
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
Fantastic stay for my wife and I's anniversary, host was incredibly kind, and the condo was everything we wanted and more! So close to the beach, and in such an easy to get to location! highly recommend

2nd Floor 3 BR Condo Close to the beach with Pool!
Wonderful place and a hidden gem for the price. Definitely will be back.

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.

Driftwood Condo, 1BRTropical Bayside w/sunsetview
Hand down what an AIRBNB is supposed to be. The place is just like the pictures and smells crystal clean upon arrival. The mattress and linens were so comfortable it had me wanting to replace my mattress! This was the perfect place for annual girls weekend. Let me explain how gracious they were. We had previously picked a different Airbnb and the moment we walked into the place realized we had been PUNKED. I wont get into that whole story but needless to say it was nothing like what was advertised and we actually felt unsafe. I reach out to Steven immediately and he responded right away. Although the reservation would mean us checking in within hours of the booking he was willing to accommodate us with very short notice. The communication was flawless and Steven was truly our saving grace for the trip. What turned into a rough start ended on a very high note. Thank you, again Steven!

July 4th week & Country Calling Weekend Available
This property was well appointed and very comfortable. The view from the unit was spectacular with views of Assateaque Island and Assawoman Bay. Loved being able to enjoy the sunsets. I appreciated the balcony shade so much in the afternoons. The kitchen was well stocked with everything I needed. Easy walk or bike ride to the boardwalk and inlet activities. The pool was private and well maintained. Would definitely consider booking 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!

Relaxing Breezy Seaside 3bd/2ba/2decks King Bed
Cozy little beach spot. Shelly was so responsive and helpful! Would 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.

Bayside - Waterfront - Dock - Quiet Area
This home was such a lovely place to stay — cute, clean, and wonderfully relaxing. The space was spotless and had a warm, welcoming vibe that made us feel right at home. One thing to note is that the linens and towels were delivered separately, so we had to put them on ourselves. That said, it was actually reassuring to know they were freshly cleaned and untouched. Overall, it was a peaceful and comfortable stay, and I’d happily come back again. Highly recommend!

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
Absolutely beautiful home with the most amazing home. Everyone felt right at home with just enough space for my friends and family. Best way to spend my birthday !

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!

Beautiful Waterfront Home-Private, Clean, Relaxing
Peaceful setting to get away for the week. We had a small issue occur while staying at the house and Laura took care of it that day. She was timely with responding and communicating with us. The kids had a great time at the dock catching crabs and minnows. The pool was nice to have access to as well. We would stay here again.
Waterfront condo rentals

Cozy beach side condo
Great place! It was spacious, quiet, and well appointed. It was nice to have all linens in a sealed clean bag, ready to put on the bed. We couldn’t have asked for a better stay!

🏖 *Ocean *Ocean *Ocean* 🏖 Beautiful Condo!!
Our stay was amazing, and Adam was communicative and extremely helpful the entire stay! Beautiful place and great location.

🌊Oceanfront studio w/ amazing views & amenities🏖
I had a peaceful, relaxing time and enjoyed the ocean view and the sound of the waves. Lisa was extremely communicative and made sure I had everything I needed for a great stay.

Direct Ocean Front/Gorgeous Views/Indoor Pool
My husband and I decided to go on a getaway last minute. We found Seth’s place and were able to book the unit for the days we had available. It was great and met all of our expectations. We have been to OC and Fenwick many times and knew this is where we wanted to stay. It did not disappoint and we hope to rent again in the near future.

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!

Lovely Turnkey Ocean Block Condo in Ocean City
We loved our stay in Eka's home! We were only there for a couple of days, but it felt very comfortable for 3 of us. It was VERY clean and they provided everything you could need! I really loved just packing my clothes and some snacks and not worrying about towels, sheets, pillows, blankets, soap, etc. They even have beach towels and chairs! It was a great distance to the beach and right in the middle of coastal highway. Eka and her husband were very responsive and helpful. THANK YOU for a wonderful stay. We will definitely keep this place in mind the next time we travel to Ocean City. :-)

DirectOceanFront on Boardwalk/Newly Remodeled/Pool
the location was perfect for our families needs. easy access to the boardwalk. spectacular ocean views.

Sand Haven - Just Steps to the Sand
Great place right on the beach and close to everything, thanks!
Quick stats about waterfront rentals in Ocean Pines
Total rentals
60 properties
Nightly prices starting at
R1,622 ZAR 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
- Willow Creek Winery & Farm
- Northside Park
- Towers Beach
- Assateague Beach
- Jolly Roger at the Pier
- Bayside Resort Golf Club
- Poodle Beach
- Delaware Seashore State Park
- Pearl Beach
- Wildwood Dog Park & Beach
- Peninsula Golf & Country Club
- Heritage Shores
- Killens Pond State Park