Family-friendly holiday rentals in Ocean Pines

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Ocean Pines family-friendly rentals

Family-friendly home rentals with a hot tub

Home in Selbyville
4.92 out of 5 average rating, 37 reviews

Bayside * 6BR Luxury Beach House

ConnerRating, 5 stars3 weeks ago
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!
Guest favourite
Flat in Bethany Beach
4.87 out of 5 average rating, 139 reviews

Sea Colony Beach And Tennis Resort

JudithRating, 5 starstoday
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.
Guest favourite
Villa in Ocean View
4.89 out of 5 average rating, 151 reviews

3 BR 1st floor condo, near beach, resort community

KelliRating, 5 stars1 month ago
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!”
Superhost
Apartment in Bethany Beach
4.89 out of 5 average rating, 176 reviews

Beautiful Beach-View Condo

EricaRating, 5 stars3 weeks ago
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 😊
Superhost
Flat in Ocean View
4.64 out of 5 average rating, 87 reviews

Fun, Sun and Water 2br upstairs apt

AndrewRating, 5 stars11 months ago
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.
Superhost
Townhouse in Bethany Beach
4.92 out of 5 average rating, 110 reviews

Lakefront slps 6; beach, pools, tennis, gym, view!

ValeriaRating, 5 stars11 months ago
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!
Superhost
Home in Berlin
4.8 out of 5 average rating, 5 reviews

Quiet Retreat near Assateague Main House

ZacharyRating, 5 stars46 months ago
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!
Superhost
Townhouse in Selbyville
4.75 out of 5 average rating, 99 reviews

Bayside - Best Deal in Bayside!

MorganRating, 5 starstoday
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

Guest favourite
Home in Bethany Beach
4.94 out of 5 average rating, 115 reviews

Bethany Beach 116 5th St Oceanblock

LynnRating, 5 stars1 week ago
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!
Guest favourite
Home in Ocean City
4.93 out of 5 average rating, 42 reviews

West OC Bayside Getaway w/ pool

AlexandraRating, 5 stars2 weeks ago
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! :)
Guest favourite
Townhouse in Ocean City
4.94 out of 5 average rating, 84 reviews

Coastal Waterfront TH on Quiet Street

ShellyRating, 5 stars1 month ago
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.
Superhost
Home in Bethany Beach
4.92 out of 5 average rating, 37 reviews

Just renovated on canal and 1.5 blocks to beach

MariaRating, 5 stars9 months ago
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!
Guest favourite
Home in Millsboro
4.87 out of 5 average rating, 38 reviews

Boaters And Fisherman Paradise at Massey's Landing

BrielleRating, 5 stars3 weeks ago
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!
Top guest favourite
Townhouse in Bethany Beach
4.93 out of 5 average rating, 108 reviews

The Willow Haven 3 Bedroom 2 1/2 Bath

JosephRating, 5 stars3 weeks ago
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!
Top guest favourite
Home in Ocean Pines
4.88 out of 5 average rating, 59 reviews

Sunny Days

ScottRating, 5 stars8 months ago
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!
Superhost
Home in Bethany Beach
4.95 out of 5 average rating, 56 reviews

Large waterfront home on South Bethany Canal

GiavannaRating, 5 stars10 months ago
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

Superhost
Flat in Ocean City
4.84 out of 5 average rating, 126 reviews

2nd Floor 3 BR Condo Close to the beach with Pool!

JenniferRating, 5 stars8 months ago
Wonderful place and a hidden gem for the price. Definitely will be back.
Superhost
Apartment in Ocean City
4.79 out of 5 average rating, 108 reviews

Spacious Direct Oceanfront 1BR Condo w/Balconies

ChrisRating, 5 stars3 weeks ago
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!
Superhost
Apartment in Ocean City
4.83 out of 5 average rating, 36 reviews

Oceanfront High Point 4C *Pool *FREE Linens/Towels

CoreyRating, 5 stars10 months ago
Awesome view...Right on the beach. Great location. Highly recommended. Words just can't describe my stay.
Guest favourite
Apartment in Ocean City
4.95 out of 5 average rating, 59 reviews

Spectacular Ocean Front Condo on Boardwalk!

GenevaRating, 5 stars2 weeks ago
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. 😀
Superhost
Flat in Ocean City
4.65 out of 5 average rating, 89 reviews

Oasis On The Bay Amazing Bayviews. Amazing sunset.

AmandaRating, 5 stars9 months ago
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.
Superhost
Apartment in Ocean City
4.81 out of 5 average rating, 147 reviews

Welcome to a Shore Thing!

ZennaRating, 5 stars1 week ago
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.
Superhost
Flat in Ocean City
4.9 out of 5 average rating, 141 reviews

Bayside Beach Getaway

JohnRating, 5 stars1 week ago
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!
Superhost
Apartment in Ocean City
4.87 out of 5 average rating, 83 reviews

Bayside Clean and Comfortable with a Pool

JimRating, 5 stars8 months ago
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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