Compare best Airbnb in Ocean Pines, MD from 100+ providers!
481 available vacation rental offers
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating
Best Vacation rentals and Airbnb offers in Ocean Pines, MD
9.9 77 reviews
Ocean Pines, MD
09/05 – 09/12
$267/nighttotal: $1869 (7 )
Cozy Home In Ocean Pines
1 2
apartment , Ocean Pines
This Ocean Pines yacht rental is conveniently located 7.4 miles from Ocean City, 13 miles from Assateague Island, and 7 miles from Berlin, offering easy access to beaches, golf courses, and community amenities. The three-bedroom, two-bathroom houseboat sleeps six guests and features a fully equipped kitchen, swimming pool, and outdoor spaces including a deck, grill, and fire pit, plus beach essentials are provided.
Ocean Pines, MD
07/13 – 07/17
$376/nighttotal: $1504 (4 )
4th Floor Glow | Bay Views That Steal The Show
1 2
apartment , Ocean City
This fourth-floor bayfront condo is situated two blocks from the Ocean City Trolley and five blocks from the Boardwalk, offering ocean proximity without overwhelming noise. This two-bedroom, two-bathroom unit sleeps up to six guests, features balcony access, a fully stocked kitchen, WiFi, an in-unit washer/dryer, and access to resort amenities including an indoor pool and hot tub, with pets allowed for an additional fee.
9.6 37 reviews
Ocean Pines, MD
07/13 – 07/17
$323/nighttotal: $1292 (4 )
Beachside Luxury Top-floor Studio -Two Blocks From The Waves. Linens Included!!
1 2
studio , Ocean City
This Midtown Ocean City rental is a 5-minute walk from Isle of Wight Bay and Jolly Roger Amusement Park, and a 15-minute walk from Ocean City Beach and the Boardwalk. This 380-square-foot apartment sleeps three guests and features a full kitchen, private balcony, free WiFi, and access to onsite amenities including sun loungers, beach towels, and parking.
10 1 review
Ocean Pines, MD
06/20 – 06/27
$527/nighttotal: $3689 (7 )
Broadmarsh 115c
4 6
apartment , Ocean City
This midtown Ocean City townhome is located just 0.2 miles from the beach and offers convenient access to dining and amusements. This 4-bedroom, 3.5-bathroom townhome accommodates up to 10 guests with a fully equipped kitchen, central air conditioning, and access to a seasonal community pool.
10 18 reviews
Ocean Pines, MD
07/13 – 07/17
$324/nighttotal: $1296 (4 )
Stubbe's Beach House,
Home In Ocean Pines, Md
1 2
apartment , Ocean Pines
This waterfront condo in Ocean Pines is located in the gated White Horse Park community, offering a private dock and convenient access to Ocean City, Assateague Island National Seashore, and downtown Berlin. This 2-bedroom, 1-bathroom rental accommodates up to 4 guests and features a fully stocked kitchen, air conditioning, a swimming pool, and adult-size bikes for exploring the community.
9.8 131 reviews
Ocean Pines, MD
07/18 – 07/25
$523/nighttotal: $3661 (7 )
Bright Midtown Condo With Pool/hot Tub Restaurants, Family Spots, And The Beach!
2 6
apartment , Ocean City
This Ocean City apartment is conveniently located in Midtown, a short walk from both the beach and the bay, and just a short drive from the famous Ocean City Boardwalk. The apartment has received excellent ratings for location, cleanliness, and overall experience. The two-bedroom apartment, spanning 1050 square feet, comfortably accommodates up to seven guests. Enjoy a range of amenities including a pool, jacuzzi, sauna, fitness center, and a fully equipped kitchen.
9.8 97 reviews
Ocean Pines, MD
07/18 – 07/25
$366/nighttotal: $2562 (7 )
2 Mi To Golf: Hot Tub Hideaway In Ocean Pines
3 6
house , Ocean Pines
This Ocean Pines house is located just 2 miles from the golf course and a short drive from popular attractions like Grand Prix Amusements and Baja Amusements, offering a peaceful retreat while being close to entertainment options. It has received excellent ratings for user experience, location, and cleanliness. The 2010 square foot home offers 3 bedrooms and 2 bathrooms, comfortably accommodating up to 6 guests. You'll enjoy a private hot tub, a fully equipped kitchen, free Wi-Fi, air conditioning, a swimming pool, a jacuzzi, a garden, a spa, a fitness center, a tennis court, and parking.
8.0 6 reviews
Ocean Pines, MD
07/22 – 07/29
$317/nighttotal: $2219 (7 )
9 Mi To Beach! Family Getaway In Ocean Pines
2 2
house , Ocean Pines
This Ocean Pines vacation home is located 9 miles from Ocean City beaches and within 7 miles of Grand Prix Amusements and Baja Amusements. The 860-square-foot property features two bedrooms, one bathroom, and can comfortably accommodate seven guests, boasting a fully equipped kitchen, swimming pool, and free Wi-Fi.
Ocean Pines, MD
06/20 – 06/27
$445/nighttotal: $3115 (7 )
Bayside 2-bedroom Condo With Pool Access, Bright Living Space, And Relaxing Coastal Vibes.
2 6
apartment , Ocean City
This bayside condo rental in North Ocean City, Maryland, near 123rd Street, offers easy walking access to Northside Park and is just a short distance from Ocean City Beach. This 1163 square foot unit features two bedrooms, three bathrooms, sleeps eight guests, and includes a fully equipped kitchen, in-unit laundry, two private balconies, access to a community pool, and is close to Jolly Roger Amusement Park and other attractions.
Ocean Pines, MD
07/22 – 07/29
$486/nighttotal: $3402 (7 )
3br/2ba Ocean Pines Home W/ Screened Porch & Deck Near Pools, Golf & Yacht Club! New Listing!
3 2
apartment , Ocean Pines
This Ocean Pines condo is located near Ocean City beaches and the Ocean Pines Yacht Club, offering wooded views and convenient access to community pools, nature trails, and Assateague Island's wild horses. This 3-bedroom, 2-bathroom rental spans 13260 square feet and accommodates up to 5 guests, featuring a private deck, screened porch, fully equipped kitchen, and air conditioning, with parking and internet provided.
10 63 reviews
Ocean Pines, MD
09/05 – 09/12
$334/nighttotal: $2338 (7 )
Cozy Home 8 Miles From Ocmd *Beach Pass Included*
1 2
apartment , Ocean Pines
This Ocean Pines vacation home is minutes from Ocean City and its beach, offering easy access to the Ocean Pines Beach Club on 49th Street. The recently renovated three-bedroom, two-bathroom house sleeps six, features a screened-in porch with a grill and fire pit, smart TVs, a full kitchen with dishwasher, and a Jacuzzi, plus provides linens, towels and beach parking pass.
8.0 1 review
Ocean Pines, MD
06/20 – 06/27
$409/nighttotal: $2863 (7 )
3 Bedroom 2 Bath House Featuring Wifi Smart Tv Huge Deck And Patio Beach Parking
3 6
apartment , Ocean Pines
This Ocean Pines vacation home, located in Berlin, Maryland, offers easy access to Ocean City Beach and attractions like Jolly Roger and Frontier Town amusement parks. The 3-bedroom, 2-bathroom house sleeps eight guests and features a fully equipped kitchen, a large deck with a grill, central air conditioning, Wi-Fi, and a nearby pool (fee applies).
Best Ocean Pines, MD vacation rentals with a balcony
9.8 8 reviews
Ocean Pines, MD
06/20 – 06/27
$374/nighttotal: $2618 (7 )
17th Floor = Incredible Ocean And Bayviews. Lovely Condo, Well Furnished. Many Amenities.
2 6
apartment , Ocean City
This Ocean City condo is located in North Ocean City, a short walk from the beach, Gold Coast Mall, and other attractions. It has received excellent user ratings, making it a popular choice for travelers. The apartment has two bedrooms and two bathrooms, perfect for a family or group of friends. You'll enjoy access to a swimming pool, fitness center, tennis court, and other amenities, plus a balcony for enjoying the fresh air and Ocean City views.
10 6 reviews
Ocean Pines, MD
06/20 – 06/27
$379/nighttotal: $2653 (7 )
** Select 2023 Weeks Have Been Discounted By $200.00! Prices Shown Include Discount. **<Br>2 Br/2 Bath Antigua / Outdoor Pool/ofront Bldg, Back Unit
2 6
apartment , Ocean City
This North Ocean City condo offers bay views from a private balcony and is located within a short distance of Ocean City Beach and Jolly Roger Amusement Park. This 2-bedroom, 2-bathroom condo sleeps 6 and features a newly remodeled interior with quartz countertops, stainless steel appliances, a dishwasher, free WiFi, three Smart TVs, and an in-unit washer/dryer, with access to a heated outdoor pool and complimentary cleaning.
Ocean Pines, MD
07/18 – 07/25
$659/nighttotal: $4613 (7 )
Lighthouse Cottage | Ocean Pines, Golf & Oc Beach
4 6
apartment , Ocean Pines
This coastal cottage is located in the Huntington section of Ocean Pines, a peaceful neighborhood just a short drive from the Ocean City, Maryland beaches and boardwalk. This 1800 square foot residence accommodates up to 8 guests with 4 bedrooms, 2 bathrooms, a full kitchen, and a screened porch, offering convenient access to Ocean Pines amenities and nearby attractions like Assateague Island.
Search Family Vacation Rentals in Ocean Pines, MD
Perfect for family trips, these spacious Ocean Pines, MD rentals and Airbnbs provide easy access to local beaches.
9.8 17 reviews
Ocean Pines, MD
07/18 – 07/25
$331/nighttotal: $2317 (7 )
Lovely Mallard Lakes Townhome, Minutes From Fenwick And Oc Beaches.
2 6
apartment , Fenwick Is
This Selbyville townhome, located two miles from Ocean City Beach and Maryland Beach, offers convenient access to Fenwick Island's attractions. The two-bedroom, two-bathroom property sleeps six guests comfortably and boasts a fully equipped kitchen, a sunroom overlooking the lake, Roku TVs, a private patio, community pools, and tennis/pickleball courts.
10 6 reviews
Ocean Pines, MD
07/18 – 07/25
$380/nighttotal: $2660 (7 )
Cabin In The Pines I Luxury Touches + Ev Charging
1 6
apartment , Ocean Pines
This secluded coastal condo in Ocean Pines offers a family-friendly stay, located just minutes from Ocean City's beaches, dining, and entertainment. This 3-bedroom, 2-bathroom rental accommodates up to 8 guests and features a fully equipped kitchen, spa-like bathrooms, an office area, a surround-sound system, and a fenced yard with EV charging, plus access to 5 community pools at resident rates.
9.7 135 reviews
Ocean Pines, MD
07/18 – 07/25
$610/nighttotal: $4270 (7 )
Gated Renovated 2 Level Condo Downtown Oc Bayview
2 6
apartment , Ocean City
This Ocean City condo is located in the downtown area, steps from the beach and boardwalk, and within a five-minute walk of attractions like Jolly Roger at the Pier and Ripley's Believe It or Not!. This 1020-square-foot, two-bedroom, two-bathroom unit sleeps seven and features a fully equipped kitchen, private balcony, free WiFi, and access to a swimming pool and water park.
Frequently Asked Questions about vacation rentals in Ocean Pines, MD
What sports or outdoor activites can visitors enjoy in and around Ocean Pines, MD?
Ocean Pines is a haven for water sports enthusiasts. You can enjoy swimming, fishing, boating, kayaking, and paddleboarding in the bay. If you're feeling adventurous, try surfing or kiteboarding on the Atlantic Ocean. For a more relaxed experience, try a round of golf at the Ocean Pines Golf Course.
What are the best Airbnb and vacation rentals 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 offers a lively boardwalk, amusement parks, and plenty of restaurants and shops. If you're looking for a more laid-back atmosphere, visit the historic town of Berlin, known for its charming shops and restaurants. For a taste of nature, head to Assateague Island, home to wild horses and beautiful beaches.
What are the most popular Airbnbs in Ocean Pines, MD?
What amenities are commonly available in vacation rentals in Ocean Pines, MD?
Vacation rentals in Ocean Pines typically offer a range of amenities, including private decks or balconies, swimming pools, hot tubs, and fully equipped kitchens. Many also have access to community amenities such as tennis courts, playgrounds, and fitness centers.
What are the best vacation rentals with a pool in Ocean Pines, MD?
What time of year is best to rent a vacation rental Ocean Pines, MD?
Summer is the most popular time to visit Ocean Pines, but the shoulder seasons, spring and fall, offer milder temperatures and fewer crowds. If you're looking for a more affordable option, consider visiting during the off-season, from November to April.
What are the best rentals for families and kids in Ocean Pines, MD?
What are the local dishes in Ocean Pines, MD region?
Being on the coast, seafood is a local favorite. Try fresh oysters, crabs, and fish, often prepared with a Maryland-style seasoning. For a taste of the region, look for dishes like crab cakes, seafood bisque, and steamed crabs. You'll find many restaurants serving these local specialties in Ocean Pines and the surrounding areas.
What are the best rentals or Airbnbs with a jacuzzi in Ocean Pines, MD?
Best Ocean Pines, MD vacation rentals with parking
9.8 77 reviews
Ocean Pines, MD
07/18 – 07/25
$545/nighttotal: $3815 (7 )
Charming 2br 2ba Direct Bayfront Unit. Enjoy The Best Fishing & Sunsets Here.
2 6
apartment , Ocean City
This updated 2-bedroom, 2-bathroom condo in Downtown Ocean City is located at 6th Street, just a short walk from the boardwalk and numerous restaurants, offering spectacular bay views and a prime fishing location with piers dropping to 45 feet. This ocean city rental accommodates up to 6 guests and features a full kitchen with modern appliances, complimentary Wi-Fi, air conditioning, a washer/dryer, and a balcony perfect for enjoying East Coast sunsets.
10 23 reviews
Ocean Pines, MD
06/20 – 06/27
$430/nighttotal: $3010 (7 )
Newley Renovated Beach Home, Min. To Ocean City,1st Fl. Master Suite, Walk In
3 6
apartment , Ocean Pines
This Ocean Pines vacation home is situated 0.3 miles from Isle of Wight Bay, within 3 miles of Manklin Meadows Racquet Center and Ocean Pines Golf and Country Club, and conveniently close to River Run Golf Club and Casino at Ocean Downs (6 miles away). This 3-bedroom, 3-bathroom house sleeps 8 guests, boasting a private indoor pool, outdoor swimming pool, jacuzzi, and a fully equipped kitchen including a refrigerator, microwave, and dishwasher; enjoy free WiFi, a relaxing garden, and proximity to various Ocean Pines attractions.
Ocean Pines, MD
07/13 – 07/17
$395/nighttotal: $1580 (4 )
House ∙ 2 Bedrooms ∙ 4 Guests
2 2
house , Ocean Pines
This bayside home in Ocean Pines is a short drive from Ocean City, Assateague Island, and Berlin, offering a quiet coastal escape with access to nearby fishing areas and a boat ramp. This pet-friendly rental accommodates up to four guests in two bedrooms and features a well-equipped kitchen, complimentary Wi-Fi, central air conditioning, and access to an outdoor community pool and kayaks.
This Ocean City condo offers an ocean block location, just steps from the beach and boardwalk in Midtown, with Seacrets and Midway Shopping Center nearby. This 650 sq ft unit accommodates up to 4 guests, featuring a full kitchen, air conditioning, a private balcony with a partial ocean view, in-unit laundry, dedicated parking, and complimentary beach gear.
Check Out Vacation Rentals with a Pool in Ocean Pines, MD
A vacation rental with a pool in Ocean Pines, MD is the ideal way to complement your daily coastal adventures.
9.5 157 reviews
Ocean Pines, MD
06/20 – 06/27
$188/nighttotal: $1316 (7 )
Bayside - Summer Winds Complex - 2 Bedroom, Pool
2 6
apartment , Ocean City
This Summer Winds apartment rental near 28th Street in Ocean City, Maryland, is conveniently located four blocks from the beach and boardwalk. The two-bedroom, one-bathroom condo sleeps six, features a fully equipped kitchen, in-unit laundry, and access to a swimming pool and parking.
9.0 25 reviews
Ocean Pines, MD
07/13 – 07/17
$288/nighttotal: $1152 (4 )
Makai Is Conveniently Located On 42nd Street And The Bayfront
1 2
apartment , Ocean City
This centrally located apartment in Midtown Ocean City is a 10-minute walk from the beach and the Isle of Wight Bay. With an excellent user rating, this apartment features a private balcony, a fitness center, and an indoor pool. The apartment has one bedroom, one bathroom, air conditioning, a fully equipped kitchen with a dishwasher and a microwave, a seating area with a sofa, and a flat-screen TV with a DVD player. In-unit laundry facilities, free parking, and a smoke-free environment are also available.
9.0 42 reviews
Ocean Pines, MD
07/13 – 07/17
$292/nighttotal: $1168 (4 )
Modern Efficiency Unit Located On 42nd Street, Close To Beach And Convention Center!
1 2
apartment , Ocean City
This Ocean City rental is conveniently located in Midtown, just a 5-minute walk from the bay and the convention center, with the beach and boardwalk within a mile. Guests have consistently rated this property as excellent, highlighting its prime location and comfortable amenities. The apartment features a balcony for enjoying the fresh air, a TV with a DVD player for relaxing evenings, and a washing machine and microwave for added convenience. You'll also have access to a swimming pool, fitness center, and parking, making this a great choice for families and groups looking for a comfortable and enjoyable stay.
Ocean Pines, MD
07/18 – 07/25
$297/nighttotal: $2079 (7 )
Charming Ocean Pines Retreat With Porch!
3 6
apartment , Ocean Pines
This 3-bedroom, 2-bathroom condo in Ocean Pines, MD, is located within 2 miles of Ocean City beaches and boardwalk, and offers easy access to Ocean Pines amenities including community pools, golf courses, and the Yacht Club. This rental accommodates up to 7 guests and features a fully equipped kitchen, air conditioning, and a screened-in porch, with nearby opportunities for bay boating, fishing, kayaking, and biking.
Find the Best Seaside Vacation Rentals in Ocean Pines, MD
Discover charming seaside vacation rentals in Ocean Pines, MD near the coast. Browse our favorite coastal picks to find your perfect beach-town match.
9.2 3 reviews
Ocean Pines, MD
06/20 – 06/27
$346/nighttotal: $2422 (7 )
Atlantic View 101 Condo
2 6
apartment , Ocean City
8.0 1 review
Ocean Pines, MD
06/20 – 06/27
$338/nighttotal: $2366 (7 )
One Of Ocean City's Premiere Condos
1 6
apartment , Ocean City
9.8 46 reviews
Ocean Pines, MD
06/20 – 06/27
$573/nighttotal: $4011 (7 )
You Are Going To Love The Ocean Views From The Huge Ocean Front Balcony!
2 6
apartment , Ocean City
Ocean Pines, MD
06/20 – 06/27
$254/nighttotal: $1778 (7 )
Cute, Cozy One Bedroom, One Bath Condo With An Oceanfront Balcony, So Come And Enjoy Beautiful Ocean Views!
1 6
apartment , Ocean City
Compare Luxury Vacation Rentals in Ocean Pines, MD
Discover the best of the coast with a luxury vacation rental in Ocean Pines, MD, offering sophisticated rooms and prime locations.
10 12 reviews
Ocean Pines, MD
07/22 – 07/29
$589/nighttotal: $4123 (7 )
Downtown Condo, Parking, Walk To Beach & Boardwalk
1 2
apartment , Ocean City
Discover Vacation Rentals with Saunas in Ocean Pines, MD
Maximize your recovery with an on-site sauna, a standard feature at these premier Ocean Pines, MD vacation rentals.
Ocean Pines, MD
07/13 – 07/17
$218/nighttotal: $872 (4 )
Bay-view Makai Studio With Shared Pool, Gym, Sauna, & Billiards - Walk To Beach
1 2
studio , Ocean City
Ocean Pines, MD
07/22 – 07/29
$618/nighttotal: $4326 (7 )
Uptown Oc 2 Bedroom | Pool, Sauna & Pickleball
2 2
apartment , Ocean City
8.2 18 reviews
Ocean Pines, MD
07/22 – 07/29
$707/nighttotal: $4949 (7 )
Ocean-view Condo With Balcony, W/d, Pools, Saunas, Tennis & Gym
2 2
apartment , Ocean City
Ocean Pines, MD
09/05 – 09/12
$288/nighttotal: $2016 (7 )
Golden Sands 1106: Gorgeous Oceanfront 1br Condo | Fully Renovated And Decorated
