Ocean Pines Vacation House Rentals

Top-Rated Vacation Rentals in Ocean Pines, MD

Book a vacation rental in Ocean Pines that has the highest visitor rating. Here are 6 of the best vacation rentals in Ocean Pines.
Nautical Lane 146 in popular Montego Bay
10

Excellent

·
House
·
4 br
·
Sleeps 10
·
Swimming Pool · Oven · Furnished ·
From
$228/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Swimming Pool
Oven
Furnished
Air Conditioning
Dishwasher
Wifi
Pool
On Site Laundry
Other spaces
Kitchen
Price drop
Hidden Gem! Just minutes to O.C. & Fenwick
10

Excellent

·
House
·
2 br
·
Sleeps 10
·
Dishwasher · Workspace · Smoking Allowed ·
From
$212/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Dishwasher
Smoking Allowed
Air Conditioning
Pool
Swimming Pool
Wifi
Oven
On Site Laundry
Other spaces
Workspace, Kitchen, Balcony
Price drop
Midtown location with the best views in Ocean City, MD.
10

Excellent

·
House
·
4 br
·
Sleeps 12
·
Waterfront · Wifi · Lake ·
From
$350/night
Check availability
Property
House · 4 Beds · 5 baths
Amenities
Waterfront
Wifi
Lake
Oven
Dishwasher
Air Conditioning
Swimming Pool
Pool
Other spaces
Kitchen, Balcony
Island style beach cottage
10

Excellent

·
House
·
3 br
·
Sleeps 8
·
Furnished · Oven · Kitchen ·
From
$500/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Furnished
Oven
Air Conditioning
On Site Laundry
Dishwasher
Wifi
Beach
Other spaces
Kitchen
Price drop
Large Townhome w/ Lots of Space and Outdoor Pool
10

Excellent

·
House
·
3 br
·
Sleeps 8
·
Swimming Pool · Oven · Kitchen ·
From
$245/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Swimming Pool
Oven
Wifi
Air Conditioning
Dishwasher
On Site Laundry
Package Service
Pool
Other spaces
Kitchen
Price drop
Cotton Patch Hills haven with pool/hot tub, pool table, beach access & fast WiFi
10

Excellent

·
House
·
6 br
·
Sleeps 12
·
Pool · Furnished · Air Conditioning ·
From
$437/night
Check availability
Property
House · 6 Beds · 5 baths
Amenities
Pool
Furnished
Air Conditioning
Fireplace
Swimming Pool
Beach
Wifi
Elevator
Other spaces
Balcony, Kitchen

Our Recommended Vacation Rentals in Ocean Pines, MD

We analyzed vacation rentals in Ocean Pines from many property providers including but not limited to VRBO, Booking.com, Evolve, Blueground and more. We're providing our top recommended offers on the best vacation rentals in Ocean Pines to help you find a deal for your next trip.
Price drop
Ocean Colony 14 in Midtown Ocean City!

No rating

·
House
·
4 br
·
Sleeps 12
·
Wifi · Swimming Pool · Pool ·
From
$437/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Wifi
Swimming Pool
Pool
Residents Lounge
Air Conditioning
Waterfront
Beach
Oven
Other spaces
Kitchen, Balcony
Price drop
Yellow Bird 7 - A 3 Level Townhome in the Heart of Ocean City, MD!

No rating

·
House
·
3 br
·
Sleeps 10
·
Dishwasher · Air Conditioning · Assigned Parking ·
From
$203/night
Check availability
Property
House · 3 Beds · 4 baths
Amenities
Dishwasher
Air Conditioning
Assigned Parking
On Site Laundry
Oven
Furnished
Wifi
Other spaces
Kitchen, Balcony
Town of Millville --- 32669 Cedar Drive | House in Millville

No rating

·
House
·
4 br
·
Sleeps 11
·
Outdoor Space · Kitchen · Assigned Parking ·
From
$361/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Assigned Parking
Air Conditioning
Dishwasher
Oven
On Site Laundry
Furnished
Other spaces
Kitchen

Budget-Friendly Vacation Rentals in Ocean Pines, MD

Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Ocean Pines starting at $27. Use the price filter at the top of the page to search for more specific prices.
$800 - 1 Bedroom in a Shared 5 Bedroom House In Millsboro With Great Amenities

No rating

·
House
·
1 br
·
Storage · On Site Laundry · Deck ·
From
$27/night
Min stay: 30 nights
Property
House · 1 Bed · 1 bath
Amenities
Storage
On Site Laundry
Hardwood Floor
Central Heat
Air Conditioning
Assigned Parking
Other spaces
Deck
Blair Isle Beauty
7.4

Very good

·
House
·
2 br
·
Sleeps 6
·
Outdoor Space · Balcony · Waterfront ·
From
$60/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Waterfront
Air Conditioning
Oven
Furnished
Dishwasher
On Site Laundry
Wifi
Ocean
Other spaces
Balcony, Kitchen
Price drop
Oceanfront Condo with Beach Views, Enclosed Balcony, WiFi, AC & Shared Pool
10

Excellent

·
House
·
1 br
·
Sleeps 6
·
Air Conditioning · Furnished · In Unit Laundry ·
From
$65/night
Check availability
Property
House · 1 Bed · 2 baths
Amenities
Air Conditioning
Furnished
In Unit Laundry
Beach
Dishwasher
Wifi
Oven
Swimming Pool
Other spaces
Kitchen, Balcony
Sails II
7.7

Very good

·
House
·
1 br
·
Sleeps 6
·
Swimming Pool · Elevator · Kitchen ·
From
$65/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Swimming Pool
Elevator
Air Conditioning
Wifi
Waterfront
Ocean
On Site Laundry
Dishwasher
Other spaces
Kitchen, Balcony
Wight Bay
7.4

Very good

·
House
·
2 br
·
Sleeps 6
·
Kitchen · Dishwasher · Pool ·
From
$65/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Dishwasher
Pool
Elevator
Air Conditioning
Swimming Pool
On Site Laundry
Furnished
Oven
Other spaces
Kitchen, Balcony
Price drop
Cozy Family-Friendly Home with WiFi, AC, Shared Pool, Tennis, Pond & Playgrounds
10

Excellent

·
House
·
2 br
·
Sleeps 6
·
Swimming Pool · Pool · In Unit Laundry ·
From
$69/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Swimming Pool
Pool
In Unit Laundry
Furnished
On Site Laundry
Wifi
Dishwasher
Free Parking
Other spaces
Kitchen

Vacation Rentals With AC and/or Heat in Ocean Pines, MD

Whether you need air conditioning or central heating, these vacation rentals are for you.
Comfortable Ocean City Retreat w/ Yard & Deck

No rating

·
House
·
4 br
·
Sleeps 11
·
Kitchen · Assigned Parking · Workspace ·
From
$150/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Assigned Parking
Central Heat
Fireplace
Dishwasher
On Site Laundry
Wifi
Microwave
Cable
Other spaces
Kitchen, Workspace, Garden
Updated Ocean City Home w/ Dock Access & Yard
10

Excellent

·
House
·
4 br
·
Sleeps 12
·
Assigned Parking · Central Heat · Microwave ·
From
$295/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Assigned Parking
Central Heat
Microwave
Air Conditioning
Wifi
Walk In Closets
Ceiling Fan
Toiletries
Other spaces
Kitchen, Workspace
Dog-Friendly Ocean Pines Home w/ Pool Access!
9.8

Excellent

·
House
·
2 br
·
Sleeps 3
·
Air Conditioning · Assigned Parking · Kitchen ·
From
$88/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Air Conditioning
Assigned Parking
Pool
Ceiling Fan
On Site Laundry
Central Heat
Wifi
Oven
Other spaces
Kitchen, Garden

Family-Friendly Vacation Rentals in Ocean Pines, MD

Heading to Ocean Pines for your next family vacation? Check out these family-friendly vacation rentals, which have more bedrooms and more space for you and your loved ones. Use the filters at the top of the page to narrow your search and find what you need.
Mallard Lakes -- 158 Cardinal
10

Excellent

·
House
·
1 br
·
Sleeps 4
·
Fireplace · Kitchen · Outdoor Space ·
From
$286/night
Check availability
Property
Apartment · 1 Bed · 2 baths
Amenities
Fireplace
Air Conditioning
Hot Tub
Oven
Dishwasher
Furnished
Swimming Pool
On Site Laundry
Other spaces
Kitchen
Price drop
47 Oyster Bay Dr

No rating

·
House
·
Studio
·
Sleeps 8
·
Assigned Parking · Wifi · Outdoor Space ·
From
$612/night
Check availability
Property
Apartment · Studio · 3 baths
Amenities
Assigned Parking
Wifi
On Site Laundry
Furnished
Air Conditioning
Dishwasher
Other spaces
Kitchen
Price drop
Diamond Head Condos
7

Very good

·
House
·
1 br
·
Sleeps 6
·
Outdoor Space · Pool · Dishwasher ·
From
$182/night
Check availability
Property
Apartment · 1 Bed · 2 baths
Amenities
Pool
Dishwasher
Swimming Pool
Waterfront
Air Conditioning
Ocean
Oven
Wifi
Other spaces
Balcony, Kitchen
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Updated: September 21, 2023