Ocean Pines vacation rentals

We found 7,147 vacation rentals — enter your dates for availability

September 2023

SSunday	MMonday	TTuesday	WWednesday	TThursday	FFriday	SSaturday




		26

October 2023

SSunday	MMonday	TTuesday	WWednesday	TThursday	FFriday	SSaturday

Select from 214 homes, 17 cottages, and other vacation rentals in Ocean Pines to find one that's perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll have the amenities you expect and more, which might include parking and a pool. Whatever you're looking for, you're sure to find a rental for everyone's needs, including accessible or non-smoking choices.

Find spaces that suit your style

Find the best place to stay - Ocean Pines

Large estate & cottage with private pool, firepits, & game room

8 bedrooms · 5+ bathrooms

Beautifully renovated bayfront home with deck, game room, fireplace & EV charger

Sleeps 13 · 6 bedrooms · 4 bathrooms

One Level Waterfront Home-Pet Friendly - 5 Pools- Golf-Sleeps 8- Self Check-In !

3 bedrooms · 2 bathrooms

Top rated rentals - Ocean Pines

The Chalet

Wonderful quaint house, very clean & comfortable. Great communication with the Host regarding arrangements

Lindsey T.

Stayed Sep 2023

Coastal Ambience

This was a wonderful, clean, well stocked home. Decor was beautiful, area was cozy, quaint and quiet. Can’t say enough good things about this home…..and so close to ocean city and all of the action/restaurants. As repeat visitors to Ocean Pines area we can definitely say this is an amazing area to vacation and this was a lovely house with a very attentive property host. Kathy was super fast to help or answer any questions we might have had. 5 stars all the way!

Victoria T.

Stayed Sep 2023

Image of 3 Bedroom 2 Bath Beach House/ Ocean City, MD/Ocean pines MD

Labor Day

We had a wonderful time, your home is very lovey. The master bed was sooo comfortable! We enjoyed the screened in porch. There was only one roll of toilet paper for 2 bathrooms. Overall, great location, quiet neighborhood. We will visit again.

Jenifer H.

Stayed Sep 2023

Honey blue was AMAZING

It was six adults and two children at the age of 10 years old. It was fully stocked very roomy. We majority of the time stayed on the screen and easy access to the beach even on Labor Day weekend!!! Will definitely be booking here again 😁 I recommend this to EVERYONE. Very kid friendly too.

Ashley W.

Stayed Sep 2023

Lovely place ♥️

Great price, friendly homeowner, good neighborhood, and not a far drive to ocean city! Me and my family loved it here and can’t wait to stay again! Would definitely recommend 😊

Tina G.

Stayed Aug 2023

Perfect location and house

I booked this house for my brother's bachelor and it lived up to the hype. The location of the house offers a private spot while being close enough to golf courses and all the attractions Ocean City has to offer. The house has plenty of space and beds to accommodate for larger groups, and it couldn't not have been a smoother process checking in and out.

Jeff G.

Stayed Aug 2023

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
All the privacy of home
Enjoy full kitchens, laundry, pools, yards and more
More for less
More space, more privacy, more amenities — more value
A place for everyone
We stand for diversity, inclusion and families everywhere.
Learn more