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Holiday Rentals in Ocean Pines

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92 rentals in Ocean Pines.
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Newly Renovated Home With Impressive Views Of The 7Th Green!, holiday rental in Ocean Pines
Newly Renovated Home With Impressive Views Of The 7Th Green!, holiday rental in Ocean Pines
Newly Renovated Home With Impressive Views Of The 7Th Green!, holiday rental in Ocean Pines

Newly Renovated Home With Impressive Views Of The 7Th Green!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Million Dollar View! Waterfront oasis with Ocean City skyline view!, holiday rental in Ocean Pines
Million Dollar View! Waterfront oasis with Ocean City skyline view!, holiday rental in Ocean Pines
Million Dollar View! Waterfront oasis with Ocean City skyline view!, holiday rental in Ocean Pines

Million Dollar View! Waterfront oasis with Ocean City skyline view!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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CANAL FRONT - GREAT VIEWS - 5 BDRM, 3&1/2 BATHS, 2 KINGS, GOLF, RELAX..., holiday rental in Ocean Pines
CANAL FRONT - GREAT VIEWS - 5 BDRM, 3&1/2 BATHS, 2 KINGS, GOLF, RELAX..., holiday rental in Ocean Pines
CANAL FRONT - GREAT VIEWS - 5 BDRM, 3&1/2 BATHS, 2 KINGS, GOLF, RELAX..., holiday rental in Ocean Pines

CANAL FRONT - GREAT VIEWS - 5 BDRM, 3&1/2 BATHS, 2 KINGS, GOLF, RELAX...

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Quiet Beach Home in the Pines Close to Everything, holiday rental in Ocean Pines
Beautiful Quiet Beach Home in the Pines Close to Everything, holiday rental in Ocean Pines
Beautiful Quiet Beach Home in the Pines Close to Everything, holiday rental in Ocean Pines

Beautiful Quiet Beach Home in the Pines Close to Everything

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Refurbished Ocean Pines Cottage with Beach Parking Pass, holiday rental in Ocean Pines
Refurbished Ocean Pines Cottage with Beach Parking Pass, holiday rental in Ocean Pines
Refurbished Ocean Pines Cottage with Beach Parking Pass, holiday rental in Ocean Pines

Refurbished Ocean Pines Cottage with Beach Parking Pass

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Quaint waterfront bungalow just minutes from the beaches of Ocean City, MD, holiday rental in Ocean Pines
Quaint waterfront bungalow just minutes from the beaches of Ocean City, MD, holiday rental in Ocean Pines
Quaint waterfront bungalow just minutes from the beaches of Ocean City, MD, holiday rental in Ocean Pines

Quaint waterfront bungalow just minutes from the beaches of Ocean City, MD

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Superb Direct Waterfront on St. Martin River in Ocean Pines With 2 Dock Slips, holiday rental in Ocean Pines
Superb Direct Waterfront on St. Martin River in Ocean Pines With 2 Dock Slips, holiday rental in Ocean Pines
Superb Direct Waterfront on St. Martin River in Ocean Pines With 2 Dock Slips, holiday rental in Ocean Pines

Superb Direct Waterfront on St. Martin River in Ocean Pines With 2 Dock Slips

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Gorgeous wired waterfront home with magnificent sunset views.  Kayaks included., holiday rental in Ocean Pines
Gorgeous wired waterfront home with magnificent sunset views.  Kayaks included., holiday rental in Ocean Pines
Gorgeous wired waterfront home with magnificent sunset views.  Kayaks included., holiday rental in Ocean Pines

Gorgeous wired waterfront home with magnificent sunset views. Kayaks included.

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Ocean City, MD Area Luxury Big Water View, 6+ BR/5.5 BA Decks/Views/Perfect!

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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Spacious, well maintained, 4br 3bath home overlooking Golf Course., holiday rental in Ocean Pines
Spacious, well maintained, 4br 3bath home overlooking Golf Course., holiday rental in Ocean Pines
Spacious, well maintained, 4br 3bath home overlooking Golf Course., holiday rental in Ocean Pines

Spacious, well maintained, 4br 3bath home overlooking Golf Course.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Dog-Friendly Berlin Home w/ Pool & Water Access!, holiday rental in Ocean Pines
Dog-Friendly Berlin Home w/ Pool & Water Access!, holiday rental in Ocean Pines
Dog-Friendly Berlin Home w/ Pool & Water Access!, holiday rental in Ocean Pines

Dog-Friendly Berlin Home w/ Pool & Water Access!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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waterfront beach retreat with boat dock, holiday rental in Ocean Pines
waterfront beach retreat with boat dock, holiday rental in Ocean Pines
waterfront beach retreat with boat dock, holiday rental in Ocean Pines

waterfront beach retreat with boat dock

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Ocean Pines House w/ Screened-In Deck & Grill!, holiday rental in Ocean Pines
Ocean Pines House w/ Screened-In Deck & Grill!, holiday rental in Ocean Pines
Ocean Pines House w/ Screened-In Deck & Grill!, holiday rental in Ocean Pines

Ocean Pines House w/ Screened-In Deck & Grill!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Salty Air Serenity * 728 Ocean Parkway in Ocean Pines, Maryland, holiday rental in Ocean Pines
Salty Air Serenity * 728 Ocean Parkway in Ocean Pines, Maryland, holiday rental in Ocean Pines
Salty Air Serenity * 728 Ocean Parkway in Ocean Pines, Maryland, holiday rental in Ocean Pines

Salty Air Serenity * 728 Ocean Parkway in Ocean Pines, Maryland

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Scenic Water front secluded house with pier and view of the bay  overlooking OC, holiday rental in Ocean Pines
Scenic Water front secluded house with pier and view of the bay  overlooking OC, holiday rental in Ocean Pines
Scenic Water front secluded house with pier and view of the bay  overlooking OC, holiday rental in Ocean Pines

Scenic Water front secluded house with pier and view of the bay overlooking OC

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Home Away From Home,  pet friendly retreat!, holiday rental in Ocean Pines
Home Away From Home,  pet friendly retreat!, holiday rental in Ocean Pines
Home Away From Home,  pet friendly retreat!, holiday rental in Ocean Pines

Home Away From Home, pet friendly retreat!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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One Level Waterfront Home-Pet Friendly - 5 Pools- Sleeps 8- Self Check-In !, holiday rental in Ocean Pines
One Level Waterfront Home-Pet Friendly - 5 Pools- Sleeps 8- Self Check-In !, holiday rental in Ocean Pines
One Level Waterfront Home-Pet Friendly - 5 Pools- Sleeps 8- Self Check-In !, holiday rental in Ocean Pines

One Level Waterfront Home-Pet Friendly - 5 Pools- Sleeps 8- Self Check-In !

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Ocean Pines / Ocean City Cottage, holiday rental in Ocean Pines
Cozy Ocean Pines / Ocean City Cottage, holiday rental in Ocean Pines
Cozy Ocean Pines / Ocean City Cottage, holiday rental in Ocean Pines

Cozy Ocean Pines / Ocean City Cottage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Enjoy Beautiful Views From This 3 BR 2 BA Home on Quiet Canal in Ocean Pines., holiday rental in Ocean Pines
Enjoy Beautiful Views From This 3 BR 2 BA Home on Quiet Canal in Ocean Pines., holiday rental in Ocean Pines
Enjoy Beautiful Views From This 3 BR 2 BA Home on Quiet Canal in Ocean Pines., holiday rental in Ocean Pines

Enjoy Beautiful Views From This 3 BR 2 BA Home on Quiet Canal in Ocean Pines.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Golf course front home - 4 Bedrooms/3 full baths - 8 separate beds, holiday rental in Ocean Pines
Golf course front home - 4 Bedrooms/3 full baths - 8 separate beds, holiday rental in Ocean Pines
Golf course front home - 4 Bedrooms/3 full baths - 8 separate beds, holiday rental in Ocean Pines

Golf course front home - 4 Bedrooms/3 full baths - 8 separate beds

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious Home, With Dock, Sleeps 9, Access To Beach Club & Pool, holiday rental in Ocean Pines
Spacious Home, With Dock, Sleeps 9, Access To Beach Club & Pool, holiday rental in Ocean Pines
Spacious Home, With Dock, Sleeps 9, Access To Beach Club & Pool, holiday rental in Ocean Pines

Spacious Home, With Dock, Sleeps 9, Access To Beach Club & Pool

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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Enjoy the Peace and Quiet in this Waterfront Ocean Pines Home!, holiday rental in Ocean Pines
Enjoy the Peace and Quiet in this Waterfront Ocean Pines Home!, holiday rental in Ocean Pines
Enjoy the Peace and Quiet in this Waterfront Ocean Pines Home!, holiday rental in Ocean Pines

Enjoy the Peace and Quiet in this Waterfront Ocean Pines Home!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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Beautiful single story home in Ocean Pines., holiday rental in Ocean Pines
Beautiful single story home in Ocean Pines., holiday rental in Ocean Pines
Beautiful single story home in Ocean Pines., holiday rental in Ocean Pines

Beautiful single story home in Ocean Pines.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Coastal Cottage - Charm, Comfort and Spectacular Water Front near OC Beaches, holiday rental in Ocean Pines
Coastal Cottage - Charm, Comfort and Spectacular Water Front near OC Beaches, holiday rental in Ocean Pines
Coastal Cottage - Charm, Comfort and Spectacular Water Front near OC Beaches, holiday rental in Ocean Pines

Coastal Cottage - Charm, Comfort and Spectacular Water Front near OC Beaches

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Waterfront townhome w/deck, sunroom, amazing bay view & shared pool, holiday rental in Ocean Pines
Waterfront townhome w/deck, sunroom, amazing bay view & shared pool, holiday rental in Ocean Pines
Waterfront townhome w/deck, sunroom, amazing bay view & shared pool, holiday rental in Ocean Pines

Waterfront townhome w/deck, sunroom, amazing bay view & shared pool

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Cozy, family friendly cottage, 2 BR, 1 Bath, 10m to Ocean City, pool & clubhouse, holiday rental in Ocean Pines
Cozy, family friendly cottage, 2 BR, 1 Bath, 10m to Ocean City, pool & clubhouse, holiday rental in Ocean Pines
Cozy, family friendly cottage, 2 BR, 1 Bath, 10m to Ocean City, pool & clubhouse, holiday rental in Ocean Pines

Cozy, family friendly cottage, 2 BR, 1 Bath, 10m to Ocean City, pool & clubhouse

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Unique waterfront home w/ shared pools, a furnished deck, & a full kitchen, holiday rental in Ocean Pines
Unique waterfront home w/ shared pools, a furnished deck, & a full kitchen, holiday rental in Ocean Pines
Unique waterfront home w/ shared pools, a furnished deck, & a full kitchen, holiday rental in Ocean Pines

Unique waterfront home w/ shared pools, a furnished deck, & a full kitchen

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Family-friendly home on a wooded lot w/ a loft, deck, & fire pit, holiday rental in Ocean Pines
Family-friendly home on a wooded lot w/ a loft, deck, & fire pit, holiday rental in Ocean Pines
Family-friendly home on a wooded lot w/ a loft, deck, & fire pit, holiday rental in Ocean Pines

Family-friendly home on a wooded lot w/ a loft, deck, & fire pit

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Spacious, two-story home w/full kitchen, balcony & outdoor fire pit, holiday rental in Ocean Pines
Spacious, two-story home w/full kitchen, balcony & outdoor fire pit, holiday rental in Ocean Pines
Spacious, two-story home w/full kitchen, balcony & outdoor fire pit, holiday rental in Ocean Pines

Spacious, two-story home w/full kitchen, balcony & outdoor fire pit

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Reasonably Priced Family- Friendly Home, Sleeps 7, holiday rental in Ocean Pines
Reasonably Priced Family- Friendly Home, Sleeps 7, holiday rental in Ocean Pines
Reasonably Priced Family- Friendly Home, Sleeps 7, holiday rental in Ocean Pines

Reasonably Priced Family- Friendly Home, Sleeps 7

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Ocean Pines House w/ Private Hot Tub 2 Mi to Golf!, holiday rental in Ocean Pines
Ocean Pines House w/ Private Hot Tub 2 Mi to Golf!, holiday rental in Ocean Pines
Ocean Pines House w/ Private Hot Tub 2 Mi to Golf!, holiday rental in Ocean Pines

Ocean Pines House w/ Private Hot Tub 2 Mi to Golf!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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This newly decorated, 4 bedroom 2 ½ bath home is nestled in the woods in North O, holiday rental in Ocean Pines
This newly decorated, 4 bedroom 2 ½ bath home is nestled in the woods in North O, holiday rental in Ocean Pines
This newly decorated, 4 bedroom 2 ½ bath home is nestled in the woods in North O, holiday rental in Ocean Pines

This newly decorated, 4 bedroom 2 ½ bath home is nestled in the woods in North O

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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790 Ocean Parkway, holiday rental in Ocean Pines
790 Ocean Parkway, holiday rental in Ocean Pines
790 Ocean Parkway, holiday rental in Ocean Pines

790 Ocean Parkway

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Family-Friendly Duplex Close to Ocean City Beach w/Shared Pool, WiFI, AC, W/D!, holiday rental in Ocean Pines
Family-Friendly Duplex Close to Ocean City Beach w/Shared Pool, WiFI, AC, W/D!, holiday rental in Ocean Pines
Family-Friendly Duplex Close to Ocean City Beach w/Shared Pool, WiFI, AC, W/D!, holiday rental in Ocean Pines

Family-Friendly Duplex Close to Ocean City Beach w/Shared Pool, WiFI, AC, W/D!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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14 Hickory Way, holiday rental in Ocean Pines
14 Hickory Way, holiday rental in Ocean Pines
14 Hickory Way, holiday rental in Ocean Pines

14 Hickory Way

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Moonraker Road 54-AC, W/D, Free WIFI, holiday rental in Ocean Pines
Moonraker Road 54-AC, W/D, Free WIFI, holiday rental in Ocean Pines
Moonraker Road 54-AC, W/D, Free WIFI, holiday rental in Ocean Pines

Moonraker Road 54-AC, W/D, Free WIFI

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Dog-friendly condo with shared pool plus lake, canal, and golf course views, holiday rental in Ocean Pines
Dog-friendly condo with shared pool plus lake, canal, and golf course views, holiday rental in Ocean Pines
Dog-friendly condo with shared pool plus lake, canal, and golf course views, holiday rental in Ocean Pines

Dog-friendly condo with shared pool plus lake, canal, and golf course views

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Berlin Resort Comm Home - 15 Mins from Ocean City!, holiday rental in Ocean Pines
Berlin Resort Comm Home - 15 Mins from Ocean City!, holiday rental in Ocean Pines
Berlin Resort Comm Home - 15 Mins from Ocean City!, holiday rental in Ocean Pines

Berlin Resort Comm Home - 15 Mins from Ocean City!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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NEW! Cozy Ocean Pines Cottage: Swim, Shop & Golf!, holiday rental in Ocean Pines
NEW! Cozy Ocean Pines Cottage: Swim, Shop & Golf!, holiday rental in Ocean Pines
NEW! Cozy Ocean Pines Cottage: Swim, Shop & Golf!, holiday rental in Ocean Pines

NEW! Cozy Ocean Pines Cottage: Swim, Shop & Golf!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Family-friendly home on canal w/entertainment, dock & free WiFi, holiday rental in Ocean Pines
Family-friendly home on canal w/entertainment, dock & free WiFi, holiday rental in Ocean Pines
Family-friendly home on canal w/entertainment, dock & free WiFi, holiday rental in Ocean Pines

Family-friendly home on canal w/entertainment, dock & free WiFi

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Family Home w/Shared Pool, Private Washer/Dryer, AC, Free WiFi - Close to Beach, holiday rental in Ocean Pines
Family Home w/Shared Pool, Private Washer/Dryer, AC, Free WiFi - Close to Beach, holiday rental in Ocean Pines
Family Home w/Shared Pool, Private Washer/Dryer, AC, Free WiFi - Close to Beach, holiday rental in Ocean Pines

Family Home w/Shared Pool, Private Washer/Dryer, AC, Free WiFi - Close to Beach

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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New SFH, Close to Beaches, Golf, Pool, Casinos and More, holiday rental in Ocean Pines
New SFH, Close to Beaches, Golf, Pool, Casinos and More, holiday rental in Ocean Pines
New SFH, Close to Beaches, Golf, Pool, Casinos and More, holiday rental in Ocean Pines

New SFH, Close to Beaches, Golf, Pool, Casinos and More

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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AUG 29th - SEPT 2nd STILL AVAILABLE near Ocean City/Assateague National Seashore, holiday rental in Ocean Pines
AUG 29th - SEPT 2nd STILL AVAILABLE near Ocean City/Assateague National Seashore, holiday rental in Ocean Pines
AUG 29th - SEPT 2nd STILL AVAILABLE near Ocean City/Assateague National Seashore, holiday rental in Ocean Pines

AUG 29th - SEPT 2nd STILL AVAILABLE near Ocean City/Assateague National Seashore

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Private and pet-friendly in OP, holiday rental in Ocean Pines
Private and pet-friendly in OP, holiday rental in Ocean Pines
Private and pet-friendly in OP, holiday rental in Ocean Pines

Private and pet-friendly in OP

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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NEW! Charming Getaway, 9 Mi to Ocean City Beach!, holiday rental in Ocean Pines
NEW! Charming Getaway, 9 Mi to Ocean City Beach!, holiday rental in Ocean Pines
NEW! Charming Getaway, 9 Mi to Ocean City Beach!, holiday rental in Ocean Pines

NEW! Charming Getaway, 9 Mi to Ocean City Beach!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Boaters DREAM with SPECTACULAR views of the OC skyline!, holiday rental in Ocean Pines
Boaters DREAM with SPECTACULAR views of the OC skyline!, holiday rental in Ocean Pines
Boaters DREAM with SPECTACULAR views of the OC skyline!, holiday rental in Ocean Pines

Boaters DREAM with SPECTACULAR views of the OC skyline!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Adorable beach cottage, holiday rental in Ocean Pines
Adorable beach cottage, holiday rental in Ocean Pines
Adorable beach cottage, holiday rental in Ocean Pines

Adorable beach cottage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront getaway in a quiet neighborhood w/ free WiFi, dock, & furnished deck, holiday rental in Ocean Pines
Waterfront getaway in a quiet neighborhood w/ free WiFi, dock, & furnished deck, holiday rental in Ocean Pines
Waterfront getaway in a quiet neighborhood w/ free WiFi, dock, & furnished deck, holiday rental in Ocean Pines

Waterfront getaway in a quiet neighborhood w/ free WiFi, dock, & furnished deck

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Charming Waterfront Beach home near Ocean City, holiday rental in Ocean Pines
Charming Waterfront Beach home near Ocean City, holiday rental in Ocean Pines
Charming Waterfront Beach home near Ocean City, holiday rental in Ocean Pines

Charming Waterfront Beach home near Ocean City

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Endless Summer, water front oasis, holiday rental in Ocean Pines
Endless Summer, water front oasis, holiday rental in Ocean Pines
Endless Summer, water front oasis, holiday rental in Ocean Pines

Endless Summer, water front oasis

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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