Ocean Pines vacation rentals near the ocean
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Top-rated vacation rentals in Ocean Pines
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Popular amenities for Ocean Pines vacation rentals
Other great vacation rentals in Ocean Pines
Barn in Selbyville
5.0 out of 5 average rating, 147 reviewsRanch Stay- Farm Animals, Jacuzzi, Arcade, Beaches
Dec 19 – 26
Guest suite in Dagsboro
4.98 out of 5 average rating, 213 reviewsHome away from home in law suite
Sep 22 – 27
Home in Ocean Pines
5.0 out of 5 average rating, 100 reviewsCharming Waterfront Cottage w/2 King Suites + Dock
Jun 8 – 15
Condo in Ocean City
4.99 out of 5 average rating, 173 reviewsDirect Oceanfront close to Northside Park!
Mar 9 – 16
Condo in Berlin
4.98 out of 5 average rating, 103 reviewsAmazing Waterfront in Berlin, MD- Sea Breeze Suite
Sep 16 – 23
Condo in Ocean City
4.88 out of 5 average rating, 105 reviewsUnit 11 on 41 St Ocean Side 50 steps to beach
Oct 13 – 20
Condo in Ocean City
5.0 out of 5 average rating, 127 reviewsThe Search For Surf-Ocean Block Sleeps 4
Apr 21 – 28
Condo in Ocean City
4.9 out of 5 average rating, 176 reviews**Beautiful newly renovated OC MD water view home*
May 2 – 9
Ocean Pines house rentals
Home in Ocean View
4.87 out of 5 average rating, 445 reviewsPrivate place near Bethany Beach
Dec 14 – 21
Home in Selbyville
4.89 out of 5 average rating, 160 reviewsCountry Private Vacation House
May 6 – 13
Home in Ocean City
4.97 out of 5 average rating, 117 reviewsPet Friendly SFH w/ fenced yard, 2blocks to BEACH!
Feb 27 – Mar 6
Home in Ocean City
4.85 out of 5 average rating, 158 reviewsBeach Paradise IV-Downtown Luxury Condo Bay View
Nov 17 – 24
Home in Ocean Pines
4.88 out of 5 average rating, 101 reviewsCozy home minutes from beach, outlets & casino
Jan 31 – Feb 7
Home in Ocean Pines
5.0 out of 5 average rating, 12 reviewsOcean Pines MD Shady Rest Getaway
Nov 1 – 8
Home in Ocean Pines
5.0 out of 5 average rating, 20 reviewsThe Admiral's Cottage
Mar 1 – 8
Home in Ocean Pines
4.82 out of 5 average rating, 62 reviewsHome Away from Home , Pet friendly retreat
Oct 18 – 25
Ocean Pines condo rentals
Condo in Ocean City
4.89 out of 5 average rating, 164 reviews🌊Oceanfront studio w/ amazing views & amenities🏖
Nov 16 – 23
Condo in Ocean City
4.91 out of 5 average rating, 722 reviewsLight and Airy Oceanfront Condo w/ Private Balcony
Oct 7 – 14
Condo in Ocean City
4.99 out of 5 average rating, 179 reviewsCozy oceanfront condo with stunning ocean views
Oct 11 – 18
Condo in Ocean City
4.82 out of 5 average rating, 136 reviewsRomantic Beach Inscape-Best Ocean View+Heated Pool
Nov 29 – Dec 6
Condo in Ocean City
4.87 out of 5 average rating, 165 reviewsBayside Retreat in the Heart of Ocean City!
Oct 11 – 18
Condo in Ocean City
4.91 out of 5 average rating, 254 reviewsOcean Front 802 Midtown Oasis Pool & Parking
Mar 24 – 31
Condo in Ocean City
4.99 out of 5 average rating, 106 reviewsCozy & Clean Condo on 36th st. Steps to Beach!
Oct 19 – 26
Condo in Ocean City
4.92 out of 5 average rating, 117 reviewsBeach Baby Ocean Block Studio-Mid Town-All U Need
Nov 18 – 25
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
G$8,360 GYD 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.
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 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!
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.
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