Ocean Pines vacation rentals
Book unique homes, vacation rentals, and more on Airbnb
Top-rated vacation rentals in Ocean Pines
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Ocean Pines vacation rentals
Other great vacation rentals in Ocean Pines
Condo in Ocean City
4.84 out of 5 average rating, 144 reviewsUnit 2 on 41 St Ocean Side, Only 50 steps to beach
Condo in Ocean City
4.99 out of 5 average rating, 176 reviewsDirect Oceanfront close to Northside Park!
Condo in Ocean City
4.91 out of 5 average rating, 259 reviewsOcean Front 802 Midtown Oasis Pool & Parking
Guest suite in Ocean City
4.98 out of 5 average rating, 273 reviewsSpacious Luxury Studio in Ocean City
Condo in Ocean City
4.82 out of 5 average rating, 125 reviews1 BR Ocean Block (Unit 17) 40th St Midtown OC
Condo in Ocean City
4.89 out of 5 average rating, 152 reviewsPrime Condo North OC 2 Blocks to Beach w/ Pool
Townhouse in Ocean City
4.95 out of 5 average rating, 104 reviewsIslandCoveParadise: Luxury-NewlyBuilt/Brdwalk/Pool
Condo in Ocean City
4.86 out of 5 average rating, 104 reviews2 Bdrm Oceanfront-Pool, Xbox, Pickleball, Gym, HBO
Ocean Pines condo rentals
Condo in Berlin
4.98 out of 5 average rating, 103 reviewsAmazing Waterfront in Berlin, MD- Sea Breeze Suite
Condo in Bethany Beach
4.93 out of 5 average rating, 280 reviewsSea Colony Premier Family Resort
Condo in Ocean City
4.9 out of 5 average rating, 250 reviews101 Bimini Stunning Renovations Direct Ocean Front
Condo in Ocean City
4.99 out of 5 average rating, 204 reviewsSteps to the Beach, Ocean View 1BR, Renovated
Condo in Ocean City
4.83 out of 5 average rating, 139 reviewsRomantic Beach Inscape-Best Ocean View+Heated Pool
Condo in Ocean City
4.85 out of 5 average rating, 100 reviewsWater Front Condo w/Pool Short Walk to Beach
Condo in Ocean City
4.93 out of 5 average rating, 256 reviewsCANAL FRONT Wi-Fi, Roku streaming, Netflix
Condo in Ocean City
4.95 out of 5 average rating, 22 reviewsThe Sea Voyage Canal Front 1 Bedroom Balcony (215)
Ocean Pines house rentals
Home in Ocean View
4.92 out of 5 average rating, 530 reviewsTiny House at Good Earth, near Bethany Beach
Home in Ocean Pines
4.8 out of 5 average rating, 121 reviews122 Ocean Parkway, Ocean Pines, MD
Home in Berlin
4.78 out of 5 average rating, 174 reviewsOC, Md great amenities in community, near beaches
Home in Ocean View
4.87 out of 5 average rating, 447 reviewsPrivate place near Bethany Beach
Home in Ocean Pines
4.87 out of 5 average rating, 116 reviewsTortuga Cottage: Your All- Season Getaway
Home in Ocean Pines
4.9 out of 5 average rating, 134 reviewsWaterfront Beach Home in the Ocean City, MD Area
Home in Ocean City
4.97 out of 5 average rating, 121 reviewsPet Friendly SFH w/ fenced yard, 2blocks to BEACH!
Home in Ocean City
4.94 out of 5 average rating, 221 reviewsMad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB
Quick stats about vacation rentals in Ocean Pines
Total rentals
260 properties
Rentals with a pool
140 properties have a pool
Pet-friendly rentals
80 properties allow pets
Family-friendly rentals
240 properties are a good fit for families
Total number of reviews
6.5K reviews
Nightly prices starting at
$40 before taxes and fees
Your guide to Ocean Pines
All About Ocean Pines
What started in 1968 as a small resort on Maryland’s Easter Shore has grown into a thriving seaside community with swimming pools, walking trails, a yacht club, and a marina ripe for stand-up paddleboarding, kayaking, and canoeing. Ocean Pines is home to a network of canals that offer direct access to the water for some residents.
At nearby Ocean City, just five miles away, you can stroll the boardwalk or go for a swim along the 10 miles of beaches. Amusement parks offer thrill rides and arcade games, and you can head over to Ocean City Life-Saving Station Museum to learn about the historic role performed by the United States Life-Saving Service. Ocean Pines is also less than 30 minutes away from the stunning Assateague Island, a National Natural Landmark known for its pristine landscapes and wildlife, including white-tailed deer, river otters, and muskrats.
The best time to stay in a vacation rental in Ocean Pines
The Ocean City area is an extremely popular summer destination thanks to the beautiful weather and sandy beaches. Accommodation options may be limited during this time so it is a good idea to book early. Fall and spring tend to be much quieter, and you may find that many of the amenities in Ocean Pines are largely empty on weekdays, as well as the Ocean City Boardwalk and beaches. Ocean City holds its annual Sunfest at the end of September, offering activities like arts and crafts as well as a variety of food.
During the winter, it gets very quiet in Ocean Pines, and many local businesses close for the season. However, this is still a great time to book an Ocean Pines rental as you can explore the nearby beaches and parks in solitude. There is also a farmer’s market held every Saturday to stock up on fresh produce and artisanal products. There are even themed markets for Halloween, Thanksgiving, and Christmas.
Top things to do in Ocean Pines
Assawoman Bay
Twenty minutes outside of town, Assawoman Bay is a lagoon located on the northern end of Baltimore. It is a popular destination for many water activities, including boating and fishing. The most popular catches here are summer flounder, bluefish, and Atlantic stingray.
Ocean City
Located just a short drive from Ocean Pines, Ocean City offers all the bustling activities and attractions of a large resort city. Here, you can visit one of the many amusement parks such as Jolly Roger, watch the sunset on the boardwalk, or grab crab cakes and drinks at one of the local bars and restaurants.
Assateague Island
This gorgeous uninhabited island stretched between Virginia and Maryland offers some of the area’s most pristine beaches and natural landscapes, including salt marshes and maritime forests surrounding the island’s stunning bays. It is a great spot for hiking and wildlife viewing and while you are there, you may even be able to see the island’s wild ponies.
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Ocean Pines?
Yes! Work meets play with ease at over 140 vacation rentals in Ocean Pines featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Ocean Pines?
Four-legged friends are welcome in Ocean Pines. Choose from more than 80 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Ocean Pines?
Experience the best of Ocean Pines with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there Ocean Pines house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 110 house rentals with pools in Ocean Pines, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Ocean Pines have a bbq area?
Absolutely! We offer over 80 house rentals with a bbq area in Ocean Pines. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Ocean Pines have a gym?
Absolutely! We offer over 10 house rentals with a gym in Ocean Pines. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Ocean Pines have self check-in?
Absolutely! We offer over 90 house rentals with self check-in in Ocean Pines. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Ocean Pines?
Ocean Pines has more than 210 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Destinations to explore
- Baltimore Vacation rentals
- Ocean City Vacation rentals
- Atlantic City Vacation rentals
- Cape May Vacation rentals
- Wildwood Vacation rentals
- Rehoboth Beach Vacation rentals
- Washington Vacation rentals
- Deep Creek Lake Vacation rentals
- Philadelphia Vacation rentals
- New York Vacation rentals
- Jersey City Vacation rentals
- The Hamptons Vacation rentals
- Rentals with outdoor seating Ocean Pines
- Kid-friendly rentals Ocean Pines
- Rentals with a washer and dryer Ocean Pines
- Rentals with pools Ocean Pines
- Fitness-friendly rentals Ocean Pines
- Rentals with a fire pit Ocean Pines
- Rentals with beach access Ocean Pines
- Family-friendly rentals Ocean Pines
- Monthly Rentals Ocean Pines
- Rentals with a patio Ocean Pines
- House rentals Ocean Pines
- Pet-friendly rentals Ocean Pines
- Waterfront rentals Ocean Pines
- Rentals with a fireplace Ocean Pines
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes