Holiday rentals with a pool in Ocean Pines

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Top-rated rentals with a pool in Ocean Pines

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Guest favourite

Home in Ocean City

4.94 out of 5 average rating, 218 reviews

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!

13–20 Nov

£161 per night

Guest favourite

Apartment in Ocean City

4.89 out of 5 average rating, 152 reviews

Prime Condo North OC 2 Blocks to Beach w/ Pool

Pristine condo in North Ocean City with every amenity you can imagine welcomes guests over 21. Rare end unit offers more space than similar units. Two blocks from beach/park makes this the best location in town - fabulous sunset views and pool (Memorial thru Labor Day). 2 bedrooms and 2 stories offers spacious options for 6 guests to spread out. Full kitchen with everything, washer/dryer, central heat/air, Smart TV’s to access your streaming channels High Speed Internet and starter items

17–24 Feb

£72 per night

Guest favourite

Apartment in Ocean Pines

4.96 out of 5 average rating, 108 reviews

Waterview 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

1–8 Nov

£146 per night

Guest favourite

Home in Berlin

4.78 out of 5 average rating, 174 reviews

OC, Md great amenities in community, near beaches

MERMAID DREAMS where you can just have FUN or just RELAX. We are 5 miles out from OC and Assateague beaches. Our community, Assateague Pointe, is a beautiful gated community, with 2 great pools, baby pool, big splash pool, a rec center, a fishing/crabbing pier, pond with paddle boats, 2 playgrounds+ more. For kiddos of all ages, we are located right next door to Frontier Town, which has awesome water slides , western shows, mini golf, a rope course, ice cream shop.. short term stays ONLY

13–20 May

£94 per night

Guest favourite

Home in Ocean Pines

4.96 out of 5 average rating, 112 reviews

Little house in Berlin, Md.

Our home is located in Ocean Pines, Maryland. Spend the day at the beach, golf, come back and relax on our spacious screened porch. The community has 5 pools, walking trails, Parks, and more. The house is a short drive to Ocean City, Md. (8 Miles) via Rt. 90 or Rt. 50. Assateague Island National Seashore is also just a short drive 12 miles. You can see wild horses, beautiful sunsets, ride bikes, or go to the beach. There are many golf courses within 15 miles of the house all very nice.

8–15 Dec

£148 per night

Superhost

Apartment in Ocean City

4.85 out of 5 average rating, 100 reviews

2 Bdrm Oceanfront-Pool, Xbox, Pickleball, Gym, HBO

Stunning newly renovated 2 bedroom oceanfront condo in the premiere Golden Sands! Blue Wave is known for its unique 3-tiered wave wall and incredible ocean views from the living room and primary bedroom. SmartTV w/Xbox! Wake up to the sun rising over the ocean right out your bedroom window, and after a cup of coffee on the balcony (included!) head to the building's sun deck,fitness center, lounge, arcades, tennis court, pickleball court,beach volleyball,or indoor/outdoor pools and tiki bar.

25 Oct – 1 Nov

£151 per night

Guest favourite

Townhouse in Ocean City

4.95 out of 5 average rating, 101 reviews

IslandCoveParadise: Luxury-NewlyBuilt/Brdwalk/Pool

We welcome you, your family and friends to stay at our luxury, Newly Built, beautifully furnished, & decorated 3 BA 3.5 BR 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.

25 Jan – 1 Feb

£126 per night

Guest favourite

Apartment in Ocean City

4.9 out of 5 average rating, 114 reviews

A Serene Beachfront Getaway - 2 BR St. Tropez OC!

St. Tropez is a seaside resort with all rooms featuring private balconies with varying ocean vistas, from partial side views to full oceanfront panoramas. This 2 bedroom condo features 2 bathrooms, a full kitchen, living room, a dining area, and an in-unit washer/dryer. Onsite amenities combine the conveniences of home with the excitement of a beach vacation, with beachfront access, free Wi-Fi and a seasonal pool to enjoy. This oceanfront resort is located in the heart of Ocean City, MD.

1–8 Dec

£130 per night

Guest favourite

Apartment in Ocean City

4.88 out of 5 average rating, 143 reviews

Ocean Front Sea Terrace 209 Heated Pool

Three bedroom if you include the private den with a Queen Serta pullout Sofa. Low Floor and Rare TWO Parking Passes (2nd spot may not be avaiable May -Sept)! Enjoy your morning coffee on your private ocean front balcony or from the comfort of living room couch. Our ocean front retreat is an end unit (next to stairway- skip elevator lines) with ocean views including large heated pool and tennis court. Conveniently located 88th Street within walking distance of many OC's favorites.

8–15 Jan

£165 per night

Guest favourite

Apartment in Ocean City

4.97 out of 5 average rating, 225 reviews

Direct Oceanfront 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 full 100% view of the beach and ocean.

27 Nov – 4 Dec

£181 per night

Superhost

Home in Ocean Pines

4.88 out of 5 average rating, 115 reviews

Tortuga Cottage: Your All- Season Getaway

This is an escape to reacquaint with family, nature, and your best self. Come home from the beach just a few miles away to enjoy the gas fire place, outdoor fire pit, and hot tub on chilly nights, fenced in back yard. Take advantage of the parks indoor outdoor pools golf yacht club, just moments from the cottage. Dogs are part of our family, and we are happy to consider canine guests on a case by case basis. Please see policies for breeds.

9–16 Oct

£221 per night

Guest favourite

Apartment in Ocean City

4.99 out of 5 average rating, 180 reviews

Cozy oceanfront condo with stunning ocean views

Fully updated 1 bed/1 bath oceanfront condo in a quiet, mid-rise building with a beachfront pool in uptown OC. The perfect unit for a quick romantic getaway, long weekend, or family vacation. ***Summer Season: Memorial Day - Labor Day *** -7 Nights, Fri-Fri or Mon-Mon -3 Nights, Fri-Mon -4 Nights, Mon-Fri ***Off Season: Labor Day - Memorial Day*** -Any 2 Nights

20–27 Sept

£168 per night