Compare Vacation Rentals & Airbnb in Ocean Pines, MD

481 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Ocean Pines, MD vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

481 Rentals and Airbnb in Ocean Pines, MD

Best family friendly Ocean Pines, MD vacation rentals

Among the 481 accommodations in Ocean Pines, MD, here are the 4 best family friendly rentals

Wilmington Terrace - Ocean Pines, MD
9.0 402 reviews
Ocean Pines, MD
25/08 – 31/08
$367/nighttotal: $2202 (6 )

Wilmington Terrace

1 2
studio , Ocean City
This Ocean City apartment is ideally located just a short walk from the beach and town centre, putting you right in the heart of the action. It has received excellent ratings for location, cleanliness and overall experience, ensuring a comfortable and enjoyable stay. The apartment is well-equipped with modern amenities and a spacious layout, perfect for families or groups of friends. You'll have access to a range of facilities including a swimming pool, jacuzzi, terrace, garden, spa, bar, parking and free Wi-Fi, making it easy to relax and enjoy your time in Ocean City.
Home Away From Home,  Pet Friendly Retreat! - Ocean Pines, MD
9.7 175 reviews
Ocean Pines, MD
25/08 – 31/08
$644/nighttotal: $3864 (6 )

Home Away From Home, Pet Friendly Retreat!

3 2
apartment , Ocean Pines
This holiday home is located in Ocean Pines, just 1.3 kilometres from Isle of Wight Bay and within a 5-kilometre radius of Casino at Ocean Downs and River Run Golf Club, offering easy access to the area's main attractions. The property has received excellent ratings for location, cleanliness and overall experience.
The property has three bedrooms and two bathrooms, comfortably accommodating up to six guests. The home offers a range of amenities, including a fully equipped kitchen, a private garden, a terrace, air conditioning, Wi-Fi, and parking.
2 Mi To Ocean City Boardwalk Gem With Pool And Marina - Ocean Pines, MD
9.3 78 reviews
Ocean Pines, MD
25/08 – 31/08
$462/nighttotal: $2772 (6 )

2 Mi To Ocean City Boardwalk Gem With Pool And Marina

1 2
apartment , Ocean City
This Ocean City apartment is perfectly situated in the heart of the town, just a short 5-minute walk from Ocean City Beach and less than a mile from Assateague Beach, offering easy access to a variety of beach experiences. The apartment has consistently received excellent ratings for its location, cleanliness, and overall experience.
The one-bedroom apartment, spanning 63 square metres, comfortably accommodates up to 2 guests. Enjoy a range of amenities including a fully equipped kitchen, a private balcony, a swimming pool, a spa, and free Wi-Fi, ensuring a relaxing and enjoyable stay.
Hi-a-tus A-frame - Ocean Pines, MD
10 52 reviews
Ocean Pines, MD
05/09 – 12/09
$444/nighttotal: $3108 (7 )

Hi-a-tus A-frame

2 2
apartment , Ocean Pines
This charming A-frame lodge is situated in Ocean Pines, just 10 kilometres from Ocean City and 15 kilometres from Assateague Island, offering easy access to both the bustling city and the serene nature of the island. The property consistently receives excellent ratings from previous guests for its cleanliness, location, and overall experience.
The lodge has an open-plan layout, comfortably accommodating up to four guests in its two bedrooms and one bathroom. Guests can enjoy a range of amenities, including a swimming pool, Jacuzzi, garden, and parking, as well as access to the community's five pools, playgrounds, yacht club, and farmers market.

Best Ocean Pines, MD vacation rentals with a pool

Among the 481 accommodations in Ocean Pines, MD, here are the 4 best rentals with a pool

Quiet Coastal Retreat, Minutes From Ocean City, Md, Full Kitchen. - Ocean Pines, MD
10 2 reviews
Ocean Pines, MD
13/07 – 17/07
$357/nighttotal: $1428 (4 )

Quiet Coastal Retreat, Minutes From Ocean City, Md, Full Kitchen.

1 2
apartment , Ocean Pines
This Ocean Pines apartment, near Berlin, Maryland, offers easy access to Ocean City and Assateague Island, both within a few kilometres.
The 52-square-metre self-catering flat features one bedroom, one bathroom, sleeps two guests, and includes a kitchen with a fridge, microwave, and dishwasher, plus a swimming pool and parking.
Spacious Ocean Pines Home W/deck, Grill, Fire Pit, Games, Wifi, Wash/dryer & Ac - Ocean Pines, MD
Ocean Pines, MD
06/07 – 09/07
$548/nighttotal: $1644 (3 )

Spacious Ocean Pines Home W/deck, Grill, Fire Pit, Games, Wifi, Wash/dryer & Ac

3 3
apartment , Ocean Pines
This apartment is located in the Ocean Pines community in Berlin, Maryland, offering easy access to the coast, amusement parks such as Jolly Roger Amusement Park, and local attractions.
This 147 square metre flat sleeps eight guests and features three bedrooms, two bathrooms, a well-equipped kitchen, central air conditioning, a game room, a spacious deck with outdoor seating and a fire pit, and access to community amenities including five swimming pools, parks, a beach club, marina, golf course, and tennis courts.
Seaside Retreat 405 - Ocean Pines, MD
9.7 47 reviews
Ocean Pines, MD
18/07 – 25/07
$712/nighttotal: $4984 (7 )

Seaside Retreat 405

1 6
apartment , Ocean City
Seaside Retreat, a spacious Ocean City apartment, is situated a short walk (approx. 1.9km) from Northside Park and Fenwick Island State Park Beach, and within a reasonable driving distance (9.3km) of the Roland E. Powell Convention Center and the Ocean City Boardwalk.
This 160 square metre, three-bedroom, three-bathroom dwelling boasts a fully equipped kitchen, private balcony with sea views, free Wi-Fi, and access to an on-site swimming pool, spa, fitness centre, and children's playground, comfortably accommodating families or groups.
Charming Pines Home: Garage, Ac, Clean & Family Ready! - Ocean Pines, MD
9.6 4 reviews
Ocean Pines, MD
01/08 – 08/08
$614/nighttotal: $4298 (7 )

Charming Pines Home: Garage, Ac, Clean & Family Ready!

3 3
apartment , Ocean Pines
This South Ocean Pines flat is located in coastal Maryland, a short distance from Ocean City Beach and Jolly Roger Amusement Park.
This 142 square metre residence offers three bedrooms, two bathrooms, and a guest capacity of eight, featuring a full kitchen, air conditioning, free WiFi, and a communal swimming pool, with a sunroom that can serve as an additional sleeping area.

Frequently Asked Questions about vacation rentals in Ocean Pines, MD

  • What are some interesting places to visit in or near Ocean Pines, MD?

    Ocean Pines is a great base for exploring the area. You can visit Assateague Island National Seashore, just a short drive away, to see wild horses and enjoy the beach. Or, head to the charming town of Berlin, a short drive away, and explore its historic downtown with its shops and restaurants.
  • What are the best Airbnb and vacation rentals in Ocean Pines, MD?

    Sunset Island, 28th St Bayside - Very Affordable And Pet Friendly and Waterfront Townhouse Gorgeous Sunsets 2 Decks On Water are the most popular Airbnb and vacation rentals in Ocean Pines, MD among travelers.

  • Which walking or cycling routes are the best in Ocean Pines, MD?

    Ocean Pines has a great network of walking and cycling paths. The Ocean Pines Boardwalk is a popular choice for a leisurely stroll, while the Ocean Pines Golf Course offers scenic views for a longer bike ride. If you're looking for a more challenging ride, try the Assateague Island Loop Trail.
  • What are the most popular Airbnbs in Ocean Pines, MD?

  • What sports or outdoor activites can visitors enjoy in and around Ocean Pines, MD?

    Ocean Pines is a great place for watersports, with plenty of opportunities for swimming, boating, and fishing. You can also enjoy golfing at the Ocean Pines Golf Club or go for a hike or bike ride in the surrounding area. There are also plenty of opportunities for birdwatching, especially around the Assateague Island National Seashore.
  • What are the best vacation rentals with a pool in Ocean Pines, MD?

    Sunset Island, Waterfront Townhouse Gorgeous Sunsets 2 Decks On Water and Wight Bay Unit 245 are the best vacation rentals with a pool in Ocean Pines, MD.

  • What other towns or cities can be easily accessed from Ocean Pines, MD?

    Ocean City is just a short drive away, and it's a bustling beach town with lots of shops, restaurants, and nightlife. If you're looking for something a bit quieter, you could visit Berlin, a charming town with a historic downtown area. And of course, you can always take a trip to Assateague Island National Seashore, which is just a short drive from Ocean Pines.
  • What are the best rentals for families and kids in Ocean Pines, MD?

  • What amenities are commonly available in vacation rentals in Ocean Pines, MD?

    Most vacation rentals in Ocean Pines offer the basics, like a kitchen, bathroom, and bedrooms. Many also have amenities like swimming pools, hot tubs, and private decks. If you're looking for something specific, be sure to check the listing carefully.
  • What are the best rentals or Airbnbs with a jacuzzi in Ocean Pines, MD?

  • What time of year is best to rent a vacation rental Ocean Pines, MD?

    The best time to visit Ocean Pines depends on your preferences. Summer is the most popular time to visit, with warm weather and plenty of sunshine. If you prefer milder weather and fewer crowds, spring or autumn are great options.
  • What are the local dishes in Ocean Pines, MD region?

    The Eastern Shore of Maryland is known for its fresh seafood. Try a crab cake sandwich, a classic Maryland dish, or enjoy some steamed blue crabs with Old Bay seasoning. You can also find delicious oysters, clams, and fish at many local restaurants.

Destinations nearby

Best Ocean Pines, MD vacation rentals with a balcony

Crystal Sands Apartments - Ocean Pines, MD
8.9 52 reviews
Ocean Pines, MD
13/07 – 17/07
$446/nighttotal: $1784 (4 )

Crystal Sands Apartments

1 2
apartment , Ocean City
Crystal Sands Apartments offer family-friendly self-catering accommodation in a central Ocean City location, a 0.97 km stroll from Ocean City Beach and within 2.25 km of Ripley's Believe It Or Not! and the Ocean City Boardwalk.
These Ocean City apartments feature free Wi-Fi, private parking, and some units boast balconies; all include air conditioning and private bathrooms, perfect for families or couples seeking a relaxing beach holiday (bachelor/hen parties are not permitted).
Beachhaven 305-oceanblock 40th St, Free Wifi, Ac - Ocean Pines, MD
8.0 2 reviews
Ocean Pines, MD
13/07 – 17/07
$534/nighttotal: $2136 (4 )

Beachhaven 305-oceanblock 40th St, Free Wifi, Ac

1 2
apartment , Ocean City
This one-bedroom flat offers direct ocean views from its balcony, situated on the ocean block of 40th Street in Midtown Ocean City, just a short 150-metre walk to the beach and conveniently located opposite the Convention Centre with EV charging stations.
This apartment, accommodating up to six guests, features a private swimming pool, a kitchen with a fridge and microwave oven, air conditioning, and is within easy reach of Jolly Roger Amusement Park.
Cute Beach Condo - Walking Distance To The Beach And Boardwalk! - Ocean Pines, MD
8.2 44 reviews
Ocean Pines, MD
05/09 – 12/09
$287/nighttotal: $2009 (7 )

Cute Beach Condo - Walking Distance To The Beach And Boardwalk!

1 2
apartment , Ocean City
This one-bedroom apartment is conveniently located in Downtown Ocean City, just 800 metres from the beach, boardwalk, and Isle of Wight Bay. It has received very good ratings from previous guests.
The flat comfortably sleeps four people and includes a kitchen with a fridge and microwave. Guests can enjoy a private pool, a shared outdoor pool, and a terrace or balcony.
Oceanfrontstudio-slps4-pool-pickleball-hbomax-dis+ - Ocean Pines, MD
9.9 162 reviews
Ocean Pines, MD
01/08 – 08/08
$620/nighttotal: $4340 (7 )

Oceanfrontstudio-slps4-pool-pickleball-hbomax-dis+

2 3
studio , Ocean City
This oceanfront studio apartment in the Golden Sands building, North Ocean City, Maryland, offers stunning direct ocean views and is a short drive (approximately 1.6km) from Northside Park and the Ocean City boardwalk.
The 1-bedroom, 1-bathroom apartment sleeps 4 guests, features a full kitchen with stainless steel appliances, a private balcony, access to a swimming pool, fitness centre and sauna, plus amenities including HBO Max and Disney+ streaming, and a washer/dryer.

Best Ocean Pines, MD vacation rentals with parking

*New Listing* Oceanblock 2br/2ba Condo With 2 Parking Spots. - Ocean Pines, MD
9.7 83 reviews
Ocean Pines, MD
05/09 – 12/09
$451/nighttotal: $3157 (7 )

*New Listing* Oceanblock 2br/2ba Condo With 2 Parking Spots.

2 2
apartment , Ocean City
This Ocean City apartment is located just 1.6 kilometres from Assawoman Bay and Ocean City Beach, and 4.5 kilometres from the Ocean City Boardwalk, offering easy access to the area's attractions. It has received excellent ratings for location, cleanliness, and overall experience.
The apartment has two bedrooms and two bathrooms, comfortably accommodating up to six guests within its 89 square metre space. It offers a range of amenities, including a fully equipped kitchen, a swimming pool, a terrace, a garden, and free Wi-Fi.
Serene Sunrise & Shimmering Skyline. 5 Star Hosts - Ocean Pines, MD
9.9 74 reviews
Ocean Pines, MD
13/07 – 17/07
$1687/nighttotal: $6748 (4 )

Serene Sunrise & Shimmering Skyline. 5 Star Hosts

4 2
apartment , Ocean City
This West Ocean City waterfront property, a luxurious four-bedroom house, is situated 6.8km from the Ocean City Boardwalk, offering easy access to the beach and amusement parks.
Sleeping up to ten guests, this spacious holiday home boasts four king-size beds, a private hot tub, bonfire pit, canal access (by prior arrangement), and kayaks and beach equipment for guest use.
Newley Renovated Beach Home, Min. To Ocean City,1st Fl. Master Suite, Walk In - Ocean Pines, MD
10 23 reviews
Ocean Pines, MD
27/06 – 01/07
$572/nighttotal: $2288 (4 )

Newley Renovated Beach Home, Min. To Ocean City,1st Fl. Master Suite, Walk In

3 4
apartment , Ocean Pines
This Ocean Pines holiday home is situated 0.5km from Isle of Wight Bay, offering easy access to boating and fishing, and within 5km of Manklin Meadows Racquet Centre and Ocean Pines Golf and Country Club.
The three-bedroom property, sleeping eight guests, boasts a private indoor pool, a fully equipped kitchen, and a peaceful garden, alongside a jacuzzi and outdoor terrace; River Run Golf Club and Casino at Ocean Downs are also within a short drive (10km).
Wight Bay 443 By Seaside Vacations & Sales - Ocean Pines, MD
9.6 9 reviews
Ocean Pines, MD
05/09 – 12/09
$429/nighttotal: $3003 (7 )

Wight Bay 443 By Seaside Vacations & Sales

2 2
apartment , Ocean City
Wight Bay 443, a two-bedroom apartment in Ocean City's midtown on 47th Street, offers easy access to the beach, and is a short drive (approximately 1.6 to 3.2 km) from both the Ocean City Boardwalk and West Ocean City's restaurants.
This self-catering holiday flat sleeps six guests, boasting a well-equipped kitchen, private balcony with bay views, en-suite bathrooms (one with a walk-in shower, the other with a shower/bath), in-unit laundry, and access to a seasonal outdoor swimming pool.
©2026 cozycozy.com