Ocean Pines vacation rentals

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Popular amenities for Ocean Pines vacation rentals

Stay near Ocean Pines's top sights

Ocean Downs Casino34 locals recommend
Ocean Pines Yacht Club & Marina24 locals recommend
Crabs To Go12 locals recommend
Glen Riddle Golf Club11 locals recommend
Ocean Pines Golf Club15 locals recommend
Southgate Grill9 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 stars7 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, 306 reviews

Ocean Front 802 Midtown Oasis Pool & Parking

StephanieRating, 5 stars1 week ago
Katherine’s place is a great stay! The view from the balcony is lovely and the photos online are accurate. The bed was also probably the most comfortable bed we’ve ever had at an Airbnb. The location is just a few blocks from the start of the boardwalk and there are many restaurants within quick walking distance. It is very closer to one of the Jolly Roger locations that has a water park and a go kart section. It is however a longer walk (over 30 blocks) from the busiest part of the boardwalk. Because of this though it makes the are much quieter so it all depends on what you are looking for. We loved our stay and would absolutely stay again! In addition Kathryne was very responsive and even ordered and extra fire stick for one of the rooms so we could try and get Disney+ in there for our kids - above and beyond. Thank you for a great stay.
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, 108 reviews

Amazing oceanfront view 3 blocks from boardwalk

RebeccaRating, 5 stars2 weeks ago
We had a wonderful time at John‘s condo! The location can’t be beat and it offered everything we needed. We had little issue with the dishwasher and washing machine, but John responded very promptly and took care of everything quick as could be. Highly recommend!
Superhost
Cottage in Ocean City
4.85 out of 5 average rating, 27 reviews

Sandy Sheets cozy beach cottage

Mary JoRating, 5 stars8 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 stars7 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, 119 reviews

Direct Ocean Front/Gorgeous Views/Indoor Pool

SusanRating, 5 stars3 days ago
The view from the living room was absolutely beautiful (even on a rainy day), and the location is close to a lot of restaurants and activities. The beds were very comfortable and the linens were super soft! However, although coffee was supplied for the coffee maker, the k cups were all decaf and there was only one creamer packet for the 3 of us to share. And the wine glasses were plastic, but we substituted with hi-ball (glass) glasses. We got in late the night we checked in, so we made due (didn’t want to bug the host 11:30pm) but that was our only disappointment.

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 stars7 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, 267 reviews

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

AbdelaliRating, 5 stars3 days ago
Adam was a pleasure to deal with. He was extremely proactive, responsive and looked out for our best interest. Can’t ask for a better interaction. The property was easy to find and close to everything. Great restaurants….beach views from the living room and master bedroom. My family and I have stayed at a few gorgeous properties in Ocean City but this place is definitely the best bang for your buck! Thanks for such a pleasant interaction and for being a great host. Your hosting is 5 star.
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 3 Bedroom Bayfront Condo in Midtown!

JoseRating, 5 stars9 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 stars9 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, 103 reviews

Charming Remodeled 2 level condo w/ amazing views

SydneyRating, 5 stars2 weeks ago
Blanca has an absolutely beautiful home. The location is close to the beach, food and lots of activities. The set up of the condo is perfect for families, especially those with small children. It was extremely clean and was stocked with cooking and cleaning supplies. I highly recommend her place for your next stay in Ocean City and hope to come back with my family in the future!

Ocean Pines house rentals

Guest favorite
Home in Selbyville
4.95 out of 5 average rating, 110 reviews

Central Haven with Great Fenced Yard

HollyRating, 5 stars1 week ago
Felt right at home from the minute we walked in and so did our pup! It’s very dog-friendly, they even have dog bowls out if you need them. There was a big thunderstorm at night and the house felt sturdy and peaceful. Also very comfortable pillows and bedding. I would recommend bringing an extra blanket if it’s colder out because the quilts are light summer-weight. Beautiful and private backyard, very nice and welcoming place.
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 stars7 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 stars7 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 stars2 weeks 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 stars8 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 stars9 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 stars9 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 stars8 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 house rentals in Ocean Pines?

    Ocean Pines has more than 230 family-friendly house 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