Kid-friendly holiday rentals in Ocean Pines

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Top-rated family-friendly rentals in Ocean Pines

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Guest favourite

Apartment in Berlin

4.98 out of 5 average rating, 103 reviews

Amazing Waterfront in Berlin, MD- Sea Breeze Suite

1 of 5 waterfront units (Drift Inn, Sea Breeze, Coconut Grove, Coral Tides, Day Break) located at The Inn on Turville Creek in West Ocean City. Perfect for outdoor lovers or a quiet escape. Bring your paddleboards, kayaks, or just enjoy the beautiful views from the comfort of your own patio. The Inn is located approximately 5 miles from downtown Ocean City and the town of Berlin, MD (voted America's Coolest Small Town) and ~10 miles from Assateague. Stunning sunsets right from your front patio!

16–23 Sep

₹15,781 per night

Guest favourite

Guest suite in Ocean Pines

4.95 out of 5 average rating, 354 reviews

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!

1–8 Dec

₹13,355 per night

Guest favourite

Apartment in Ocean Pines

4.96 out of 5 average rating, 109 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

25 Apr – 2 May

₹11,553 per night

Guest favourite

Home in Ocean Pines

4.89 out of 5 average rating, 141 reviews

Relaxing Home Near the Beach in Ocean Pines, MD

This is a 3 bedroom/2 full bathroom, single-story, home that is ready for you and your dogs if you have them. Guests have use of the entire house, including an outdoor grill. There is a dog door that leads to a fenced backyard. Guests have access to our beach accessories and a free beach parking pass. The house can accommodate 6 people comfortably, and up to 8 with the use of a futon. The house has a stocked kitchen. The community has many amenities that are described in the house manual.

8–15 May

₹21,632 per night

Guest favourite

Home in Ocean Pines

4.96 out of 5 average rating, 113 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

₹12,705 per night

Guest favourite

Apartment in Ocean City

4.99 out of 5 average rating, 101 reviews

Beautiful Renovated Ocean Front Condo 1b/1.5ba

Beautiful renovated ocean front condo. Get ready to relax in comfort and style! This large 836 sqft one 1b/1.5ba offers breath taking views of the ocean. You will be just steps away from the sand in one of the closest buildings to the beach. Enjoy your coffee or a different sunrise each day from your private balcony off the living room. Updated patio furniture with a cozy bench and high table with 2 chairs that bring a spectacular, completely unobstructed view of the beach and ocean.

18–25 Nov

₹13,215 per night

Guest favourite

Apartment in Ocean City

4.91 out of 5 average rating, 239 reviews

Ocean-block 36th St. - Steps to the Beach!

Comfortable and affordable, our 1 bed/1 bath - 1st floor condo is in a prime OC Mid-Town location. Literally just steps from the building to the sand! Walking distance to me of OC's best restaurants, night life, amusements, convention center and more. **Summer Months check-ins on Monday & Friday ONLY from Memorial Day to Labor Day! Book Weeks or Mini-weeks. (Weeks: Fri to Fri, OR Mon to Mon) (Mini-Weeks: Mon to Fri, OR Fri to Mon)** *Other months check-in any night*

19–26 Dec

₹8,168 per night

Guest favourite

Guest suite in Berlin

4.99 out of 5 average rating, 150 reviews

Berlin/Ocean City Suite- Relax/Refresh near beach!

A remodeled, above garage guest suite separate from the main house in America's Coolest Small Town, Berlin Md! You will benefit from a separate entrance to your above garage suite which will allow you to enjoy your own quiet space to relax and embrace the small, quaint town of Berlin, all while a mere 15 minutes to the beaches of OCEAN CITY and Assateague! Multiple dining experiences and tons of shopping await you in either historic Berlin or world famous Ocean City!

5–12 Apr

₹9,502 per night

Guest favourite

Flat in Frankford

4.98 out of 5 average rating, 123 reviews

Cozy Cottage Getaway

Enjoy this newly remolded 1 bedroom apartment tucked away on 2+ acres 3 miles from Bethany beach. Close to Rehobeth beach for outlet tax free shopping or Ocean City MD just 13 miles. You’ll be minutes away from lots of restaurants, stores, mini golf, arcade, night life etc. Property includes a 1/4 mile walking/running trail, fire pit and basket ball court. This is the perfect place to escape away from the busy Beach life but close enough to enjoy everything fully.

7–14 May

₹7,805 per night

Guest favourite

Barn in Selbyville

5.0 out of 5 average rating, 149 reviews

Ranch Stay- Farm Animals, Jacuzzi, Arcade, Beaches

Welcome to the Swedish Cowboy, your perfect place to escape the daily grind and experience something truly unique! This BARNDOMINIUM home is just minutes from a waterpark, beaches, boardwalks, and features an entire barnyard of fuzzy and feathered animals ready to meet you! You will enjoy amenities like a relaxing jacuzzi, a 5-foot tall arcade, toys for the kids and tons of nearby restaurants. Staying at Cowtown Cabins is like having two vacations rolled into one!

6–13 Nov

₹10,140 per night

Guest favourite

Home in Ocean Pines

4.99 out of 5 average rating, 101 reviews

Charming Waterfront Cottage w/2 King Suites + Dock

Newly renovated, sparkling, spacious house with room for 7 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 Property. **We are located in a quiet residential neighborhood with lovely neighbors in close proximity. Please consider this when booking. ❤️

28 May – 4 Jun

₹30,387 per night

Guest favourite

Cottage in Berlin

4.99 out of 5 average rating, 120 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 Jan

₹13,683 per night