Ocean Pines vacation rentals

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Popular amenities for Ocean Pines vacation rentals

Stay near Ocean Pines's top sights

Ocean Downs Casino44 locals recommend
Ocean Pines Yacht Club & Marina28 locals recommend
Crabs To Go18 locals recommend
Glen Riddle Golf Club16 locals recommend
Ocean Pines Golf Club16 locals recommend
Southgate Grill14 locals recommend

Ocean Pines vacation rentals near the ocean

Superhost
Apartment in Ocean City
4.93 out of 5 average rating, 28 reviews

Oceanfront Condo w/ Direct Beach Access

MelissaRating, 5 stars6 months ago
We enjoyed our stay. Condo is clean and has a lovely view of the ocean. We will be back.
Top guest favorite
Condo in Ocean City
5 out of 5 average rating, 12 reviews

Ocean and Bay views with a pool

DouglasRating, 5 stars8 months ago
This condo is clean and modern with plenty of space. The four of us had plenty of room and all the amenities we needed for a comfortable stay. It is located a short ten-minute walk from one of the best restaurants in Ocean City and a two-minute walk to the dune crossing for the beach. The view of the Bay and Atlantic is very good. Sunsets over the Bay are spectacular. We had a minor issue, that was quickly resolved by our host, Leland. The early check in was greatly appreciated since it was quite warm when we arrived. It’s a great place to stay and we would definitely return as schedules allow. Stay here, you won’t be sorry!
Guest favorite
Condo in Ocean City
4.91 out of 5 average rating, 305 reviews

Ocean Front 802 Midtown Oasis Pool & Parking

MoniqueRating, 5 stars3 days ago
I enjoyed staying at this location. The view once you enter the condo is fantastic. Access to the beach and to other ocean city restaurants are great very walkable or very very short drive . The building is undergoing some kind of construction so when you walk into the building it’s clearly being worked on and is a bit dusty but once you get in the condo everything melts away. The condo also comes with some beach chairs and umbrellas.
Superhost
Home in Ocean View
4.75 out of 5 average rating, 4 reviews

Close to beach, away from crowd

NicholasRating, 5 stars8 months ago
This place exceeded our expectations. Our family and dog absolutely loved it . The house was clean and ready for us upon arrival. Everything was within driving distance. After busy long days we came back to a nice and quiet area and slept well. The beds were so comfortable. Loved that we all had our separate bathrooms and had enough space. Highly recommend staying. We enjoyed our stay. Yue was welcoming and kept in communication throughout our stay.
Guest favorite
Apartment in Ocean City
4.86 out of 5 average rating, 105 reviews

Amazing oceanfront view 3 blocks from boardwalk

KenyadabakerRating, 5 stars2 weeks ago
So first of all I haven’t been on vacation in 5 years lol. This place was absolutely wonderful my daughter and I enjoyed our stay. Lots to do and we felt right at home I 1000% recommend!
Superhost
Cottage in Ocean City
4.85 out of 5 average rating, 27 reviews

Sandy Sheets cozy beach cottage

Mary JoRating, 5 stars7 months ago
This is the second time we’ve stayed there so that should tell you something. There are plenty of bedrooms and beds. A wonderful size porch, where the family can gather. The location is the best.
Superhost
Condo in Ocean City
4.89 out of 5 average rating, 102 reviews

Oasis by the Ocean - Direct Oceanfront

SophiaRating, 5 stars6 months ago
Amazing stay ! Very responsive hosts. Place was quaint and cute. We will be back !
Guest favorite
Condo in Ocean City
4.97 out of 5 average rating, 118 reviews

Direct Ocean Front/Gorgeous Views/Indoor Pool

JanetRating, 5 stars3 weeks ago
Seth was extremely responsive and accommodated us for a last-minute getaway, making for a seamless experience. The condo has a lovely view of the beach and ocean, which made for a relaxing spot to start or end the day. This condo was a perfect long-weekend getaway spot for us in the off-season and was equipped nicely for in-season use.

Ocean Pines condo rentals

Guest favorite
Condo in Ocean City
4.91 out of 5 average rating, 272 reviews

Wight Bay Unit 245

JeremyRating, 5 stars7 months ago
Jenna’s place is great, very clean and spacious. And a super relaxing space, I highly recommend it
Top guest favorite
Condo in Ocean City
4.98 out of 5 average rating, 113 reviews

Ahoy Condo! Great ocean view just steps to beach!

PatrickRating, 5 stars8 months ago
This was a great place to stay. It's on the north end of Ocean City, so we'll removed from a lot of the touristy stuff. Really great access to the beach that had lots of open space and absolutely no crowding. The place was well appointed and very comfortable.
Superhost
Condo in Ocean City
4.78 out of 5 average rating, 105 reviews

Spacious Direct Oceanfront 1BR Condo w/Balconies

BrandonRating, 5 stars6 months ago
An amazing place! Double balconies for sunrise and sunset views. Very peaceful and friendly neighbors. Everything within walking distance. Would highly recommend! Natasha was very quick to respond to any questions or needs you may have.
Superhost
Condo in Ocean City
4.82 out of 5 average rating, 265 reviews

🏖 *Ocean *Ocean *Ocean* 🏖 Beautiful Condo!!

AaronRating, 5 stars1 week ago
Had a great stay at Adam’s place. Amazing view and really comfy couch and beds. The kitchen is nice, the dining room area is perfect. Our oldest loved having the bed in the covered deck area. We got to use our binoculars and see dolphins in the ocean. Adam is a super helpful and friendly host. We will be back!
Superhost
Condo in Ocean City
4.93 out of 5 average rating, 44 reviews

2BR/2BA/ 5 Bed condo with 2 private balconies!

PatriciaRating, 5 stars6 months ago
Another great stay. The location can't be any better, central OC at it's best. Easy walk to the beach. We tried Barrio Taco this time, it's huge, recently remodeled. Dead Freddie's across the street is a plus. Plenty of room for our family. We'll be back! Raif went above and beyond with his hospitality - thank you.
Guest favorite
Condo in Ocean City
4.85 out of 5 average rating, 46 reviews

Lovely Large Bayfront!

JoseRating, 5 stars8 months ago
Amazing view from the deck and living room of the bay - we spent quite a lot of time just watching nature outside. Beach entrance was right across the street, walkable and near great restaurants and boutiques. Unfortunately, we missed the linens/towels info in the listing but Steve was able to recommend a local company to bring those items to us. We also enjoyed the rooftop pool that was part of the building while not at the beach. If you are looking for a centrally located rental in Ocean City we would highly recommend this property!
Superhost
Condo in Ocean City
4.85 out of 5 average rating, 55 reviews

Ful Dek - Family Casual Condo-Midtown-Ocean Block!

JadeRating, 5 stars8 months ago
Really have no complaints about Jen’s place!!! There is so much space, it’s very cozy and homie. TVs in every room. The deck is so cute to sit outside and play some games or eat breaker/dinner. You have two parking spots, access to the beach and many restaurants around you. The bus stop to take you to the boardwalk is not a far walk either so you have unlimited access to everything you need. This was my first time back to OC MD in a long time and Jen’s place was the right place. 10/10 and will hopefully be staying again soon 😁
Top guest favorite
Condo in Ocean City
4.87 out of 5 average rating, 102 reviews

Charming Remodeled 2 level condo w/ amazing views

MaryRating, 5 stars2 weeks ago
This was but far, one of the cleanest and most well appointed places we have stayed in Ocean City! Besides plentiful cleaning and cooking supplies, the bathrooms were also stocked with toilet paper, hair dryers and toiletries should you need any! Nice job Blanca!!

Ocean Pines house rentals

Guest favorite
Home in Selbyville
4.94 out of 5 average rating, 107 reviews

Central Haven with Great Fenced Yard

ShayanaRating, 5 stars2 weeks ago
Sharee’s place was a dream. We bought our dogs and infant son and I couldn’t have asked for a more perfect stay. There were clean towels and linens in every room, the kitchen was fully stocked (which was important to us because we cooked breakfast, lunch, and dinner most days), and bathrooms were spotless. Beds and all furniture were extremely comfortable and sturdy. We traveled to Ocean City and Rehobeth and both locations were really close. It was always nice to come back to a peaceful neighborhood and home. Neighbors were also really friendly, so that’s a plus! We’ll be back and I wouldn’t hesitate to recommend to anyone interested.
Guest favorite
Home in Ocean City
4.89 out of 5 average rating, 18 reviews

New 5 Bdrm/Bayside Home/Prime Spot/Private Parking

MeghanRating, 5 stars6 months ago
The house was huge and super clean! It was great for our large group.
Top guest favorite
Home in Ocean City
5 out of 5 average rating, 8 reviews

70th St. Oceanside Townhome !

BrookeRating, 5 stars6 months ago
Very clean, nice place to stay with family!
Top guest favorite
Home in Ocean City
4.98 out of 5 average rating, 162 reviews

The Laurel House - Large fenced in yard!

MikeRating, 5 stars3 days ago
me and my wife stayed here with our 2pups willow and mazie. place was AMAZING for the dogs. fenced in back yard in and wrap around front porch that we ALL could enjoy neighbors were wonderful people and Dog lovers ❤️. James was a GREAT HOST. we actually got to meet him in person. I wish we could have spent more time talking. locationis KEY. run the dogs at fenwick beach then hop down downtown to plenty of restaurants and bars...we will definitely be back...thank you james
Superhost
Home in Frankford
4.76 out of 5 average rating, 92 reviews

Beaches Near By

SavannahRating, 5 stars7 months ago
This place will make you feel right at home in a safe neighborhood! We came down to go boating and there is a boat launch minutes away. Also restaurants and grocerie stories only about 10 minutes away. Easy to check in and very comfortable!
Guest favorite
Home in Millville
4.85 out of 5 average rating, 60 reviews

Cedar Dr & Central Av 3 bedrooms Millville house

ChuckRating, 5 stars8 months ago
Very happy with our stay, close to grocery and restaurants. Owner communicated very well and had great recommendations. The house had great spaces for our group of 7 to spread out or all hang together. Thanks again for your hospitality.
Superhost
Home in Ocean City
4.92 out of 5 average rating, 48 reviews

Newly built, modern home, short walk to the beach

JulieRating, 5 stars8 months ago
Second stay for us and we would go back again. We love that we can walk to the beach. Plenty of space for two families with young adult children. The screened in porch is great for morning coffee and relaxing in the evening. Hosts are super responsive and flexible.
Guest favorite
Home in Ocean View
4.91 out of 5 average rating, 54 reviews

Home in Ocean View (Bethany Beach) Delaware

KateRating, 5 stars7 months ago
The house is way bigger than what’s shown in the pictures. Two of the five bed rooms have private bathrooms which is a big plus. The house doesn’t come with linen so you need to bring your own.

Quick stats about vacation rentals in Ocean Pines

  • Total rentals

    280 properties

  • Nightly prices starting at

    $40 before taxes and fees

  • Total number of reviews

    7.6K reviews

  • Family-friendly rentals

    260 properties are a good fit for families

  • Pet-friendly rentals

    80 properties allow pets

  • Rentals with a pool

    140 properties have a pool

Your guide to Ocean Pines

All About Ocean Pines

What started in 1968 as a small resort on Maryland’s Easter Shore has grown into a thriving seaside community with swimming pools, walking trails, a yacht club, and a marina ripe for stand-up paddleboarding, kayaking, and canoeing. Ocean Pines is home to a network of canals that offer direct access to the water for some residents.

At nearby Ocean City, just five miles away, you can stroll the boardwalk or go for a swim along the 10 miles of beaches. Amusement parks offer thrill rides and arcade games, and you can head over to Ocean City Life-Saving Station Museum to learn about the historic role performed by the United States Life-Saving Service. Ocean Pines is also less than 30 minutes away from the stunning Assateague Island, a National Natural Landmark known for its pristine landscapes and wildlife, including white-tailed deer, river otters, and muskrats.


The best time to stay in a vacation rental in Ocean Pines

The Ocean City area is an extremely popular summer destination thanks to the beautiful weather and sandy beaches. Accommodation options may be limited during this time so it is a good idea to book early. Fall and spring tend to be much quieter, and you may find that many of the amenities in Ocean Pines are largely empty on weekdays, as well as the Ocean City Boardwalk and beaches. Ocean City holds its annual Sunfest at the end of September, offering activities like arts and crafts as well as a variety of food.

During the winter, it gets very quiet in Ocean Pines, and many local businesses close for the season. However, this is still a great time to book an Ocean Pines rental as you can explore the nearby beaches and parks in solitude. There is also a farmer’s market held every Saturday to stock up on fresh produce and artisanal products. There are even themed markets for Halloween, Thanksgiving, and Christmas.


Top things to do in Ocean Pines

Assawoman Bay

Twenty minutes outside of town, Assawoman Bay is a lagoon located on the northern end of Baltimore. It is a popular destination for many water activities, including boating and fishing. The most popular catches here are summer flounder, bluefish, and Atlantic stingray.

Ocean City

Located just a short drive from Ocean Pines, Ocean City offers all the bustling activities and attractions of a large resort city. Here, you can visit one of the many amusement parks such as Jolly Roger, watch the sunset on the boardwalk, or grab crab cakes and drinks at one of the local bars and restaurants.

Assateague Island

This gorgeous uninhabited island stretched between Virginia and Maryland offers some of the area’s most pristine beaches and natural landscapes, including salt marshes and maritime forests surrounding the island’s stunning bays. It is a great spot for hiking and wildlife viewing and while you are there, you may even be able to see the island’s wild ponies.

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Ocean Pines?

    Yes! Work meets play with ease at over 130 vacation rentals in Ocean Pines featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Ocean Pines?

    Four-legged friends are welcome in Ocean Pines. Choose from more than 80 vacation rentals for guests traveling with pets.

  • Are there Ocean Pines vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 140 vacation homes with pools in Ocean Pines, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in cottage rentals in Ocean Pines?

    Experience the best of Ocean Pines with our cottage rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Ocean Pines have a bbq area?

    Absolutely! We offer over 60 house rentals with a bbq area in Ocean Pines. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Ocean Pines have a gym?

    Absolutely! We offer over 20 house rentals with a gym in Ocean Pines. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Ocean Pines have self check-in?

    Absolutely! We offer over 80 house rentals with self check-in in Ocean Pines. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly cottage rentals in Ocean Pines?

    Ocean Pines has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Worcester County
  5. Ocean Pines