
Family-friendly holiday 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.
Holiday rentals for every style
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Popular amenities for Ocean Pines family-friendly rentals
Family-friendly home rentals with a hot tub

Bayside * 6BR Luxury Beach House
From the moment you walk through the door, a warm, welcoming atmosphere greets you. The house has soft carpets that feel perfect on your feet after a day on the beach, and even more perfect showers that provide a relaxing bliss to start or end the day. The kitchen is very cozy and perfect for simple lunch with friends. The bedrooms are spacious with large windows that opt for privacy depending on your preference. Overall, the stay, for me and family, was extremely enjoyable and we would stay again without a doubt.

Sea Colony Beach And Tennis Resort
Beautiful, clean home that was perfect for vacation for family of 7. Great location with lots to do. We took advantage of the fitness facility, pool, beach, pickle ball, playground, community grills, tram and Sea Colony shops. Caroline was extremely easy to communicate with as she was highly responsive and proactive in providing helpful information. Would definitely recommend.

Beautiful Beach-View Condo
We loved Raj’s place! We have two young children and his place was fully equipped to entertain them with books, toys, etc. Best Airbnb we have stayed in so far 😊

3 BR 1st floor condo, near beach, resort community
We appreciated your quick responses and helpful recommendations. Staying with Beth was a pleasure. The location was perfect, the home was cozy and Beth was always available to answer our questions. Highly recommended!”

Fun, Sun and Water 2br upstairs apt
Don was a great host. From the moment I arrived my dog Dizzie and I felt like valued guests. Don provided some great recommendations for things to do locally, and was always available if anything came up. The space was very clean and I could tell Don put a lot of effort into creating and maintaining it.

Lakefront slps 6; beach, pools, tennis, gym, view!
Sherri’s place is awesome and the community and surroundings are beautiful. The kitchen is furnished with everything you need for cooking. The deck is such a plus, with the view of the pond and the ducks, as well as the private little beach. The community is very friendly and walkable, and the different options for pools were very fun for us to explore. Taking walks in the morning was amazing. It is very close to Bethany “downtown” and 6 min drive to the beach. You can also walk or take the tram. I had a great time with my kids and would definitely recommend and come back!

Quiet Retreat near Assateague Main House
What a truly incredible place and host! I can’t say enough about Kate’s responsiveness and the incredible space. We loved it and hope to be back again!

Bayside - Best Deal in Bayside!
We loved the location, right across from one of the pools! Lots of steps but it’s a great property and plenty of room for everyone! Would definitely stay again!
Family- and pet-friendly home rentals

Bethany Beach 116 5th St Oceanblock
We loved our stay! The house was beautiful with lots of space and exceptionally well stocked. The pictures really don’t do it justice. We spent a lot of time on the very comfortable screened in porch. A few nice surprises: the water pressure was fantastic, the washer and dryer are huge, and there was ample fridge space upstairs and a second one on the first floor. Paul was also very responsive during our stay and very nice! We’d love to come back again!

West OC Bayside Getaway w/ pool
I highly recommend this house! Doug is a very helpful and responsive host. The house is just as pictured in the photos and very clean. The location is also ideal - private but close to everything! The deck and patio in the backyard are beautiful and right on the water. The pool is also very clean and relaxing. I don’t have one bad thing to say about this house, and I can’t wait to come back next summer! :)

Coastal Waterfront TH on Quiet Street
the home was beautiful, quiet, orderly. we stopped at the wrong 13450 first and was confused we couldn't find 17.....we were in DE still. it was funny as we searched and finally realized we needed to go a few more feet to MD. I would definitely stay again.

⭐️CB9-Partial ocean view-Upscale Dir beach access🏖
Perfectly as described. Partial ocean view with a one minute walk to the beach. Great location! Nice little porch area to sit and have morning coffee. Very spacious inside and very clean. Hollin was very responsive when I had a question. We loved our stay and would definitely go back and stay again!

Just renovated on canal and 1.5 blocks to beach
We had a very nice stay with a large group of teens. They could walk to the beach on their own and the house was big enough for everyone. Joey neighborhood. Thank you!

Boaters And Fisherman Paradise at Massey's Landing
My husband and I loved our stay! It was super easy to access Masseys Boat ramp from the Airbnb. We would 100% stay here again!

The Willow Haven 3 Bedroom 2 1/2 Bath
We really enjoyed our stay at David and Erin’s Willow Haven! The condo was super clean, beautifully updated and with plenty of space for our family of adult children. The location was great with restaurants, gourmet market and coffee shop a few steps away. We walked or enjoyed their provided bikes for a ride down the beach every day. David was super responsive, left clear instructions and accommodated any request we had. This was our first, and certainly not last trip to Bethany Beach and look forward to staying at Willow Haven again!

Sunny Days
Sunny Days is a fun place for a family gathering - in our case to attend a festival. Bill+ are great hosts: you know upfront everything about the property, and they deliver!! Wonderful hosts!
Family-friendly home rentals with a pool

Private pool, waterfront, kayaks, bikes, firepits!
We can't wait to return to Golden Quarter Farm! Charming and expansive, the property has everything we were looking for in a place to spend a relaxing weekend with extended family. The historic house is bright and roomy with a well-appointed kitchen; the bedrooms are unique, comfortable, and private; and the living space homey and inviting -- perfect for spending time together. The beautiful views of the riverfront drew everyone outside for walks down the pier, through the fields, and down the sun-dappled forest trails. It was a bit too chilly during our April stay, but the possibilities for enjoying the river (canoe, kayay, SUP) and lovely pool were nonetheless enticing. Finally, I must mention that Evie and Mary were extraordinarily welcoming and accomodating, from communicating proactively to preparing the home for our stay and checking in to make sure everything was perfect. Highly recommend!

2nd Floor 3 BR Condo Close to the beach with Pool!
Beautiful place, beautiful view, amazing time

Spacious Direct Oceanfront 1BR Condo w/Balconies
Location was excellent right on the beach with a beautiful view of the ocean. The property was easy to find and the security guard at the front desk was super helpful getting us squared away with anything we needed. The condo had great amenities including a nice big fridge and stove, not to mention it has cable television for when you are relaxing (most Airbnb's do not offer this). 5/5 stars for everything except the bed (I am used to a firm bed and this one was beyond soft). We would absolutely stay here again though and I highly suggest this place for a nice getaway. Thanks, Natallia, for being a great host!

Oceanfront High Point 4C *Pool *FREE Linens/Towels
Awesome view...Right on the beach. Great location. Highly recommended. Words just can't describe my stay.

Bayside Boaters' Paradise | Pool | Family Fun
We had a great weekend stay! Amazing views, super nice condo! Make sure to bring linens, towels, and paper products.

Welcome to a Shore Thing!
We had a pleasant and comfortable stay. We had everything we needed and it was very nice that some toilet paper, paper towels, and soaps were included when we got there.

Bayside Beach Getaway
I come to Ocean City every June with a couple of my employees for an annual conference and we always get an AirBnb, Bayside Beach Getaway was perfect! The location was excellent for us and close to everything, much of it within walking distance; restaurants, convenience stores etc as Coastal Hwy was just 50 ft away. The host communicated with me quickly and clearly and the check-in was flawless. When we arrived, we found a very nice, very clean condo with plenty of room. Our schedule was such that we ate breakfasts and lunches at the condo before and after the conference. The kitchen was well stocked with everything we needed to cook our meals. We enjoyed sitting out on the deck in the evenings which overlooked the water. I would highly recommend this condo!

Bayside - Summer Winds Complex - 2 Bedroom, Pool
Awesome host, quick response. Nice quiet neighborhood and place was clean. We were a little bummed the pool wasn't open for Memorial weekend but it's okay we went to the beach. All the instructions were clear. Close to everything.
Quick stats about holiday rentals that are family-friendly in Ocean Pines
Total rentals
260 properties
Nightly prices starting at
$67 NZD before taxes and fees
Total number of reviews
7K reviews
Pet-friendly rentals
80 properties allow pets
Rentals with a pool
140 properties have a pool
Rentals with dedicated workspaces
130 properties have a dedicated workspace
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- Ocean City Beach
- Broadkill Beach
- Assateague Island National Seashore
- Cape May Beach NJ
- Mile Beach
- Higbee Beach
- Poverty Beach
- Ocean City Boardwalk
- Dewey Beach Access
- Cape Henlopen State Park
- Jolly Roger Amusement Park
- Willow Creek Winery & Farm
- Towers Beach
- Northside Park
- Assateague Beach
- Bayside Resort Golf Club
- Jolly Roger at the Pier
- Poodle Beach
- Delaware Seashore State Park
- Pearl Beach
- Wildwood Dog Park & Beach
- Peninsula Golf & Country Club
- Heritage Shores
- Killens Pond State Park