Ocean Pines vacation rentals

We found 7,218 vacation rentals — enter your dates for availability

Discover a selection of 116 homes and other vacation rentals in Ocean Pines that are perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll have the amenities you expect and more, which might include parking and a pool. Whatever you're looking for, you're sure to find a rental for everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Ocean Pines

Showing deals for:Jun 19 - Jun 26

Image gallery for Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in

Interior
10 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)

Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in

Berlin

8% off
Price is $416
$2,914 for 7 nights
All fees included
Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in

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Find out more about Ocean Pines

Why visit Ocean Pines

  • Beautiful Beaches: Enjoy pristine sandy shores and collect unique coral shells along the coast.
  • Outdoor Adventures: Engage in various activities like hiking and exploring scenic areas, including nearby marinas.
  • Family-Friendly Attractions: Visit local amusement parks and vibrant Ocean City for fun experiences.
  • Charming Neighborhoods: Discover friendly communities rich in history and culture.
  • Variety of Accommodations: Choose from cozy condos to spacious vacation homes with pool access.

Popular types of accommodation around Ocean Pines

Explore a variety of vacation rentals in Ocean Pines, Maryland, perfect for your getaway. Whether you prefer a private vacation home, a cozy condo, or a spacious apartment, you'll find the ideal accommodation to suit your needs. With options that often include pools and easy access to local attractions, your Ocean Pines experience promises relaxation and fun. Discover your perfect MD vacation rental today.

  • Houses: The top choice for visitors in Ocean Pines, offering spacious accommodations ideal for families or groups.
  • Condos: A popular option for those seeking modern amenities and a community feel during their stay.
  • Apartments: A convenient selection for travelers looking for a home-like atmosphere with easy access to local attractions.
  • Cottages: These quaint and cozy rentals provide a charming escape for a relaxing vacation.
  • Villas: Upscale and luxurious, perfect for those wanting a more indulgent experience.**

Top attractions near Ocean Pines

Ocean Pines, Maryland, is the perfect destination for outdoor and romantic beach vacations. Visitors can explore beautiful beaches, enjoy the local esplanade, and have fun at nearby amusement parks. The area offers a variety of attractions for families and culture enthusiasts alike, with opportunities to access marinas, discover orange beach and Gulf Shores, and explore the scenic beauty of Hocking Hills. Don’t miss the chance to collect unique coral shells during your trip.

  • Ocean City Boardwalk: A lively esplanade filled with shops, restaurants, and entertainment. Perfect for families and couples, the boardwalk offers stunning ocean views and a vibrant atmosphere, making it ideal for leisurely strolls and memorable moments.
  • Ocean City Beach: A picturesque beach renowned for its soft sand and inviting waters. This beach is perfect for sunbathing, swimming, and enjoying beach vibes, providing a relaxing escape for visitors of all ages.
  • Jolly Roger Amusement Park: An exciting amusement park offering thrilling rides and family-friendly attractions. With a blend of adventure and outdoor fun, it’s a great place for creating lasting memories with loved ones.

Things to do recommended for couples

For a romantic getaway in Ocean Pines, explore the serene beauty of Assateague Island, just a short drive away. Enjoy a sunset dinner at a waterfront restaurant, or take a leisurely stroll along the beach, hand in hand, as the waves gently lap at your feet.

Things to do recommended for families

Families visiting Ocean Pines can enjoy a day at the nearby Assateague Island National Seashore, where kids can see wild ponies and play on beautiful beaches. Additionally, the Jolly Roger Amusement Park in Ocean City offers thrilling rides and games for a fun-filled day.

Things to do recommended for groups

Groups visiting Ocean Pines can enjoy a relaxing day at the beach, explore the scenic hiking trails in nearby Assateague Island National Seashore, or partake in fun water sports at the local marina. Don't miss out on the vibrant dining scene and local shops in Berlin.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Ocean Pines

When planning your trip—whether you're with a group, traveling as a family, bringing your pets, or seeking extended stays—be sure to filter your options based on your top priorities. Here are some helpful tips for booking on Vrbo.

  • Traveling to Ocean Pines with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Ocean Pines with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Ocean Pines: For many families, a vacation isn't truly enjoyable without their furry companions by their side. If you can relate, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Ocean Pines: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Ocean Pines

Ocean Pines, Maryland, offers a delightful blend of outdoor adventures and relaxing beach vibes, making it an ideal destination for romantic getaways or family vacations. Explore the nearby oceanfront areas and the vibrant atmosphere of Ocean City, MD, where fun and recreation await. Discover the charm of local neighborhoods with friendly people and rich history, ensuring a memorable experience filled with scenic beauty and relaxation.

  • Ocean City: Located 6 miles from Ocean Pines, Ocean City is a vibrant coastal city known for its dynamic boardwalk, stretching over 3 miles along the beach. Here, families and couples alike can enjoy various outdoor activities, including sunbathing, beach volleyball, and watersports. The area is also home to an array of shops, restaurants, and amusement parks, making it a perfect destination for those seeking fun and adventure. Key landmarks such as the Esplanade and family-friendly beaches provide a picturesque backdrop for unforgettable vacation memories.
  • Isle of Wight: Situated 3 miles from Ocean Pines, Isle of Wight is a charming island that offers a serene escape into nature. This destination is ideal for outdoor enthusiasts and families, with scenic views and activities like golfing and exploring the local marina. Visitors can enjoy leisurely walks along the boardwalk or catch a show at the local theater. The scenic bay and Esplanade are perfect for picturesque picnics and sunset views, making Isle of Wight a delightful spot for a romantic getaway or family outing.
  • North Ocean City: Also located 6 miles from Ocean Pines, North Ocean City is a laid-back neighborhood that boasts beautiful beaches and outdoor recreation. Known for its welcoming atmosphere, this area features a lively boardwalk, shopping zones, and recreation parks that cater to all ages. Visitors can spend the day on the sandy shores or enjoy a leisurely stroll along the Esplanade. North Ocean City is perfect for those looking to combine beach relaxation with fun activities, making it an attractive choice for both romantic escapes and family vacations.

Best time to go to Ocean Pines

If you're planning a trip to Ocean Pines, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January38.1°F (3.4°C)Light RainMostly SunnyAverageSlightly Low
February40.1°F (4.5°C)Light RainMostly SunnyAverageSlightly Low
March45.3°F (7.4°C)Light RainMostly SunnyAverageSlightly Low
April54.5°F (12.5°C)Light RainMostly SunnyAverageAverage
May63.1°F (17.3°C)Light RainMostly SunnyAverageAverage
June72.0°F (22.2°C)Light RainMostly SunnyHighSlightly High
July77.5°F (25.3°C)Light RainMostly SunnyHighSlightly High
August76.3°F (24.6°C)Light RainMostly SunnyHighSlightly High
September71.2°F (21.8°C)Light RainMostly SunnyAverageAverage
October62.1°F (16.7°C)Light RainMostly SunnyLowAverage
November50.9°F (10.5°C)Light RainMostly SunnyLowAverage
December44.1°F (6.7°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire booking. Being the planner definitely has its perks. When you join our travel rewards program, One Key, you’ll gain access to exclusive discounts and earn OneKeyCash on eligible reservations. Sign up today and start enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's groundbreaking Trip Board offers you a dedicated area to plan new trips, pick up from where you last stopped, or review and arrange your travel plans. You can easily access properties you've saved or booked in sections like Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Ocean Pines?
In Ocean Pines, vacation houses are the most prevalent rental option, with about 174 available throughout the community. These properties typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking for comfort and convenience. Many houses also include outdoor spaces such as decks or patios, superb for enjoying the pleasant Maryland weather. Additionally, there are around 20 cottages, which offer a charming, cozy alternative for those seeking a more intimate stay.
Are there any beach house rentals in Ocean Pines?
In Ocean Pines, there are approximately 263 beach house vacation rentals available, making it a popular destination for travelers. These rentals are primarily located in peaceful neighborhoods, providing a relaxing atmosphere away from the hustle and bustle. Travelers can expect a variety of amenities, including fully equipped kitchens for home cooking, spacious living areas for gathering, and outdoor decks or patios for enjoying the pleasant coastal climate. Many properties also feature multiple bedrooms, which are ideal for families or larger groups.
How much does it cost to rent a vacation home in Ocean Pines?
Prices for vacation rentals in Ocean Pines vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Ocean Pines to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Ocean Pines vacation house rentals?
You can find great discounts on house rentals in Ocean Pines on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Ocean Pines?
In Ocean Pines, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals conveniently. Many rentals also feature coffee and tea makers, ideal for those who enjoy a warm beverage in the morning. Onsite parking is a common amenity, providing easy access for travelers with vehicles. Additionally, many properties offer outdoor spaces such as decks or patios, superb for relaxing and enjoying the pleasant Maryland weather.
Can I find family house rentals in Ocean Pines?
In Ocean Pines, Maryland, there are numerous family-friendly house rentals available—specifically around 137 options to choose from. This community is well-suited for families, with spacious homes that often include multiple bedrooms, inviting living areas, and outdoor spaces for kids to enjoy. Many properties come equipped with full kitchens, allowing families to prepare meals together, as well as amenities such as Wi-Fi and air conditioning for added comfort.

The location is ideal for families looking to explore nearby attractions. Visitors can easily access the beaches of Ocean City, just a short drive away, where fun in the sun awaits. Additionally, the community has its own amenities, including parks, pools, and recreational facilities, ensuring that there's plenty to do right at your doorstep.
Can I rent a vacation home with a pool or hot tub in Ocean Pines?
In Ocean Pines, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 152 options for properties with pools and 13 that include hot tubs. This charming coastal community offers a variety of neighborhoods where these rentals can be found, including the serene areas near the marina and the more vibrant sections close to local amenities and recreational facilities.

Travelers can expect a range of amenities in these vacation homes, including private pools, relaxing hot tubs, spacious outdoor areas for gatherings, and fully equipped kitchens ideal for preparing meals. Many properties also have features such as outdoor dining spaces, barbecue grills, and easy access to nearby beaches, enhancing the overall enjoyment of a getaway in this picturesque setting.
Are there any Ocean Pines vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Ocean Pines with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I book pet-friendly vacation rentals in Ocean Pines?
Yes, you can book pet-friendly vacation rentals in Ocean Pines, where there are approximately 72 options available to choose from. This community, located near the scenic shores of the Atlantic Ocean, offers a variety of properties that cater to travelers with pets. Many of these rentals come equipped with amenities such as spacious backyards, outdoor decks, and fully stocked kitchens, providing a comfortable home base for your stay.

In addition to the vacation rentals, Ocean Pines is conveniently located near several pet-friendly points of interest. The nearby beaches, particularly in the Ocean City area, welcome pets during certain times of the year, allowing for enjoyable beach outings. Additionally, the community features parks and walking trails that are great for daily strolls with your furry companions.
Can I find long-stay vacation rentals in Ocean Pines?
A long-stay vacation rental in Ocean Pines is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Ocean Pines for a vacation rental?
July is the most popular time to visit Ocean Pines, as families and beach enthusiasts flock to the area for sun-soaked days and a vibrant setting. The peak season extends from June to August, characterized by a lively blend of outdoor activities, including water sports, beach outings, and local festivals. Visitors can expect warm temperatures, typically ranging from the mid-70s to low 90s Fahrenheit, great for enjoying the beautiful coastal scenery and the nearby beaches.

During these summer months, Ocean Pines offers an array of activities, from kayaking in the tranquil waters to exploring the local nature trails. The community buzzes with energy, making it an ideal time for those seeking camaraderie and dynamic experiences.

For travelers looking for a more budget-friendly option, consider visiting in November. This month provides a quieter atmosphere while still allowing for enjoyable walks along the beach and the opportunity to appreciate the region's natural beauty without the summer crowds.

Ultimately, the best time for you to book a vacation rental in Ocean Pines depends on your preference for lively summer adventures or a more peaceful retreat in the off-season.
Are there any remote work vacation rentals in Ocean Pines?
In Ocean Pines, Maryland, travelers will find a substantial selection of remote work-friendly vacation rentals, with around 181 options available. This community offers a tranquil environment along the picturesque coastal region, making it an attractive choice for those looking to balance work and leisure. Many of the rentals come equipped with essential amenities such as high-speed Wi-Fi and dedicated workspaces, ensuring a productive atmosphere.

The area is known for its proximity to various recreational activities, including boating, fishing, and beautiful beaches. Rentals often feature comfortable living areas, full kitchens for meal preparation, and outdoor spaces ideal for relaxation or taking breaks during the workday. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Ocean Pines vacation rental?
Book your Ocean Pines vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Ocean Pines, Maryland, United States of America?
In Ocean Pines, visitors can enjoy a range of attractions that highlight the area's natural beauty and recreational opportunities. The community is known for its picturesque waterfront views and access to several lakes, making it ideal for fishing, kayaking, and paddleboarding. The nearby Ocean Pines Golf Club offers a well-maintained course for golf enthusiasts, while the community center hosts various events and activities throughout the year.

For those looking to relax, the nearby beaches, such as Ocean City, are just a short drive away, providing opportunities for sunbathing, swimming, and beachside dining. The area also features several parks and nature trails, superb for walking, biking, or simply enjoying the outdoors.
Can I change or cancel my Ocean Pines home rental booking on Vrbo?
To find Ocean Pines vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Ocean Pines vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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