
Ocean Pines vacation rentals
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Top-rated vacation rentals in Ocean Pines
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Popular amenities for Ocean Pines vacation rentals
Ocean Pines vacation rentals near the ocean

Oceanfront Condo w/ Direct Beach Access
We enjoyed our stay. Condo is clean and has a lovely view of the ocean. We will be back.

Ocean and Bay views with a pool
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!

Ocean Front 802 Midtown Oasis Pool & Parking
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.

Close to beach, away from crowd
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.

Amazing oceanfront view 3 blocks from boardwalk
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!

Sandy Sheets cozy beach cottage
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.

Oasis by the Ocean - Direct Oceanfront
Amazing stay ! Very responsive hosts. Place was quaint and cute. We will be back !

Direct Ocean Front/Gorgeous Views/Indoor Pool
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

Wight Bay Unit 245
Jenna’s place is great, very clean and spacious. And a super relaxing space, I highly recommend it

Ahoy Condo! Great ocean view just steps to beach!
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.

Spacious Direct Oceanfront 1BR Condo w/Balconies
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.

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

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

Lovely Large 3 Bedroom Bayfront Condo in Midtown!
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!

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

Charming Remodeled 2 level condo w/ amazing views
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

Central Haven with Great Fenced Yard
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.

New 5 Bdrm/Bayside Home/Prime Spot/Private Parking
The house was huge and super clean! It was great for our large group.

70th St. Oceanside Townhome !
Very clean, nice place to stay with family!

The Laurel House - Large fenced in yard!
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

Beaches Near By
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!

Cedar Dr & Central Av 3 bedrooms Millville house
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.

Newly built, modern home, short walk to the beach
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.

Home in Ocean View (Bethany Beach) Delaware
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.
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- Ocean City Beach
- Broadkill Beach
- Assateague Island National Seashore
- Cape May Beach NJ
- Mile Beach
- Higbee Beach
- Miami Beach
- Poverty Beach
- Ocean City Boardwalk
- Dewey Beach Access
- Big Stone Beach
- Jolly Roger Amusement Park
- Northside Park
- Willow Creek Winery & Farm
- Poodle Beach
- Cape Henlopen State Park
- Heritage Shores
- Jolly Roger at the Pier
- Towers Beach
- Delaware Seashore State Park
- Killens Pond State Park
- Bayside Resort Golf Club
- Wallops Beach
- Bow Beach
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