric fireplace. Enjoy the comforts of your surroundings or launch your kayaks and SUPs from the dock for a little water adventure. The outside seating offers fresh...
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    21811, Ocean Pines, Maryland
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Waterfront
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    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great Grand Port Spend your vacation in comfort at this spacious, canalfront home in Ocean Pines, complete with two decks and a private dock from where you can launch the provided kayaks. Inside, there is plenty of living space for your large family, a full kitchen for easy meal prep, and...
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    21811, Ocean Pines, Maryland
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Smoking allowed
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    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 to enjoy dining outdoors, and a porch swing on the lower patio perfect for summer evenings....
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    21811, Ocean Pines, Maryland
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Serenity on Aurora Ct. You will fall in love with this delightful home located within the Ocean Pines Community. The spacious floor plan, full kitchen, furnished deck, and outdoor fire pit will make this place your ideal family getaway. There are four TVs throughout, as well as a PlayStation 2,...
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    21811, Ocean Pines, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sandy Pines This gorgeous home is the perfect spot for families to enjoy a getaway! The home offers loads of activities including a game room with foosball, Ping-Pong, and pool tables. There is a shared swimming pool, tennis courts, and basketball courts on-site and are available for guest use. The...
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    Location Information
    21811, Ocean Pines, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Balcony
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    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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    Location Information
    21811, Ocean Pines, Maryland
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
    • Waterfront
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cottage on the Cape Peaceful relaxing days await you in this canal front home situated in a quiet neighborhood, with a furnished porch and deck perfect for gathering after a long fun day at the beach. This brightly decorated home offers spacious living, a full kitchen, private washer and dryer,...
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    Location Information
    21842, Ocean Pines, Maryland
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Patio
    • Cable/satellite TV
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    • DVD Player
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    21811, Ocean Pines, Maryland
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • DVD Player
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Terrace
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Between the Greens Come home to this three-bedroom vacation rental, part of the River Run Golf Club & Community, complete with an upgraded kitchen, a furnished deck, a balcony, and space for up to six guests. Dogs are welcome for a small nightly fee. This townhouse overlooks the first hole of...
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    Location Information
    21811, Ocean Pines, Maryland
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Shared Indoor Pool
    • Washer
    • Grill
    • Cable/satellite TV
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious waterfront home will sweep you away with 3 bedrooms, 2 baths, deeded dock, outdoor space and Ocean Pines character. The main level offers a living/dining/kitchen combo with a bonus family room, two bedrooms and full bath. Right off the family room, enjoy a screened in porch that also...
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    Location Information
    21811, Ocean Pines, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Washer
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    • Patio
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    • Wi-Fi
    • Grill
    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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    Location Information
    21811, Ocean Pines, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Shared Indoor Pool
    • Parking
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    • 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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    21811, Ocean Pines, Maryland
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    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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    21811, Ocean Pines, Maryland
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    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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    21842, Ocean Pines, Maryland
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Patio
    • Private Indoor Pool
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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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    21811, Ocean Pines, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
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    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, waterfront, picnic...
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    21811, Ocean Pines, Maryland
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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