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, 219 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!

15–22 Jan

$241 NZD per night

Guest favourite

Condo 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

16–23 Nov

$149 NZD per night

Guest favourite

Condo 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

$302 NZD 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

$308 NZD per night

Superhost

Condo 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

$313 NZD 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.

22 Feb – 1 Mar

$261 NZD per night

Guest favourite

Townhouse in Millville

4.97 out of 5 average rating, 169 reviews

⛱ Quiet 3 Bed Twinhome just 3 miles from Beach! ⛱

Enjoy this Beautiful 3 Bedroom & 2.5 Bath Twinhome in Millville, DE. Perfect for Families! This home is within walking distance or short drive to Restaurants, Shops, Grocery Store and other Attractions & Most Importantly - only 3 miles to THE BEACH!! There is a Community Pool in the neighborhood. Many Toys, Games, Puzzles available for children. Home is No Smoking of Any Kind. Also No Pets, No Large groups/parties (12 people max.) or Senior Week rentals permitted. Book Today!

25 Oct – 1 Nov

$267 NZD per night

Guest favourite

Condo 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

$376 NZD per night

Guest favourite

Apartment in Ocean City

4.96 out of 5 average rating, 168 reviews

Everything Under The Sun-Gorgeous Ocean&Bay Views!

NEWLY and FULLY RENOVATED!!! An efficient space in a GREAT location for your next beach getaway! Upon arrival, no need to get back in your car- walk to breakfast/lunch/dinner/late night hangouts, grocery, mini-golf, OC Center of the Arts, playground, beach or Assawoman Bay. Full kitchen for your convenience if you choose to dine-in. One reserved parking spot in the condo lot. Oceanfront pool with large concrete pool-deck! Fitness Center & coin operated laundry facility.

8–15 May

$336 NZD 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

$460 NZD per night

Superhost

Condo in Ocean City

4.89 out of 5 average rating, 164 reviews

🌊Oceanfront studio w/ amazing views & amenities🏖

Efficiency/studio condo oceanfront. Queen size Murphy bed, couch, loveseat, full kitchen, bathroom, washer & dryer, ac/heat, parking, awesome amenities. This building is beautiful with amazing views. We clean & stock this condo ourselves so you'll get the owners personal touch without the crazy extra fees that rental companies charge. I love to make everyone's stay as wonderful as possible. Please read entire listing.

26 Nov – 3 Dec

$309 NZD per night

Guest favourite

Cottage in Berlin

4.99 out of 5 average rating, 119 reviews

Bayfront Cottage w/ Amazing Views

Whether you’re enjoying time by the firepit or sipping coffee on the couch, the views of Sinepuxent Bay and Assateague Island make this cottage the ideal spot for your next vacation. The cottage is located in a quiet neighborhood and is only a short drive from Assateague Island, the historic town of Berlin, and the Ocean City Boardwalk.

24–31 Mar

$323 NZD per night