Ocean Pines vacation rentals

We found 7,497 vacation rentals — enter your dates for availability

Select from 213 homes, 23 cottages, and other vacation rentals in Ocean Pines to find one that's 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:Nov 7 - Nov 14
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Find out more about Ocean Pines

Find out more about Ocean Pines

Why visit Ocean Pines

  1. Stunning Beaches: Ocean Pines boasts beautiful sandy beaches perfect for sunbathing and swimming.
  2. Outdoor Adventures: Ideal for nature lovers, offering hiking, biking, and water sports.
  3. Family-Friendly Activities: Explore amusement parks and various attractions suitable for all ages.
  4. Charming Atmosphere: Enjoy the welcoming vibe of the Whimsy Waterfront and friendly locals.
  5. Diverse Accommodation: Choose from cozy condos to spacious vacation homes for a perfect stay.

Popular types of accommodation around Ocean Pines

Planning a getaway to Ocean Pines? You're in for a treat! Discover the ideal accommodation options, from cozy condos to spacious houses and stylish apartments. Whether you're seeking a relaxing retreat or an adventure-filled holiday, our vacation rentals offer the perfect base for your Ocean City MD experience. Explore the variety of sea pines vacation rentals available and enjoy your stay with transparency, savings, and peace of mind.

  • Condos: Condos are the top choice for vacation rentals in Ocean Pines, offering modern amenities and convenient locations.
  • Houses: These spacious homes provide a perfect retreat for families or groups, ensuring privacy and comfort.
  • Apartments: Ideal for solo travellers or couples, apartments are a popular option for a home-like stay.
  • Cottages: Quaint and charming, cottages offer a cozy atmosphere for a relaxing getaway.
  • Villas: Luxurious and spacious, villas are perfect for those seeking an upscale vacation experience.**

Top attractions around Ocean Pines

Ocean Pines, Maryland, offers a delightful getaway for outdoor enthusiasts, couples, and beach lovers alike. Visitors can enjoy stunning beaches, lovely esplanades, and thrilling amusement parks. The area is perfect for families seeking cultural experiences and outdoor adventures, making it an ideal destination for a memorable vacation. Whether you're exploring with loved ones or enjoying some quiet time, Ocean Pines has something special for everyone.

  1. Ocean City Boardwalk: A lively esplanade perfect for families and couples, offering a delightful mix of shops, restaurants, and entertainment along the picturesque coastline.
  2. Ocean City Beach: A beautiful stretch of sandy shore where you can relax, swim, and soak up the sun, embodying the quintessential beach vibe.
  3. Jolly Roger Amusement Park: An exciting amusement park filled with thrilling rides and attractions, ideal for family adventures and outdoor fun.

Things to do recommended for couples

Ready for a romantic getaway in Ocean Pines? Enjoy a fun round at Maui Golf, sip exquisite wines at Costa Ventosa Vineyard and Winery, or embark on an adventurous outing with water sports at Shark's Cove Marina. Each experience is perfect for couples seeking memorable moments together.

Things to do recommended for families

Your family will love Northside Park for its relaxing atmosphere, the Carousel Ice Skating Rink for thrilling ice skating fun, and Frontier Town Water Park and Golf for a day filled with water adventures and entertainment, all just a short drive from Ocean Pines.

Things to do recommended for groups

Groups visiting Ocean Pines can enjoy a thrilling night at the Casino at Ocean Downs, indulge in craft spirits at Seacrets Distilling Company, or hit the greens at the Bayside Resort Golf Club for some outdoor fun and camaraderie.

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

If you're travelling with a group, family, or pets, or if you're considering a longer stay, be sure to use the appropriate filters to match your needs. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Ocean Pines with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor space for group gatherings. The good news is that you can easily filter for these options and much more on Vrbo.
  • Traveling to Ocean Pines with young kids: Traveling with young children can present some challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Ocean Pines: For many families, a vacation wouldn’t feel complete without their furry companion. If this resonates with you, consider exploring Vrbo properties that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Ocean Pines: If you’re seeking vacation rentals with 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 amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay around Ocean Pines

Ocean Pines, Maryland, is a delightful destination for outdoor enthusiasts and couples seeking a romantic beach escape. Just a stone's throw from the vibrant Ocean City, visitors can enjoy stunning ocean views, family-friendly activities, and the charming atmosphere of the Whimsy Waterfront. With its friendly locals and ample recreational opportunities, Ocean Pines offers a perfect blend of relaxation and adventure for a memorable vacation experience.

  • Ocean City: Located 9.7km from Ocean Pines, Ocean City is a vibrant coastal city known for its stunning boardwalk and family-friendly atmosphere. Visitors can indulge in outdoor activities, romantic strolls, and exciting family experiences. The famous boardwalk is lined with shops, restaurants, and amusement rides, while the nearby sandy beaches offer a perfect spot for sunbathing and water sports. Don't miss the local attractions, including the Esplanade and the delightful family beach, which provide endless opportunities for fun in the sun.
  • Isle of Wight: Just 4.8km from Ocean Pines, Isle of Wight is a scenic island retreat that invites adventure seekers and nature lovers alike. This picturesque destination is perfect for outdoor enthusiasts, offering lush landscapes and stunning vistas. Visitors can enjoy a round of golf at one of the island's renowned courses, explore the family-friendly beaches, or immerse themselves in the serene beauty of the nature reserve. The tranquil surroundings make it an ideal getaway for those looking to reconnect with nature.
  • Midtown Ocean City: Situated 8.0km from Ocean Pines, Midtown Ocean City is a charming neighbourhood that offers a delightful mix of outdoor activities and family fun. With easy access to the bustling boardwalk, shopping areas, and water parks, this area is perfect for those seeking both relaxation and excitement. Local landmarks such as the Esplanade and family beach provide a welcoming atmosphere for all ages. Whether you're enjoying a romantic evening or spending time with family, Midtown Ocean City has something for everyone.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you might enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, feel free to utilize our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s unique Trip Board offers you a dedicated area to plan exciting new trips, pick up right where you left off, or view and manage your travel arrangements. You can easily access properties you’ve saved or booked in the sections for Potential, Upcoming, or Current Trips. To explore Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Ocean Pines?
Based on our research, houses are the most desirable type of vacation rental in Ocean Pines. But of course, everyone's idea of the perfect stay differs. Vrbo has vacation rentals of all sizes and shapes, and we'll help you to find the perfect match.
How much does it cost to rent a vacation rental in Ocean Pines?
Property type, length of stay and season are some of the conditions that can influence the price of a vacation home. Simply click on your travel dates to find your perfect fit. From comfy cottages to expansive luxury villas, all Vrbo vacation rentals provide unbeatable value.
How much does it cost to rent a beach house in Ocean Pines?
Prices for beach houses in Ocean Pines vary depending on the style and size of the property and time of year you're traveling. Simply enter your dates of travel into Vrbo and the number of guests to view vacation rental options and prices. From there you can use our filters to refine your search results by nearby activities, ratings, amenities and more.
Are there pet-friendly vacation rentals in Ocean Pines?
Pack up a suitcase for the pooch in your life because Ocean Pines has 173 stays that welcome pets with open arms. Let your four-legged pal join in on the family trip at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates then check the "Pets allowed" filter box.
Can I rent a house with a pool in Ocean Pines?
Grab your swimsuit and pool noodle, because there are 128 houses with a private pool in Ocean Pines. Stay at one of these superb vacation rentals and you'll enjoy pool days every day. Simply enter your dates into Vrbo, then check the "pool" filter to find a place to make a splash!
What are popular rental amenities in Ocean Pines?
A nearby waterfront, a lake view and a swimming pool are the most popular rental amenities in Ocean Pines. Whether you're taking a trip by yourself, with your other half or a bunch of friends, Vrbo can help you find a vacation home that suits your style with all the features you'll enjoy.
Are there large group vacation rentals in Ocean Pines?
You can choose from 44 vacation rentals in Ocean Pines that can host a group of 10 or more people. Whether you're organizing a vacation with extended family or a celebration like an anniversary, there's ample space to get your favorite people together under the same roof.
Are there vacation rentals in Ocean Pines that welcome kids?
With 173 family-friendly vacation homes to choose from in Ocean Pines, now is the perfect time to introduce your little ones to the pleasures of travel. Simply click on our "Properties good for families" filter to look for stays that feature conveniences perfect for families on the move, such as multiple bedrooms, pools, hot tubs and bunk beds.
What are the top attractions for families in Ocean Pines?
Keeping the kids entertained during your stay in Ocean Pines is simple with these top family-friendly attractions:

  • Frontier Town Water Park and Golf
  • GlenRiddle Golf Club
  • River Run Golf Club

Are there one-bedroom vacation rentals in Ocean Pines?
Yes, there are two one-bedroom properties in Ocean Pines to pick from. A one-bedroom vacation rental is a great option if it's only two of you or if you're vacationing alone. Add in more convenience, space and privacy compared to a hotel, and you've got the makings of an unforgettable trip.
Can I find two-bedroom vacation rentals in Ocean Pines?
Choose from 14 two-bedroom homes in Ocean Pines. Settle the kids into the second room or fill it with a couple of your nearest and dearest friends. There's a spot for whoever's lucky enough to be joining your journey.
Are there vacation rentals with WiFi in Ocean Pines?
Whether you want to keep up with the headlines, make a video call or update your social media accounts, there are 41 vacation homes with WiFi in Ocean Pines. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.
How can I find vacation rentals with air conditioning in Ocean Pines?
Ocean Pines has 166 vacation rentals where you'll be able to spend your days in air-conditioned comfort. To find a stay on Vrbo that features this amenity, enter your desired travel dates and use the convenient filters to select the "air conditioning" box.
How old do you have to be to rent a vacation rental in Ocean Pines?
The minimum age requirements can differ across properties on Vrbo, so be sure to check the rules of the vacation rental in Ocean Pines you want to book. But typically, it's 16, 18 or 21.
How long can I rent a vacation rental in Ocean Pines for?
The amount of time you can rent an Ocean Pines vacation home for is down to each property. Just put in your dates of travel to see available options offering longer term stays. They come with all the things you need to make your extended break more enjoyable and convenient, such as kitchens and air conditioning. Some vacation homes may also offer weekly or monthly discounts, so you can stick around for longer for less.

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