Family-friendly vacation rentals in Ocean Pines

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Ocean Pines

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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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!

Nov. 13 – 20

$272 CAD per night

Guest favourite

Condo in Ocean City

4.82 out of 5 average rating, 124 reviews

1 BR Ocean Block (Unit 17) 40th St Midtown OC

Renovated ocean block condo with vintage charm & modern amenities. Second floor walk-up. Wonderful covered balcony for enjoying the sea breeze. Only 75 yards away from the beach. The Mid-Town OC location offers the best of everything...close to the boardwalk but far from the noise, great restaurants & bars within walking distance. Enjoy live music & a drink on the beach at Coconuts, only 9 blocks to Jolly Roger or Secrets. Walk to the OC Convention Center just across Coastal Hwy on the bayside.

Dec. 13 – 20

$153 CAD per night

Guest favourite

Guest suite in Ocean Pines

4.95 out of 5 average rating, 353 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!

Dec. 10 – 17

$260 CAD per night

Guest favourite

Condo in Ocean City

4.91 out of 5 average rating, 255 reviews

Ocean Front 802 Midtown Oasis Pool & Parking

Wake up to the ocean sunrise in this modern 2 bedroom, completely renovated, condo. Prime location on 29th street, 2 blocks north of the famous OC Boardwalk, 2 blocks east of OC's premier amusement and water park along with two famous crab house and other restaurants within walking distance. One hassle free off street parking spot, free WIFI, full size washer & dryer, and a beautiful outdoor pool steps from the beach. Enjoy the bay sun set view out the front door and fall asleep to the waves.

Feb. 5 – 12

$342 CAD 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.

May 14 – 21

$418 CAD per night

Guest favourite

Condo in Ocean City

4.99 out of 5 average rating, 106 reviews

Cozy & Clean Condo on 36th st. Steps to Beach!

NOT A PARTY PLACE! If that is what you are looking for please keep scrolling!! Well taken care of 2nd floor condo conveniently located on 36th street and is just steps away from the beach. Great place to stay with family or friends with the ability to quickly come and go from beach as you wish with no need to get in a car. Close to convention center, Seacrets, and Jolly Rogers. Sleeps 4 adults comfortably. Convenient keypad entry so no need to worry about losing a key! MUST BE 25+ TO RENT!!

Jan. 27 – Feb. 3

$275 CAD per night

Superhost

Home in Rehoboth Beach

4.79 out of 5 average rating, 621 reviews

Contemporary 1 Bedroom 2 level home

The unit has keyless entry system, A/C, brand new full size W/D, large patio w/grill, remote controlled open&close sky lights w/built in shades, new carpet, YoutubeTV/Netflix/Hulu/Amazon Prime Video & walk to the beach and attractions w/out crossing **pet friendly** **LOCATION** Intersection of Washington st & Jefferson St. supplied for guest: sheets blankets bath towels Shampoo/conditioner soap toilet paper paper towels trash bags Back pack type beach chairs (3) Beach umbrella Bikes (2)

Feb. 24 – Mar. 3

$179 CAD 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

May 13 – 20

$158 CAD per night

Guest favourite

Home in Ocean View

4.92 out of 5 average rating, 530 reviews

Tiny House at Good Earth, near Bethany Beach

A custom-built "Tiny House" located right between our new dinner theater and our garden dining area. True to the show "Tiny House Nation"; cool interior with custom woodwork, stairs to a lofted bed. Fully functioning kitchen. Spacious bathroom & shower. We provide TVs and internet in the units but the quality of service is not guaranteed. We are in a rural area and sometimes it's slow or not working at all. If TV and internet are super important for your stay we may not be the right fit.

Dec. 21 – 28

$188 CAD per night

Guest favourite

Condo 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*

Dec. 26 – Jan. 2

$171 CAD per night

Superhost

Condo in Ocean City

4.88 out of 5 average rating, 106 reviews

Unit 11 on 41 St Ocean Side 50 steps to beach

Dominica Beach is a 2-story condo, close to the ocean on 41st Street Only 50 paces to the sand dunes and you'll have your toes in the sand! There are no streets to cross to get the beach. Complementary linen service based on the number of guests. Within walking distance of the Convention Center, restaurants, amusement parks, mini-golf, & more. You’ll love our place because of the ambiance. It is good for couples, solo adventurers, and families (with kids).

Nov. 16 – 23

$139 CAD per night

Guest favourite

Condo in Ocean City

4.99 out of 5 average rating, 175 reviews

Direct Oceanfront close to Northside Park!

Location, location, location! 2 bed, 2 bath direct oceanfront condo, with incredible ocean sunrise views from your private enclosed patio. Master bedroom features unbelievable views of the ocean, glass slider out to the patio & in suite full bath! Walking distance to Northside Park, restaurants & shopping. 2 assigned parking spaces. Elevator or steps - you pick. Washer/dryer in unit.

Feb. 1 – 8

$212 CAD per night