Beach house holiday rentals in Ocean Pines

Find and book unique beach houses on Airbnb

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Popular amenities for Ocean Pines beach house rentals

Beachfront house rentals

Superhost
Home in Ocean City
4.67 out of 5 average rating, 6 reviews

Oceanfront Condo with Pool on 68th St - 1F

Karsten FayeRating, 5 stars1 week ago
My husband and I were very happy with our stay at John's. It had everything we needed. It was tidy, clean, and peaceful. Just what we were looking for. His response time for anything we needed or any question we had was awesome.
Guest favourite
Home in Ocean City
4.95 out of 5 average rating, 19 reviews

Spacious Home w/ Parking Steps to Beach Boardwalk.

RehanaRating, 5 stars1 month ago
Absolutely superb location if you're looking for beach/boardwalk access. The layout - three seperate floors, two with seperate entrances - was perfect for our group of 4 families with lots of different nap schedules. Porches were definitely a plus (for adults and kids to run around). There were lots of dishes available to us/plenty of supplies for our stay. Would stay again!
Top guest favourite
Home in Ocean City
5 out of 5 average rating, 37 reviews

New waterfront home on bay, quick walk to beach

AaishahRating, 5 stars3 weeks ago
John was an exceptional host. He was very responsive. The house was on the water & had a beautiful outdoor space. The home is in pristine condition & extremely clean. It appeared newly renovated. It has a beautiful coastal motif & looked like it had been professionally decorated. It was well equipped & I didn’t have to use my own housewares as I normally bring to an Airbnb i.e. pots, pans, dishes, cutlery. Also, these items were high end & looked like the items the owner would use. I would highly recommend. I loved the outdoor shower, especially for kids, to rinse off sand after the beach.
Guest favourite
Home in Ocean Pines
4.95 out of 5 average rating, 22 reviews

Robin Hood Retreat

DanyetRating, 5 stars3 weeks ago
Bill is a wonderful , polite. ,accurate and a cool host. The house was neat and clean. Bill made sure you have fresh linens for each bedroom. He was easy to get in contact with.Bill makes you feel at home.The house is beautiful and in a peaceful area!( The pictures does not do this house any justice) Bills house is safe and secure. Bill has many properties and I will be booking again. Thanks bill for everything. You are great!!
Superhost
Home in Montego Bay
5 out of 5 average rating, 4 reviews

Family Townhouse, Rooftop Jacuzzi, Walk to Beach

CaitlinRating, 5 stars11 months ago
Overall we loved our stay. Check-in was easy and went off without a hitch. The house was perfect for our family and exactly as described and pictured. It was very neat and clean. The large kitchen was well stocked with all items that we needed and the mutliple fridges were very useful! The proximity to the beach was a huge plus. Very nice, quiet location at the top of Ocean City away from the hustle and bustle but still with many walkable stores, restaurants and entertainment options. Very great find.
Superhost
Home in North Ocean City
4.71 out of 5 average rating, 7 reviews

Memories to last a lifetime Free linens & Towels

AllisonRating, 5 stars8 months ago
Our weekend stay was above our expectations! John and Jennifer allowed us to do early check in, Jennifer met us at the house to give us the keys and to answer all of our questions. The listing describes the house perfectly and the pictures are exactly what the house looks like. The location is right off of the beach, but is conveniently located within walking distance to a ton of places. The house was spotless, the sheets and towels were newer, and the provided kitchen utensils and pans were in great shape! We can not wait to stay with John and Jennifer again!
Guest favourite
Home in Ocean City
4.93 out of 5 average rating, 27 reviews

Waterfront Oasis

KateRating, 5 stars7 months ago
So grateful to Tierney for all she did to make this Airbnb experience one of our best ones yet. Truly one of the best hosts we’ve ever had! It was our wedding weekend! She was so accommodating and her home so welcoming. Highly recommend! she also bought a giant mirror for us to get ready with! Best host ever!
Top guest favourite
Home in Ocean Pines
4.99 out of 5 average rating, 87 reviews

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines

MiaRating, 5 stars4 days ago
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!

Beach house rentals with a pool

Top guest favourite
Home in Ocean City
5 out of 5 average rating, 15 reviews

Brand New Luxury 4BR Home w Pool & Steps to Ocean

MickeyRating, 5 stars1 month ago
Beautiful condo! Went for a boys golf trip. The kitchen and living room area was perfect for all 8 of us to hangout at night and watch sports. Only down side was you had to rent linens and bath towels but was clearly communicated once you booked. Would 100% stay there again
Guest favourite
Home in Montego Bay
4.97 out of 5 average rating, 95 reviews

Beach Oasis w/ King Suite + Outdoor Shower & Pool

NatalieRating, 5 stars3 days ago
It was a great stay!! The house is beautiful and a great location! There is lots to do near by and close to the beach! Definitely would stay again!
Top guest favourite
Home in Berlin
4.94 out of 5 average rating, 36 reviews

Luxury Townhome WestOC -4 BRS / golf / asssateague

AsiaRating, 5 stars1 day ago
This was perfect for my family. The Townhouse was spacious, and we loved the balconies. The location was great and the host was very responsive. I definitely recommend this place, and plan to stay again in the future.
Top guest favourite
Home in Rehoboth Beach
5 out of 5 average rating, 195 reviews

Beautiful Beach House in Rehoboth

RebeccaRating, 5 stars2 weeks ago
Had the absolute best time staying at this gem. The house is stunning and Autumn was a fantastic host! The house is spacious and open. It was exactly as described but better. We couldn’t have been happier. Will definitely be back!
Top guest favourite
Home in Bethany Beach
5 out of 5 average rating, 33 reviews

Coastal Cottage! Walk to Beach!

JosephRating, 5 stars3 days ago
My family and I had an amazing time at the Coastal Cottage! Between the awesome sound system and the heated pool, we almost didn’t want to leave the house to check out the local bars and restaurants! Steve is an incredible host. Super friendly and made the whole check in and check out process very easy. The only thing I wish were different is that we booked a couple more days! I highly recommend this place and know for certain that we will be looking at the available dates for our future trips back to Bethany Beach!
Top guest favourite
Home in Montego Bay
4.97 out of 5 average rating, 115 reviews

Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.

KimberlyRating, 5 stars1 week ago
Tammy’s place was a beautiful Airbnb that provided me and my friends a wonderful experience we loved how private and reserved the neighborhood is we also loved all the accommodations such as the walking distance to the pool and beaches.I would definitely visit here again.
Guest favourite
Home in Montego Bay
4.9 out of 5 average rating, 126 reviews

Beautiful Cottage W/ shared pool & close 2 beach

TerryRating, 5 stars2 weeks ago
Everything was as described. Jennifer was very responsive and left excellent instructions on everything. We will stay there again.
Guest favourite
Home in Montego Bay
5 out of 5 average rating, 13 reviews

Charming Condo with pool and 2 bedrooms

AshleyRating, 5 stars3 weeks ago
Our stay was wonderful. Beach and many restaurants/bars within walking distance. The host was extremely accommodating, kindly offering us the flexibility to check in a day early and check out late—an option we ultimately didn’t use, but greatly appreciated. The property was clean, comfortable, and exactly as described. I would gladly choose to stay here again.

Private beach house rentals

Guest favourite
Home in Ocean City
5 out of 5 average rating, 7 reviews

Waterfront 4BR Home with pier amazing views

LizRating, 5 stars9 months ago
We had such an incredible stay! True Beach Bliss without a doubt! The home was beautiful and did not miss a touch. Great location and we felt right at home. Best time ever and we truly had a fabulous time. Shoutout to the maintenance person who went above & beyond helping us to fix the elevator as well as even edited and helped me to unload my car to ensure we got in the elevator safe and sound. Wished we had more time and will be back again. 🏖️😊
Guest favourite
Home in Montego Bay
5 out of 5 average rating, 15 reviews

Turtle Cove

NathanRating, 5 stars1 month ago
We had a great stay at Matthew's place in OCMD. The house was very conveniently located - only a few short block walk to the beach or a variety of restaurants, shops, and amusements (mini golf, etc.). There was a dedicated parking spot and ample street parking as well. The house worked great for our weekend trip, as two couples plus two small children. Matthew was extremely responsive, making the entire process very easy!
Guest favourite
Home in Ocean City
4.82 out of 5 average rating, 17 reviews

Rooftop deck, fire pit, beach cart, BBQ

Gerson CruzRating, 5 stars3 weeks ago
The place was clean organized and has everything that you will need to have a good time at Ocean City It’s a great and quiet location I was surprised that they take the time to have everything ready for us even beach, chairs, and coolers the rooftop deck was amazing
Top guest favourite
Home in Bethany Beach
5 out of 5 average rating, 11 reviews

3BR House with pool -short walk to beach and town!

ClaireRating, 5 stars8 months ago
Amy’s friendly and welcoming beach house was the perfect after Labor Day getaway. The kitchen was well stocked with essentials for family meals. The beds were comfortable, and I especially appreciated closets and drawers in all three bedrooms. Plenty of beach chairs and wagon available so no need to bring them . The local Bethany Beach was within walking distance, though after the summer season we found easy parking one block from the water. Great price for a long weekend near the beach after the summer season. Amy was attentive and available. We had no issues at all, and would eagerly book a long weekend again at Amy’s home.
Guest favourite
Home in Ocean City
4.95 out of 5 average rating, 21 reviews

Beach, Boardwalk, and Fun Times

TammyRating, 5 stars1 month ago
In all honesty, when I first pulled up I thought “ what?!” But, they have redone the inside, Nicely. Very comfortable, clean. I felt safe. We had the things we needed. You can’t see the ocean because of the big hotel but you can hear and feel it. He had things to use at the beach, which was very nice. The boardwalk is a good walk but was doable. This is a good place to stay.
Top guest favourite
Home in Lewes
4.99 out of 5 average rating, 100 reviews

Willow Oak Waterview Cottage

MarissaRating, 5 stars1 week ago
Beautiful little cottage on the water… would definitely stay again.
Guest favourite
Home in Ocean City
4.93 out of 5 average rating, 76 reviews

Waterfront Oasis

JenniferRating, 5 stars2 weeks ago
Megan’s place was absolutely perfect! We loved everything about our stay. Megan was extremely communicative and made sure everything was perfect. The view is unmatched (and the photos don’t do it justice!). We’ve been coming to OCMD since I was a kid and this place is number one in my book. Can’t wait to stay again!
Superhost
Home in Ocean City
5 out of 5 average rating, 4 reviews

The Tower

Jesse Rating, 5 stars1 month ago
Very nice house with a lot of space for a larger group. Kevin was accommodating & was very considerate when we let him know we would have our service dog with us. Multiple bathrooms throughout the house & the entertainment living room was a nice area for the group.

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