
Waterfront vacation rentals in Ocean Pines
Find and book unique waterfront rentals on Airbnb
Quick stats about waterfront rentals in Ocean Pines

Total vacation rentals
Explore 70 vacation rentals in Ocean Pines

Nightly prices starting at
Ocean Pines vacation rentals start at G$16,729 GYD per night before taxes and fees

Verified guest reviews
Over 1,830 verified reviews to help you choose

Family-friendly vacation rentals
70 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
70 of Ocean Pines vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Ocean Pines rentals

4.8 Average rating
Ocean Pines stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated waterfront rentals in Ocean Pines
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB
After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!

Gorgeous Beachfront! King Bed, Direct Ocean View!
Stunning beachfront condo with direct view of the ocean! Your vacation home away from home! Everything you need right ON the beach. All linens, supplies and a well-stocked kitchen! New 65" TV w/free 4K Netflix provided! Modern serene decor in the heart of OC! Feel like getting out? Enjoy walking distance to Seacrets, Mackey's, and Fager's Island, Subway, Candy Kitchen or Dumsers' Dairyland! More adventure? Walk to minigolf, pontoon boats and jetski rentals! Only 4 minute drive to the boardwalk!!

2BRCapri: Indoor Pool, Game Room, Massage Chair
ALL THE COMFORTS OF HOME AT THE BEACH! BRAND NEW RENOVATED BATHROOMS! -ALL LINENS INCLUDED -Comfortable electric-reclining sofas -65-in smart Roku TV with soundbar. -Massage chair in master bedroom -Balcony & Dining Area w/ Ocean +Bay Views -In-unit W/D -Many conventional & USB Outlets -Arcade level features b-ball hoop, pool tables, ping-pong, shuffleboard, air-hockey -Outdoor tennis court -Large heated indoor pools -can swim full laps -Sauna and Gym -Board games in unit -Fast Wifi

Stunning private waterfront suite
Welcome to your cozy getaway with stunning water views from every room! This sweet 2-bedroom, 1-bath suite boasts a private entrance, a living room, and a cute kitchenette. Nestled in a peaceful, family-friendly neighborhood, you'll have year-round access to swimming pools, a golf course, tennis courts, a Yacht club, and lovely parks nearby. Only a quick 10-minute drive lands you on the sandy beaches and lively Boardwalk of Ocean City. Park in the driveway and step into your own private escape!

Water view at Ocean Pines Yacht Club Condo
Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

Luxury Oceanfront Escape!
This unique place has a style of its own. Wake up, pour your cup of coffee, and watch the sunrise from your direct oceanfront balcony. The beach is a few short steps away. Walking distance to many restaurants and shops! This recently renovated one bedroom condo features an outdoor shower, an elevator, fully equipped kitchen, a library of books, 1.5 bathrooms, Wi-Fi, large screen smart tv, bedroom tv, parking spot, washer/dryer and so much more! Fresh linens, towels, and toiletries included.

Edgewater Escape - Luxury Bayfront Loft with Porch
You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

Waterfront Beach Home in the Ocean City, MD Area
There is room for 8 adults (plus 2 kids). Located in the premiere seaside community in the Ocean City area, Ocean Pines, this wonderful waterfront home provides amazing views both day and night. The open floor plan provides guests with lots of room to socialize and bond, but also has secluded bedrooms that provides needed privacy. The outdoor living area is to die for. Sit back and watch the sun set over the canal while you catch up with friends or loved one. Use our bikes!

Birdies by the Bay | Waterfront & Private Dock
Welcome to Birdies by the Bay! This newly remodeled 3-bedroom, 2-bath waterfront home sleeps 6 people. Enjoy an open layout, a sunny water-view room, and a deck with seating, a grill, and a private dock overlooking the 3rd Green of the golf course. Nearly everything’s new—just the stall showers kept their charm. Perfect for families, couples, or small group getaways in beautiful Ocean Pines!**** Must be 25 years or older to reserve this property. Please See rules.****

Coastal Retreat near the beach
Kick back and relax in this calm, stylish space just 15 minutes from Ocean City MD beaches. The unit has marsh and water views of Assawoman Bay/Manklin Creek. Located across the bay from Ocean City , MD you are close to the action but can retreat back to a quiet sanctuary when you are looking for some relaxation away from the beach crowds. If you like nature, frequent visitors include, deer, fox, blue heron, egrets, bald eagles, owls and many other birds.

Quiet setting on private pond among the wildlife
Enjoy a quiet, private setting just 3 miles from the Bethany Beach boardwalk. Nestled across from the Assawoman Wildlife Refuge, you can relax in a spacious home away from home. Plenty of room for the kids to play outside while you relax on the dock overlooking the pond. Guests have access to the second floor of the home which includes a full size kitchen, 3 bedrooms and living room that all have Smart TVs. Plenty of parking for you and guests.

Secluded Waterfront - Beach 15mi, Kayaks, Firepit
Casa Blue Heron is a 2,254 ft² (209 m²) custom waterfront home with a private dock, firepit, and water views throughout - nestled on a tidal inlet connected to Chincoteague Bay - and near Assateague, Berlin, Ocean City, Snow Hill, and much more. ★ "A private and tranquil setting where it is impossible not to relax and appreciate nature… Wish I had booked an extra day!" Add us to your wish list by clicking the ❤️ in the upper-right corner.
Popular amenities for Ocean Pines waterfront rentals
Waterfront apartment rentals

Oceanfront Renovated Condo with Indoor Pool! MB308

Bayside Bungalow - Waterfront

Water Front Apartment

Pelican Beach-Oceanfront

Ocean City Beach Retreat with Linens Included

Bayfront Escape w/Stunning Sunsets & Private Dock

Amazing oceanfront view 3 blocks from boardwalk

Ocean Paradise
Waterfront house rentals

Waterfront Vacation Home in Ocean Pines

Ocean Pines, Waterfront Oasis

Villa Caribbean OCMD

Fabulous Waterfront Getaway with Sunsets & Eagles

Manklin Creek Retreat | Water Views + Boat Dock

Waterfront 3BR | Private Dock + Views

Closest condo to the beach in OC! Dog Friendly!

Ocean Pines-OCMD Bliss at the Beach- Sat. to Sat.
Waterfront condo rentals

One Bedroom Beachfront Apartment Mid-Town

Direct Ocean Front! Unwind with an Ocean View

Summer Palace in Ocean city .

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

Bayside Retreat in the Heart of Ocean City!

Direct Oceanfront close to Northside Park!

The Hideaway By The Bay OCMD

Direct Oceanfront with a View and Amenities Galore
When is the best time to visit Ocean Pines?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$51,861 GYD | G$41,823 GYD | G$39,523 GYD | G$46,424 GYD | G$52,070 GYD | G$74,445 GYD | G$78,209 GYD | G$73,609 GYD | G$63,362 GYD | G$54,161 GYD | G$49,560 GYD | G$49,979 GYD |
| Avg. temp | 3°C | 4°C | 7°C | 13°C | 18°C | 23°C | 26°C | 24°C | 21°C | 15°C | 9°C | 5°C |
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- Chincoteague Island
- Cape May Beach NJ
- Assateague Island National Seashore
- Ocean City Beach
- Wildwood Crest Beach New Jersey
- Ocean City Boardwalk
- Broadkill Beach
- Rehoboth Beach
- Assateague State Park
- Cape Henlopen State Park
- Bethany Beach Boardwalk
- Willow Creek Winery & Farm
- Northside Park
- Delaware Seashore State Park
- Jolly Roger Amusement Park
- Fenwick Island State Park Beach
- Ocean City Boardwalk
- Wildwood Boardwalk
- Roland E Powell Convention Center
- Ocean Pines Golf Club
- Wildwoods Convention Center
- Mariner's Arcade
- Funland
- Dewey Beach Access





