
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.
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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
This house was everything we were looking for. Everything looks just like pictures! This is one of the firsts homes where the WiFi worked and the cable was also working. Very clean home and we were excited to take use of the grill! 10/10 would love to come back one day!

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.

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!”

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 😊

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.

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!

Large waterfront home on South Bethany Canal
We had a great stay at Wenxin’s house! The location was perfect with just a short walk to the beach and we loved the canal and backyard area. We have young kids and found it to be a perfect spot. There was even a crib, pack and play, and toddler bed which was awesome. Wenxin was very responsive and helpful when we arrived a little early. Would definitely stay here again!
Family-friendly home rentals with a pool

2nd Floor 3 BR Condo Close to the beach with Pool!
Wonderful place and a hidden gem for the price. Definitely will be back.

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.

Spectacular Ocean Front Condo on Boardwalk!
Excellent vacation. Was a great location right on the boardwalk. I enjoyed people watching and loved watching the little tikes. The condo was beautifully designed and a great layout. Every bedroom was like its own little suite with private bathrooms. The master suite was just like the pictures and very large and comfortable. I loved having the extra hangers to get my clothes out of the suitcase ❤️. We also enjoyed the extra pillows, and blankets available. Steve was very helpful in arranging my linen rental for the time we were there. We enjoyed home cooked meals as well as eating out and everything we needed was right there. Such a great host!! Will definitely look forward to staying again. Was more than I expected and definetly worth the rental fee. Thank you so much. 😀

Oasis On The Bay Amazing Bayviews. Amazing sunset.
Was a great place to stay for our weekend getaway! Very beautiful view, close to the beach, shops and restaurants. The little pool right on the water was great as well.

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 Clean and Comfortable with a Pool
We had a fantastic time at Tina’s place! The location was perfect—just a short walk to the beach, boardwalk, and great restaurants. The space was cozy and clean and had everything we needed for our group of 7. Tina was a fantastic host, super responsive, and helpful throughout our stay. The check-in process was smooth, and off-street parking was a huge plus for our F150. The little library was a cute touch, and the overall vibe was perfect for relaxing after a fun day. Tina made sure we were well taken care of. We truly enjoyed our time here and highly recommend this spot to anyone visiting OCMD. Thanks again for an unforgettable stay, Tina!
Quick stats about holiday rentals that are family-friendly in Ocean Pines
Total rentals
260 properties
Nightly prices starting at
₹3,462 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
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