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Condo holiday rentals in Ocean Pines

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Popular amenities for Ocean Pines condo rentals

Weekly condo rentals

Guest favourite
Condo in Ocean City
5 out of 5 average rating, 28 reviews

Mid OC Bayside Canal Condo Remodeled-Pets Welcome!

NicoleRating, 5 stars1 week ago
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.
Guest favourite
Condo in North Ocean City
4.89 out of 5 average rating, 81 reviews

Cozy beach side condo

TiffanyRating, 5 stars3 weeks ago
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!
Guest favourite
Condo in Ocean City
5 out of 5 average rating, 18 reviews

The Sunset House-Bayside-3 min drive to Beach

BrookeRating, 5 stars1 month ago
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.
Guest favourite
Condo in Montego Bay
4.98 out of 5 average rating, 41 reviews

Charming Northside Park Condo w Pool, Walk 2 Beach

AndyRating, 5 stars4 weeks ago
Julie's condo is very cozy and welcoming. It's a wonderful place for a weekend or a longer vacation. Julie was very responsive and proactive anytime my wife and I had any questions. Plenty of recommendations were provided to us so we could better plan our time in Ocean. Thank you so much, Julie! We'll be back again!
Guest favourite
Condo in North Ocean City
4.89 out of 5 average rating, 75 reviews

Golden Goose - Oceanside Condo w/Ocean & Bay views

KendraRating, 5 stars3 weeks ago
⭐️HIGHLY RECOMMEND⭐️ Everything looked exactly like the pictures. Very clean, spacious, quiet, and close to almost everything that ocean city has to offer. The kitchen is beautiful! Safe location. The beach is a few steps away. Access in and out was a breeze. I will be back! So far this place is at the top of my list in ocean city.
Superhost
Condo in North Ocean City
5 out of 5 average rating, 3 reviews

New Updated Direct Oceanfront Condo - Pool & Wifi!

KaraRating, 5 stars1 week ago
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!
Superhost
Condo in Ocean City
4.87 out of 5 average rating, 75 reviews

Oceanview Oasis with 2 private balconies

CarolRating, 5 stars4 weeks ago
This condo was amazing loved waking up to the beautiful ocean view and when you came out the door you had the also beautiful bay view I had a lot of questions and Julie got right back to me every time I would definitely recommend booking this stunning condo and my sisters and I will be booking again in the future ❤️😊
Top Guest favourite
Condo in Ocean City
5 out of 5 average rating, 28 reviews

Direct Oceanfront with Pool - Steps To The Beach

KierstonRating, 5 stars1 week ago
We had a wonderful time! Waking up both mornings to dolphins right outside your sliding glass door was the highlight! We can’t wait to get back!

Pet-friendly condo rentals

Guest favourite
Condo in Dewey Beach
4.96 out of 5 average rating, 135 reviews

Luxury water-view condo with high-end finishes

AndreaRating, 5 stars3 weeks ago
The apartment is beautiful, very comfortable, and fully equipped with everything you need for a great beach vacation. We had a lovely stay and really enjoyed the space.
Superhost
Condo in Ocean City
4.82 out of 5 average rating, 76 reviews

𝙂𝙪𝙚𝙨𝙩 𝙛𝙖𝙫𝙤𝙧𝙞𝙩𝙚 Lovely 2lvl Condo Steps 2Beach+Pool

KristenRating, 5 stars3 weeks ago
Great space for a couple and clean! The location was fantastic -- walkable to some great restaurants, to get coffee in the morning, and to CVS in case you forgot something. Also, close enough that you can do about a 20 minute drive to the inlet and boardwalk. Would definitely stay here again!
Top Guest favourite
Condo in Ocean View
5 out of 5 average rating, 79 reviews

Bethany Bay. Sleeps 4. AC, Pool, Ground Floor

ShraddhaRating, 5 stars1 week ago
Stephanie’s place was immaculate, thoughtful and greatly decorated! All instructions were clear and there were amenities like cooler, beach towels and beach chairs, that were very useful for us. The area is very quiet and serene and we loved the stay!
Guest favourite
Condo in Dewey Beach
4.88 out of 5 average rating, 196 reviews

Read Ave Dewey Condo - Bay Front, Private Beach

AngelinaRating, 5 stars2 weeks ago
Very nice and easy check in and check out.
Top Guest favourite
Condo in Rehoboth Beach
4.95 out of 5 average rating, 112 reviews

Beach Perfect Getaway: 2-Bedroom Apartment

SharathRating, 5 stars2 weeks ago
Great location, close to Rehoboth Beach and good access to stores and restaurants. House was exactly as described, would recommend.
Top Guest favourite
Condo in Montego Bay
5 out of 5 average rating, 77 reviews

Beautiful waterview 2B condo w/Dock&Close to Beach

MatthewRating, 5 stars4 weeks ago
Absolutely perfect stay! The place was spotless, stylish, and exactly as described—if not better. It’s ideal for anyone traveling with pets or children—there was plenty of space, a safe and secure environment, and thoughtful touches that made everyone feel welcome (including our furry friend!). Our host, Erika, was incredibly responsive and thoughtful, making check-in a breeze. The location was perfect—close to everything we needed, but still peaceful and relaxing. I couldn’t have asked for a better experience and would 100% stay here again. Highly recommend!
Guest favourite
Condo in Dewey Beach
4.85 out of 5 average rating, 198 reviews

On the Bay, Private Beach-Boat Slip

JohnRating, 5 stars1 month ago
Catherine's place was great for our family and young son. The location is tremendous and there are great views just eating breakfast and sipping morning coffee. The place itself is well stocked and has a very efficient layout (pocket doors) for the space. Catherine was super responsive and understanding, we really enjoyed our stay.
Top Guest favourite
Condo in Dewey Beach
4.97 out of 5 average rating, 262 reviews

Sweet getaway - beach block, steps from the beach!

HannahRating, 5 stars3 weeks ago
We had a great stay and loved the short walk to the beach! Brian communicated very well and accommodated an early and late check in for us! Would stay here again.

Condo rentals with a pool

Superhost
Condo in Ocean City
4.79 out of 5 average rating, 19 reviews

Updated Studio,Steps to Beach,Pool

HeatherRating, 5 stars1 week ago
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!
Top Guest favourite
Condo in North Ocean City
5 out of 5 average rating, 31 reviews

Amazing Bayside Views @Sunset309

NealRating, 5 stars3 months ago
Our stay was great... St Patty's weekend. there was alot to do and Chad was very responsive. the atmosphere was wonderful. a much needed break will recommend and book again.
Superhost
Condo in Ocean City
4.94 out of 5 average rating, 17 reviews

Luxury 2BD Condo, Walk to Beach, Pool&Tennis Court

KaranvirRating, 5 stars8 months ago
Vladimir has a great airbnb for the price. within 15 minutes of the boardwalk. The airbnb itself has a very modern design with a nice view.
Top Guest favourite
Condo in North Ocean City
5 out of 5 average rating, 44 reviews

Top Rated! Beautful Sunsets! Midtown Bayside Condo

Maria CarmenRating, 5 stars2 weeks ago
Muy acogedor el lugar limpio ,organizado la anfitriona siempre muy atenta y pendiente a mí como huéspedes el lugar muy tranquilo y el parqueo excelente gracias ☺️ se lo recomiendo a ojos cerrados
Guest favourite
Condo in Ocean City
4.91 out of 5 average rating, 35 reviews

Cozy 1 BR Condo - 5 Minute walk to Beach, w/ Pool!

DanielleRating, 5 stars2 weeks ago
Our stay was very peaceful and relaxing all thanks to Clint’s place! We were able to walk to the boardwalk and restaurants. The place itself was clean and has everything you would need on vacation. Thank you Clint!
Top Guest favourite
Condo in Montego Bay
4.95 out of 5 average rating, 21 reviews

The Coastal Condo

ChelsieRating, 5 stars5 days ago
We loved our stay at The Marylander in Colleen & Joe’s condo. From the very start she was very responsive, understanding and kind. The condo was the perfect amount of space which was well cared for & clean, we enjoyed the amenities that came with the building and the short walk to the beach! I’m already looking forward to booking another stay here!
Superhost
Condo in Ocean City
4.88 out of 5 average rating, 196 reviews

🌊Oceanfront studio w/ amazing views & amenities🏖

LawrenRating, 5 stars3 weeks ago
Lisa’s place was awesome and exactly how she described it! We loved waking up to the sounds of the ocean and the beautiful views of the bay and ocean. Everything you need is in this condo!!! Thanks again Lisa!!!
Guest favourite
Condo in Ocean City
4.77 out of 5 average rating, 66 reviews

Recently Remodeled Two Bedroom, One Bath Condo

JermaineRating, 5 stars1 month ago
Shelley was a great host, this space was beautiful and modern, very clean, we felt right at home and had everything he needed. Very spacious with modern washer and dryer, 5 min drive from the boardwalk. Area was very peaceful and although the pool wasn’t open when we booked, it was a deep pool I would’ve liked to use. Maybe next time . Would recommended to anyone.

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