
Waterfront vacation rentals in Ocean Pines
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Top-rated waterfront rentals in Ocean Pines
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Popular amenities for Ocean Pines waterfront rentals
Waterfront apartment rentals

StayAhoy! | Steps to Beach | Ocean View
We had such a comfortable stay with all the amenities we needed as a family! It was a great location to nearby restaurants, stores, and grocery store, and a real bonus to walk just a short distance away to the beach that had a lifeguard. The place was also just a half an hour or so drive to Assateague Island National Seashore, where we were able to see wild ponies. Communication with the host was excellent.

Canal Front Condo 2 Blocks 2 Beach & Park Sleeps 4
Kathy and Johns place had an easy check in process. The house is very nice and clean. It was just the right size for the 2 of us. The house is very clean and located mins from the beach. It rained two of the days we were there. We stayed in, the area is very quiet and relaxing. Kathy or John was very responsive if we had any questions. If we go back, I would love to stay here again.

Bayside Bungalow - Waterfront
Identical to pictures! Beautiful rental in convenient location. The beach and boardwalk were easily walkable and having Fish Tales next door was convenient! My only suggestion would be is to bring an eye mask if you are a light sleeper, there are no shades on kitchen windows so it’s very bright in the early morning since it’s all connected. It helped us to get up and moving in the morning so we didn’t mind. Morgan was quick to reply to messages and a very gracious owner! We will definitely be back.

Amazing oceanfront view 3 blocks from boardwalk
Condo was exactly as described! Amazing oceanfront view! I was also impressed with how much room there was. It was cruiser week so it was a tad bit noisy at night, but other than that and the fact we couldn’t stay longer, we had a wonderful time and enjoyed our stay!

Endless Summer With Ocean View & Large Deck
Laura was a very responsive and wonderful host! She went above and beyond with providing a variety of things to do and see during our stay. She also made sure the check in and check out process went smoothly. The home was well kept, clean and had a great view! Being able to relax on the back porch with the sound of the waves was so peaceful. Our family had a great stay and will definitely be back! Thank you Laura!

Luxurious Renovation 2024|Ocean Front|Indoor Pool
We had a wonderful stay at this condo. Perfect location, great views, recently renovated and extremely clean. Jason was fantastic and quickly helped us find a workaround when the building pool was unexpectedly closed. We would definitely stay here again!

Beautiful Bayfront Condo!
The condo was perfect for our family of 8. It is much larger than the pictures let on. The deck was big enough for all of us to comfortably sit and chat - and Julie has plenty of patio chairs and two tables! Everything was super clean, no clutter, lots of space to spread out and not be on top of each other. The location is perfect too! Quick walk to the beach and some shops. Bus ride can easily take you down to the boardwalk or restaurants you can’t walk to. No need to move your car once you are here. We enjoyed this stay so much we are planning on returning next year. Thank you Julie for sharing your home with us!!

SuperHost! Amazing OceanFront View with 2 Pools!
I was so impressed with Kara’s condo. It was everything I hoped it would be. The decor is very nice and the kitchen is wonderful— modern, spacious, and containing anything you need for cooking or entertaining. The view of the ocean from the 19th floor is both spectacular and calming, whether on the spacious balcony or looking down through the bedroom’s floor to ceiling windows. The building is great. Everyone was friendly and this is a very nice part of Ocean City. Lastly, Kara was terrific. Kind and a great communicator. Plus check in was smooth. If you’re considering a two bedroom, two bathroom condo in this area, I highly recommend this listing!
Waterfront house rentals

Private pool, waterfront, kayaks, bikes, firepits!
We can't wait to return to Golden Quarter Farm! Charming and expansive, the property has everything we were looking for in a place to spend a relaxing weekend with extended family. The historic house is bright and roomy with a well-appointed kitchen; the bedrooms are unique, comfortable, and private; and the living space homey and inviting -- perfect for spending time together. The beautiful views of the riverfront drew everyone outside for walks down the pier, through the fields, and down the sun-dappled forest trails. It was a bit too chilly during our April stay, but the possibilities for enjoying the river (canoe, kayay, SUP) and lovely pool were nonetheless enticing. Finally, I must mention that Evie and Mary were extraordinarily welcoming and accomodating, from communicating proactively to preparing the home for our stay and checking in to make sure everything was perfect. Highly recommend!

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB
Beautiful spot! Great location, close to all the happenings of Ocean City, but peaceful and quiet at the house…perfect set up. Great neighborhood. The house is beautiful, all the beds very comfortable. The back deck is gorgeous, thoroughly enjoyed that space and taking the kayaks out on the canal! It’s worth bringing your own linens and towels, we packed everything into a large tote and it worked out perfectly. Very responsive and friendly host! We had a great time here and plan to return. Highly recommend!

Waterfront Coastal Casual + Dock + Dog-Friendly!
Jill’s vacation home was perfect for our family of 7 adults and 5 kids ages 1-13. The house was very clean and super cozy! Our family visited for Thanksgiving and we were able to prep our entire meal in the well-stocked kitchen and had room for all of us to sit to eat. The family room and kitchen area were large enough for us to all to play games, watch tv, and for the kids to play with their toys. The location was perfect, close to everything but far enough away to be able to sit outside peacefully (even though it was cold!) or take walks from the property. Jill was a wonderful host and made sure we had everything we needed for our arrival. I would highly recommend this vacation rental! This was definitely one of the best vacation rentals we’ve stayed in.

Direct Ocean Front - Beach Retreat Condo!
We had a wonderful stay at Chris and Loreees place! Super responsive when needed and clear instructions for check in and out. Private, quite, clean building and condo and we had everything we needed. The views were stunning & exactly as pictured. Walking distance to many stores, restaurants, and 7-11 next door for convenience. I would recommend staying here!

Bayfront Sunset Sanctuary @ Stone Harbor
They how was very clean and was not far from local attractions and the views was tranquil

Ocean City Paradise, Large Outside Deck, Bar&Grill
Cute and accommodating! The space was very clean and equipped with easy to use amenities. Truly felt like a home away from home. We really enjoyed the tranquility of the outdoor space, and how conveniently located we were to the beach, shopping, and restaurants. Would definitely stay again!

Villa Caribbean OCMD
Out of all the places we’ve stayed this felt the most at home. Beautiful views, waking up on the water and seeing it from the moment you open your eyes and walk to the next room is priceless. This place far surpassed our expectations, the host was wonderful and promptly responsive. We WILL be back!

Mosaic Life Escapes -Bayfront Million Dollar Views
Stayed for the weekend after Thanksgiving and it was a great experience. The house was cozy, the beds were comfortable, and the bathroom shower was awesome. The best part of the house is the view out over the bay. It’s really peaceful and a great spot to have coffee and watch the sunrise. We will definitely stay here again!
Waterfront condo rentals

Mid OC Bayside Canal Condo Remodeled-Pets Welcome!
Kathleen’s place was perfect for our weekend trip to ocean city. The apartment was very clean and comfortable. The neighborhood was great for walking our dog and was in a nice location-only a 15 minute walk to the beach! We had a great stay.

The Sunset House-Bayside-3 min drive to Beach
I had a great stay at Serafima’s place. The space was clean and exactly as described in the listing. It had everything I needed for a comfortable visit, and the setup was thoughtfully arranged. The location is excellent—close to great restaurants, and plenty of local attractions. The neighborhood felt safe and was easy to navigate. Overall, it was a smooth and pleasant experience. I’d definitely stay here again and would recommend it to others visiting the area.

New Updated Direct Oceanfront Condo - Pool & Wifi!
Listing is better than you think it is! Great location (I was nervous about it because we usually stay closer to 120th St) it was very private and peaceful. Big bonus that it is right over the bridge (no extra traffic lights!) The kitchen is fully stocked - we wound up bringing a lot that we didn’t need. The pullout couch is also one of the most comfortable I’ve ever been on. Beautifully decorated and updated. Might book again this season!

Oceanfront Sea View | 46th St
Beautiful apartment. Everything was spotless and as described. Amazing views and easy beach access.

🏖 *Ocean *Ocean *Ocean* 🏖 Beautiful Condo!!
Adam was a great host, answered all questions we had in a timely manner and went above and beyond to check in to make sure we were settling in and enjoying our stay. Our daughter loved the extra amenities of toys and the bunk beds. This home provided beautiful views of the sunrise on the beach and an excellent view of the sunset on the bay. We are already planning our next stay.

Direct Oceanfront close to Northside Park!
Really enjoyed our stay at Stephanie's. Awesome condo that was clean, comfortable and roomy. Wonderful views from Living Room, Balcony and Master Bedroom. Close enough to the water to hear the waves breaking. Plenty of restaurants and shops close by. Definitely hope to be back!

Direct Ocean Front/Gorgeous Views/Indoor Pool
We had a great time at Seth’s place. The location was perfect, quiet but still plenty to do. Easy beach access and clear directions for everything. Watched dolphins from the balcony and loved hearing the waves.

Extraordinary Oceanfront Penthouse | Unit 1209
Booked a last minute trip and found this gem. Great deal, was very spacious with amazing views. Updated and decorated very nicely. Comes stocked with everything you need. Steps from the beach and close to attractions but not too close. Host was very responsive. Note: Only hang up was the pool was under construction, which was stated in the listing. Also the water line to the outside showers was cut for construction, so there’s nowhere to wash the sand off your feet. I would definitely recommend and stay here again!
Quick stats about waterfront rentals in Ocean Pines
Total rentals
60 properties
Nightly prices starting at
G$18,808 GYD before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
30 properties have a pool
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- Ocean City Beach
- Broadkill Beach
- Assateague Island National Seashore
- Cape May Beach NJ
- Mile Beach
- Higbee Beach
- Poverty Beach
- Ocean City Boardwalk
- Dewey Beach Access
- Cape Henlopen State Park
- Jolly Roger Amusement Park
- Towers Beach
- Willow Creek Winery & Farm
- Poodle Beach
- Bayside Resort Golf Club
- Northside Park
- Jolly Roger at the Pier
- Assateague Beach
- Delaware Seashore State Park
- Wildwood Dog Park & Beach
- Pearl Beach
- Peninsula Golf & Country Club
- Killens Pond State Park
- Baywood Greens Golf Maintenance