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Vacation Rentals in Ocean Pines, Maryland

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about Ocean Pines

Ocean Pines, Maryland Vacation Rentals and Tourism

More than 7,000 vacationers flood Ocean Pines, Maryland every summer. The resort community is only a 15 minute drive from the action of Ocean City, but Ocean Pines vacation rentals offer guests peace and privacy.

Ocean Pines boasts five swimming pools, an 18-hole golf course, two marinas, basketball and tennis courts, lakes, playgrounds, and much more. Your Ocean Pines rental will be conveniently located next to everything you’d ever need or want to do on your vacation!

Why Ocean Pines rentals? 

Rentals in Ocean Pines are great to escape to in the summer; and you really can escape to them! While the Atlantic Coast is no stranger to tourism, Ocean Pines is a secluded haven for vacationers who don’t want to fight for a spot to sunbathe on a crowded beach, but still hope to enjoy the water.

If an intimate weekend getaway, or month-long diversion, is what you’re looking for, then an Ocean Pines rental (or two) has your name on it! Rentals in Ocean Pines range from villas to condos to townhomes, so you have some thinking to do before you find the right accommodation. But unlike with a hotel, with Ocean Pines rentals, you can really customize your vacation.

To get started, browse the quaint Ocean Pines vacation rentals on display here. 

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Check out more areas which feature homes, villas, cabins, cottages, or condos.

Ocean Pines things to do

 

Thrasher's French Fries

I figured I'd wait until I was safely back in DC before writing a review that disagreed with the masses... I was hungry, I saw a long line of people, and I...read more

 

Malibu's Surf Shop

100% Authentic. If you want to experience what a Surf Shop was like before rampant commercialization, Treat yourself, and Stop by Malibu's. If you are in...read more

 

Ocean City Beach

parking on the street is great (if you can find it) but there is a huge parking area at the beginning of the boardwalk ($3 an hr) the bathroom is right...read more

 

SuperFun Eco Tours

The philosophy of ecotourism is simple. Observe, learn, and leave a minimal footprint. So when we killed dozens of fish with a trawling net during this...read more

 

Assateague Island National Seashore

This is ocean city without the crowds, cars and villas. The beach was endless with lifeguards designated to a certain section if you have children or feel...read more

 

48th Street Water Sports

Absolutely love this place. If you need a kayak, paddle board, or hobie this is the place to be. Mike, Mike, and Richard are great instructors and very...read more

 

Ocean Gallery

This gallery is so full of amazing artwork that you really cannot see any of the walls in the place! From the outside, it doesn't look like much. Inside,...read more

 

Coastal Kayak

Perfect location for kayaking or stand-up paddling. We've done both here. Beautiful setting, friendly service, ample parking, reasonable prices, quality...read more

 

The Globe

I absolutely love this adorable restaurant in the heart of America's Coolest Small Town. This place is just too adorable - fresh made chips and delicious...read more

 

Trimper's Rides

Afternoon wristband special is a great deal....Trimpers is everything that a boardwalk amusement ride park should be. Lots of variety and fair pricing.read more

 

Old Pro Golf

We tried to golf the indoor course at 11AM on a rainy day but left because there was a 45 min wait to start the course. We came back to give it another try...read more

 

Chauncey's Surf Shop

I was a K-Coast kid growing up in town, but one stop in Chauncey's 5 years ago has completely changed my loyalty. Blair, Chauncey and the crew are...read more

 

Old Pro Golf

Although we were told our party of 6 hard to split in to two parties of 3 we still were able to play together. We chose to do the indoor course just because...read more

 

Cupcakes In Bloom

Not sure if we were there on a bad day or not but we bought two cupcakes. I was excited to try them because they were on cupcake wars, we were truly...read more

 

K-Coast Surf Shop

Nice shop with a wide selection of beach accessories and with good quality. A good contrast is with sunsation, don't mean to bad mouth about the business,...read more

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DEAL!! 10 Min from OC! Dog-Friendly Home — Golf & Ind/Outdoor Pools
Ocean Pines House Rental Picture
  • House Rental Deals and Specials FREE Gym Membership ($64)
  • bedrooms 3
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $169 - $259 /nt
    $800 - $1,400 /wk
 
 
 
 
 

4 reviews write a review

DEAL!! Newly-Renovated Canalfront Home — WiFi, Pools, Tennis, Golf
Ocean Pines House Rental Picture
  • House Rental Deals and Specials OCMD Golf Discounts ($40)
  • bedrooms 4
  • community
  • rental type House
  • sleeps 10
  • baths
  • rates (USD) $149 - $299 /nt
    $995 - $1,495 /wk
 
 
 
 
 

1 reviews write a review

DEAL!! Upscale Marina Home — 10-Min from OCMD, Pools, Tennis, Golf
Ocean Pines Townhome Rental Picture
  • Townhome Rental Deals and Specials OCMD Golf Discounts ($40)
  • bedrooms 3
  • community Ocean Pines N. Gate
  • rental type Townhome
  • sleeps 8
  • baths
  • rates (USD) $120 - $319 /nt
    $600 - $1,595 /wk
 
 
 
 
 

2 reviews write a review

L@@K, Gorgeous, 2 Masters, Late Summer/Fall Specials!!!
Ocean Pines House Rental Picture
  • bedrooms 4
  • community Ocean Pines
  • rental type House
  • sleeps 13
  • baths
  • rates (USD) $165 - $315 /nt
    $900 - $2,200 /wk
 
 
 
 
 

3 reviews write a review

4 Bedroom Single Home Close to Ocean City
Ocean Pines House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 2
  • rates (USD) $75 - $150 /nt
    $400 - $1,150 /wk
    $800 - $4,380 /mth
 
 
 
 
 

3 reviews write a review

Ocean Pines Vacation Rental
Ocean Pines House Rental Picture
  • bedrooms 3
  • community Ocean Pines N. Gate
  • rental type House
  • sleeps 7
  • baths 2
  • rates (USD) $85 - $100 /nt
    $600 - $825 /wk
 
 
 
 
 

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Live, Laugh & Love at the Beach
Ocean Pines House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 7
  • baths 2
  • rates (USD) $71 - $188 /nt
    $500 - $915 /wk
    $880 - $3,200 /mth
 
 
 
 
 

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Charm, Comfort and Spectacular Water Front Views -- near OC Beaches.
Ocean Pines Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • sleeps 8
  • baths 2
  • rates (USD) $200 /nt
 
 
 
 
 

6 reviews write a review

Waterfront Elegance With Spectacular Ocean City Skyline Views, Private Dock
Ocean Pines House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 12
  • baths 3
  • rates (USD) $250 - $329 /nt
    $1,700 - $2,300 /wk
 
 
 
 
 

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