
Beachfront holiday rentals in Isle of Wight Bay
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Top-rated beachfront rentals in Isle of Wight Bay
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Pet-friendly beachfront home rentals

The Chesapeake House
We had a fantastic weekend with our adult children and their spouses. There was plenty of comfortable seating in the living room, the bedrooms and bathrooms were beautiful and we loved the outdoor patio. We had plenty of room at the table for meals and playing board games at night. We also enjoyed the proximity to the beach- very walkable.

Beach, Boardwalk n Fun- just steps to the beach
this is the … you know, i don’t even know what time at this point as my friends and i have made it a tradition to stay here twice per year for the last 3? 4? 5 years? john’s place never ceases to amaze me especially this time w/ multiple renovations including a master bedroom downstairs! can’t say enough good things, look forward to booking in the fall, thank you so much john!

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!

Direct Oceanfront Renovated Townhouse 36th Street
The place is great. Right on the beach with great decks and views — we didn’t need to put on shoes the entire time. Walkable also to lots of restaurants and other businesses. Only reason I didn’t give 5 stars on the location is not because of the house but because of the way Ocean City is structured — there really is no way to get around without going on the main, high-traffic road and few places to walk dogs comfortably in the summer when they’re not allowed on the beach. Also note you will have to make your own beds when you arrive and strip them when you leave. Other than that this place is excellent! All of us — from 5 months to 45 years and 2 dogs in between — had a great time.

A Wave From It All
Was my first time using Airbnb and Stacey made it so easy for me! She’s easy to work with and responds quickly. It is exactly as it was listed. Loved that it’s so close to the beach!

Sunset Terrace
Great stay! Close to the beach.

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines
My family really enjoyed our stay here. The house was so quaint, clean, well stocked, and all on one floor. There was plenty of space for my multi-generational family. Also, the beaches and other area attractions were nearby (just a short drive). I’d definitely recommend staying here!

Luxurious Bay Front Condo
Perfect Beach Getaway! We had an amazing stay at this condo! It was incredibly clean and spacious, with plenty of room for our family to relax. The views were stunning, and we loved being just a short walk from the beach and boardwalk—super convenient, especially with kids. The space is definitely kid-friendly, and the overall vibe was comfortable and welcoming. On top of it all, the host was extremely responsive and friendly, making the entire experience smooth and stress-free. Highly recommend for anyone visiting Ocean City!
Beachfront home rentals with a pool

Romantic Beachfront Penthouse Ocean City MD
This is the second year we stayed at this beautiful condo! Views of both ocean and the bay are spectacular!! Condo was clean and easy to access. Love the pool and beach! Close to great restaurants!! Margaret is a fantastic host!! Highly recommend this condo! We will definitely be back next year ❤️

Updated Studio,Steps to Beach,Pool
Building itself felt very secure. Owners super friendly and quick to respond while being helpful in the responses. Location was very convenient; easy to get anywhere you need and near fun places like mini golf, ice cream, good restaurants, Ron Jon etc. Would definitely recommend staying here if you’re visiting Ocean City!

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.

2bed/2bath/Pool/Next To Conv Ctr/ On Bay/Mid Town
Great place, nice decor, very comfortable beds, very well equipped, good location, very easy communication.

Top Rated! Beautful Sunsets! Midtown Bayside Condo
Raphaelle is a great host and our stay was amazing. With great views and an accommodating place, would certainly return!

Bright Oceanside Condo with Pool - Ocean City, MD
My boyfriend and I celebrated his 26th birthday at Dien’s place and it exceeded my expectations! It was so clean and Dien was incredibly responsive and went out of his way to make sure we had everything we needed. The location was perfect, right across the street from the beach and within walking distance from lots of great restaurants. He also offered us a late check out so we could enjoy every last second of our stay which was so appreciated. Overall, this was one of the best airbnb experiences I’ve had and cannot wait to come back and stay at Dien’s place again!

Updated Mid- Town Condo at Ocean City Beach!
Our stay at Adam’s condo was great. The place was clean, quiet, and had plenty of sleeping space for the 6 of us. The site pictured exactly the condo interior. Adam immediately answered any questions. Getting around was easy. We were 1 block from the beach, and drove the distance to the boardwalk amusements. We would definitely consider staying there again. The weather wasn’t the best, but we were able to go to the beach, enjoy the pool, and surrounding amusements.

Location! Location! Location!...With a view!
Matthew was a great host! Very attentive, responsive, provided great recommendations and easy instructions for check in and check out. Matthew was flexible with us for check in and check out and was very accommodating! Would definitely book with Matthew again!
Private beachfront home rentals

Ocean Front 1b/1.5ba Condo with Amazing Views!
Our weekend at Michelle’s place was absolutely perfect. First of all, her condo was so beautifully decorated and clean. We had amazing views of the beach and we listened to the waves crashing at night while one of use slept on the guest pull out couch. If you are traveling with kids, this was the perfect spot. We were conveniently located on the 3rd floor, a quick 5 min walk to and from the ocean front and the neighbors were very quiet. We also loved that we could walk to fun places to eat like Ropewalk which has cornhole and a playground for the kids! Most importantly, Michelle went above and beyond by providing us an extra blanket and pillows and answered any questions that we had very promptly. I couldn’t ask for a better experience. We can’t wait to come back again soon! Thanks Michelle.

Luxury Canal Front 2 Bedroom Condo-5 Star Reviews
We absolutely loved our stay at Kate’s place! Perfect location within walking distance of the beach, but just far away to be a peaceful neighborhood that even has a nice playground for kids. The house was equipped with everything we could possibly need, which made us feel right at home!

Beach is steps away! Oceanside Condo 46th Street
Nice condo less than a block from beach and right off main street. Jensen was a great host - very responsive and flexible.

On the Beach, On the Boardwalk, Indoor Pool!
This place was absolutely perfect! On the boardwalk with a great view from the balcony. The place was spotless and the decor was perfect. Lots of clean linens and all the luxuries of home. The host was so communicative leading up to our stay giving us great recommendations for restaurants and things to do within walking distance and also recommending things to drive to. Great stay and would absolutely stay again!

Whole renovated unit w/balcony & parking Sleeps 4
Everything was great about this place and I will come back. My wife and I enjoyed it immensley. If your coming to OC for an event such as a wedding like we did, rember to bring a hair dryer, and iron and Ironing board as they are not included. Gene does not advertise that he has them included , it was my assumption they were were included and I didn't look closely enough, but it didn't inhibit the fun we had. Just a suggestion. Also, The main bed has some broken woodedn slats in it, which pending which way we moved you could feel your self drop a little, but I brough it to his attention so I assume if he fixes that, easily, its back in business. Finally, Overall I loved this place. Clean, close to attractions, food, and the water. Other patrons in the building were freindly. Jusdt an FYI. Its is on the 3rd floor of a 4 floor condo complex and has no elevator so you should consider that if you have trouble climing stairs.

Bright Condo Close to Beach w/ Parking
I can’t say enough positive things about this place. Here’s my list of all the positives: incredibly clean, newer renovation, has a full kitchen, great shower water pressure/temp, a clean and comfortable bed, quiet location/neighbors, very short walk to boardwalk/beach, a block from the bay where the sun sets, a block from a nice pub that’s not as touristy, a guaranteed parking spot, and a host who checks in and is happy to assist! I’m sure I’m missing something(s). What a great place to stay in OCMD!

Coastal Point
Great stay, awesome location, with beautiful and clean place. Highly recommend.

Bayside Bliss-2 Bedroom,Comfort & Moments to Beach
Nomin’s place was perfect for our stay. We parked and walked everywhere. This place is close enough to stuff but far enough away that it was very quiet. We really enjoyed sitting on the balcony to drink coffee in the morning.
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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