Vacation Rentals in Ocean Pines, Maryland

50 Properties Available

Luxury Waterfront Retreat, Private Dock, Pontoon Option, Golf, Pools, Beach Club Private vacation home
Luxury Waterfront Retreat, Private Dock, Pontoon Option, Golf, Pools, Beach Club
$1907 / night
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Huge Waterfront 6BR\/5.5BA\/Elevator\/4 Decks\/5 Stars\/Superbly Equipped\/Price drop\n Private vacation home
Huge Waterfront 6BR\/5.5BA\/Elevator\/4 Decks\/5 Stars\/Superbly Equipped\/Price drop\n
$1372 / night
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Cozy home featuring a screened-in porch and access to a refreshing pool. Your oasis awaits!! Private vacation home
Cozy home featuring a screened-in porch and access to a refreshing pool. Your oasis awaits!!
$974 / night
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Waterfront Home with views of OC Skyline! Private vacation home
Waterfront Home with views of OC Skyline!
$865 / night
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Waterfront home with sunrise\/sunset views, chef's kitchen, & outdoor areas Private vacation home
Waterfront home with sunrise\/sunset views, chef's kitchen, & outdoor areas
$628 / night
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15% off 5 nights or more Private vacation home
15% off 5 nights or more
$608 / night
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Family friendly chalet, 5 mins. to pools, 12 mins. to beach - 4 beds, 2 baths Private vacation home
Family friendly chalet, 5 mins. to pools, 12 mins. to beach - 4 beds, 2 baths
$534 / night
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Serenity in Ocean Pines | 1 Story Home with Backyard Grill Private vacation home
Serenity in Ocean Pines | 1 Story Home with Backyard Grill
$514 / night
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Private Oasis - Private Pool, 4 Bedrooms, 2.5 baths, Sleeps 11, Non Group Rental Private vacation home
Private Oasis - Private Pool, 4 Bedrooms, 2.5 baths, Sleeps 11, Non Group Rental
$500 / night
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Living ,dining ,family rooms for large families\nLarge driveway.EV car charging Private vacation home
Living ,dining ,family rooms for large families\nLarge driveway.EV car charging
$498 / night
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Tree Top Bliss -Ocean Pines, Dog friendly sleeps 8 Private vacation home
Tree Top Bliss -Ocean Pines, Dog friendly sleeps 8
$484 / night
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A Wave From it All | Screened Porch Outdoor Dining Private vacation home
A Wave From it All | Screened Porch Outdoor Dining
$461 / night
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Canal-side charmer with park views & deck + pool and sports court access Private vacation home
Canal-side charmer with park views & deck + pool and sports court access
$458 / night
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Summer Breeze - Waterfront Cottage For Rent Private vacation home
Summer Breeze - Waterfront Cottage For Rent
$444 / night
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116 Pine Forest Drive in Ocean Pines is a Fabulous Family Retreat, AND you can b Private vacation home
116 Pine Forest Drive in Ocean Pines is a Fabulous Family Retreat, AND you can b
$418 / night
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Enjoy Beautiful Views From This 3 BR 2 BA Home on Quiet Canal in Ocean Pines. Private vacation home
Enjoy Beautiful Views From This 3 BR 2 BA Home on Quiet Canal in Ocean Pines.
$379 / night
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Family Getaway in Peaceful Ocean Pines Private vacation home
Family Getaway in Peaceful Ocean Pines
$374 / night
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Reduced Family Rates 3BR, 2BA, 5 Pools, Back Yard, Private Ocean Beach Club, Sleeps 8, Free Tickets Private vacation home
Reduced Family Rates 3BR, 2BA, 5 Pools, Back Yard, Private Ocean Beach Club, Sleeps 8, Free Tickets
$368 / night
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Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in Private vacation home
Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in
$367 / night
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2 Mi to Golf: Hot Tub Hideaway in Ocean Pines Private vacation home
2 Mi to Golf: Hot Tub Hideaway in Ocean Pines
$363 / night
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Newly renovated, minutes from Ocean City, Assategue Island, & Ocean Downs Casino Private vacation home
Newly renovated, minutes from Ocean City, Assategue Island, & Ocean Downs Casino
$361 / night
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5 Bedroom 3 bath Home in Ocean Pines Private vacation home
5 Bedroom 3 bath Home in Ocean Pines
$355 / night
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Charming House in a Beach Town Community! Private vacation home
Charming House in a Beach Town Community!
$353 / night
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Charming Getaway with Boat Dock Minutes from Ocean City Private vacation home
Charming Getaway with Boat Dock Minutes from Ocean City
$324 / night
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Adorable beach cottage Private vacation home
Adorable beach cottage
$316 / night
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Cozy house in Ocean pines, only 10 mins away from Ocean City. Private vacation home
Cozy house in Ocean pines, only 10 mins away from Ocean City.
$304 / night
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Waterfront townhome with deck, sunroom, amazing bay view & pool Private vacation home
Waterfront townhome with deck, sunroom, amazing bay view & pool
$301 / night
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Patio, Pool Access! Coastal Ocean Pines Cottage Cottage
Patio, Pool Access! Coastal Ocean Pines Cottage
$298 / night
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Renovated Coastal Getaway with Pools, Golf, Tennis, Boat Launch & Beach Club Private vacation home
Renovated Coastal Getaway with Pools, Golf, Tennis, Boat Launch & Beach Club
$294 / night
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Fantastic gem near the beach with fast WiFi, shared pool, grill, central AC & WD Private vacation home
Fantastic gem near the beach with fast WiFi, shared pool, grill, central AC & WD
$289 / night
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Beautiful Ocean Pines home with screened porch, grill & fully stocked kitchen Private vacation home
Beautiful Ocean Pines home with screened porch, grill & fully stocked kitchen
$287 / night
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Home on canal with views, pool\/tennis access, spacious deck & lovely interior Private vacation home
Home on canal with views, pool\/tennis access, spacious deck & lovely interior
$273 / night
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Rabbit Run-Located in the heart of Ocean Pines! Minutes away from OC! Private vacation home
Rabbit Run-Located in the heart of Ocean Pines! Minutes away from OC!
$271 / night
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Quiet family home- Deck, Trails & Water Sports Private vacation home
Quiet family home- Deck, Trails & Water Sports
$264 / night
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Pool + Bay Access! Home 13 Mi to Ocean City Beach Private vacation home
Pool + Bay Access! Home 13 Mi to Ocean City Beach
$260 / night
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Private Dock, Hot Tub: Waterfront Ocean Pines Home Private vacation home
Private Dock, Hot Tub: Waterfront Ocean Pines Home
$260 / night
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Ocean Pines 3 BR 2 Bath Screened Porch Central AC Private vacation home
Ocean Pines 3 BR 2 Bath Screened Porch Central AC
$254 / night
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Dog-friendly, waterfront home with dock, fireplace, pools & great location Private vacation home
Dog-friendly, waterfront home with dock, fireplace, pools & great location
$252 / night
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Modern and Updated Home in Ocean Pines- Oceans Calling only 8 miles away. Private vacation home
Modern and Updated Home in Ocean Pines- Oceans Calling only 8 miles away.
$252 / night
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Cozy home in Ocean Pines minutes away from beach, golf and more Private vacation home
Cozy home in Ocean Pines minutes away from beach, golf and more
$244 / night
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Quiet coastal retreat, minutes from Ocean City, MD beaches, full kitchen. Apartment
Quiet coastal retreat, minutes from Ocean City, MD beaches, full kitchen.
$241 / night
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Updated 3 Bedroom 2 Bathroom Home - Ocean Pines Private vacation home
Updated 3 Bedroom 2 Bathroom Home - Ocean Pines
$233 / night
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OCEAN CITY MD BEACH HOUSE OCEAN PINES MD Private vacation home
OCEAN CITY MD BEACH HOUSE OCEAN PINES MD
$231 / night
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Waterfront Home with Boat Dock and Great Amenities Private vacation home
Waterfront Home with Boat Dock and Great Amenities
$227 / night
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3BR Resort-View Condo w\/ Private BBQ & Parking Apartment
3BR Resort-View Condo w\/ Private BBQ & Parking
$222 / night
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Spacious golf course home, with screened in porch and beach access. Private vacation home
Spacious golf course home, with screened in porch and beach access.
$215 / night
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Spacious Home, With Dock, Sleeps 9, Access To Beach Club & Pool Private vacation home
Spacious Home, With Dock, Sleeps 9, Access To Beach Club & Pool
$206 / night
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Pet friendly 2 Bedroom Townhouse on a Golf Course Private vacation home
Pet friendly 2 Bedroom Townhouse on a Golf Course
$199 / night
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Eastern Shore Getaway with Screened Porch, WiFi & Access to 5 Pools & Beach Club Private vacation home
Eastern Shore Getaway with Screened Porch, WiFi & Access to 5 Pools & Beach Club
$197 / night
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Reasonably Priced Family- Friendly Home, Sleeps 7 Private vacation home
Reasonably Priced Family- Friendly Home, Sleeps 7
$196 / night
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