
Waterfront vacation rentals in Ocean Pines
Find and book unique waterfront rentals on Airbnb
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 New Beachfront! King Bed, Direct Sea 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!!

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!

Ocean Pines Retreat
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

IslandCoveParadise:LuxNewlyBuilt-Brdwk pool/2CarGg
We welcome you, your family and friends to stay at our luxury, Newly Built, beautifully furnished, & decorated 3 BR 3.5 BA w/2 parking garage spaces plus free street parking, and an outdoor pool on 25th street. Relax and enjoy the AMAZING VIEW on the water front from our triple balconies, just 2 blocks (3-4 minutes walk) from the boardwalk & the beach. Steps from Jolly Rogers Amusement Park and many miniature golf courses. Within walking distance are restaurants/, shopping, & nightlife.

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 :)

The Hideaway By The Bay OCMD
Relax and enjoy your stay in this bright and welcoming waterfront, 1 bed, 1 bath condo. Bring your kayaks or paddle boards! This condo is located right off of 28th street, on the bay. It is a 14 minute walk to the beach and the Ocean City boardwalk, and within walking distance to many Ocean City attractions. All guests are provided with an electronic WELCOME BOOK prior to arrival which includes everything we think they will need to know about the condo and the surrounding area.

Beachfront with a View and Amenities Galore
Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with a breathtaking view of the beach and ocean.

Beach Paradise X -New Lux Garage Townhouse w/ Pool
Welcome to Island Time Townhouses! Newly built, spacious and beautifully furnished 3 bedrooms, 3.5 baths, 3 levels, luxury townhouse with garage. The community is located in prime downtown location, 1 block across from the bay, 5 minutes walk from the beach and Ocean City's famous BOARDWALK. Our new luxury townhouse is not only equipped with all modern amenities and stylish furnishings, but also offers plenty of indoor space along with a community outdoor pool.

Oceanfront 2 Bed/1.5 Bath, Balcony, Pools, Lounge
Wake up to breathtaking ocean views at Driftwood, a beautifully remodeled 2BR/1.5BA oceanfront condo in the amenity-rich Golden Sands Resort! Sleeps 6 with 2 queen beds + queen sleeper sofa. Enjoy your private balcony, indoor & outdoor pools, private beach, fitness center, game rooms, tennis, pickleball, volleyball, huge sun deck, and seasonal tiki bar. Steps to the sand and close to Northside Park, top restaurants, and the iconic Ocean City Boardwalk!

Bayfront Townhouse: Fishing, Sunsets & Family Fun!
Escape to this stunning, updated bayfront townhouse in midtown Ocean City! Featuring 3 bedrooms with 3 ensuite bathrooms, enjoy breathtaking sunsets from your private deck. This entertainer's dream offers a spacious open layout with a gourmet kitchen and waterfall countertops. Benefit from two assigned parking spots, fish directly off the back deck pier, a local favorite fishing spots, you'll love the waterfront access and relaxing atmosphere.

Charming Waterfront Cottage w/2 King Suites + Dock
Newly renovated, sparkling, spacious house with room for seven and waterfront views is waiting for you. Perfect for a single or double family getaway, girls weekend, or quiet retreat. *Please note this is a No Smoking and No Pet Property. **We are located in a quiet, residential neighborhood with lovely neighbors in close proximity. Please consider this when booking. ***We do not supply sheets and towels. Rental License #2162
Popular amenities for Ocean Pines waterfront rentals
Waterfront apartment rentals

Beautiful Direct Oceanfront Condo on Boardwalk

Pelican Beach-Oceanfront

Amazing oceanfront view 3 blocks from boardwalk

Endless Summer With Ocean View & Large Deck

Beachy Getaway

Beautiful Bayfront Condo!

Ocean Front Pools Tiki Bar Self-Check-in Parking

SuperHost! Amazing OceanFront View with 2 Pools!
Waterfront house rentals

Private pool, waterfront, kayaks, bikes, firepits!

Beach Paradise 2101-Downtown Luxury Condo Bay View

Relaxing Breezy Seaside 3bd/2ba/2decks King Bed

Oceans End Waterfront Retreat

New waterfront home on bay, quick walk to beach

Seaside Sanctuary @ Stone Harbor

Coastal Oasis in Ocean Pines

Cottage on the water
Waterfront condo rentals

Direct Oceanfront Condo with Expansive Ocean Views

Cozy oceanfront condo with stunning ocean views

Oceanfront Condo pools/Gameroom/Theatre/Restaurant

Beautiful 2BR 2BA oceanfront condo at the Atlantis

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom

Ocean front condo with Balcony

Luxury Oceanfront Escape!

Caramar Couples Retreat
When is the best time to visit Ocean Pines?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ746 | ﺩ.ﺇ834 | ﺩ.ﺇ746 | ﺩ.ﺇ815 | ﺩ.ﺇ914 | ﺩ.ﺇ1,307 | ﺩ.ﺇ1,399 | ﺩ.ﺇ1,451 | ﺩ.ﺇ1,010 | ﺩ.ﺇ845 | ﺩ.ﺇ790 | ﺩ.ﺇ768 |
| 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 |
Quick stats about waterfront rentals in Ocean Pines

Total vacation rentals
Explore 60 vacation rentals in Ocean Pines

Nightly prices starting at
Ocean Pines vacation rentals start at ﺩ.ﺇ477 per night before taxes and fees

Verified guest reviews
Over 2,050 verified reviews to help you choose

Family-friendly vacation rentals
60 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
60 of Ocean Pines vacation rentals include wi-fi access

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

4.7 Average rating
Ocean Pines stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Mount Pocono Vacation rentals
- The Hamptons Vacation rentals
- Outer Banks Vacation rentals
- Fitness-friendly rentals Ocean Pines
- Rentals with outdoor seating Ocean Pines
- Rentals with beach access Ocean Pines
- Rentals with a washer and dryer Ocean Pines
- Beachfront rentals Ocean Pines
- Rentals with pools Ocean Pines
- Rentals with a kayak Ocean Pines
- Rentals with lake access Ocean Pines
- Rentals with a fireplace Ocean Pines
- Rentals with a patio Ocean Pines
- Condo rentals Ocean Pines
- House rentals Ocean Pines
- Beach house rentals Ocean Pines
- Family-friendly rentals Ocean Pines
- Rentals with a fire pit Ocean Pines
- Pet-friendly rentals Ocean Pines
- Beach condo rentals Ocean Pines
- Apartment rentals Ocean Pines
- Waterfront rentals Worcester County
- Waterfront rentals Maryland
- Waterfront rentals United States
- Ocean City Beach
- Broadkill Beach
- Wildwood Crest Beach New Jersey
- Cape May Beach NJ
- Assateague Island National Seashore
- Ocean City Boardwalk
- Dewey Beach Access
- Willow Creek Winery & Farm
- Assateague Beach
- Pearl Beach
- Jolly Roger Amusement Park
- Big Stone Beach
- Cape Henlopen State Park
- Peninsula Golf & Country Club
- Poodle Beach
- Northside Park
- Poverty Beach
- Higbee Beach
- Bayside Resort Golf Club
- Bear Trap Dunes
- Baywood Greens Golf Maintenance
- Towers Beach
- Jolly Roger at the Pier
- Assateague State Park