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
4.73 out of 5 average rating, 40 reviews

Bayside * 6BR Luxury Beach House

BreanneRating, 5 stars1 week ago
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.
Guest favourite
Apartment in Bethany Beach
4.87 out of 5 average rating, 139 reviews

Sea Colony Beach And Tennis Resort

JudithRating, 5 stars1 day ago
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.
Superhost
Condo 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 😊
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 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 stars1 day ago
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
Condo in Ocean City
4.85 out of 5 average rating, 52 reviews

⭐️CB9-Partial ocean view-Upscale Dir beach access🏖

CherylRating, 5 stars1 month ago
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!
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 stars4 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!

Family-friendly home rentals with a pool

Guest favourite
Home in Berlin
4.96 out of 5 average rating, 74 reviews

Private pool, waterfront, kayaks, bikes, firepits!

LenoreRating, 5 stars1 month ago
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!
Superhost
Apartment in Ocean City
4.84 out of 5 average rating, 127 reviews

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

KelsieRating, 5 stars2 weeks ago
Beautiful place, beautiful view, amazing time
Superhost
Condo in Ocean City
4.79 out of 5 average rating, 108 reviews

Spacious Direct Oceanfront 1BR Condo w/Balconies

ChrisRating, 5 stars4 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
Condo 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.
Superhost
Condo in Ocean City
4.83 out of 5 average rating, 58 reviews

Bayside Boaters' Paradise | Pool | Family Fun

ChristopherRating, 5 stars1 month ago
We had a great weekend stay! Amazing views, super nice condo! Make sure to bring linens, towels, and paper products.
Superhost
Condo 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
Apartment in Ocean City
4.9 out of 5 average rating, 142 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
Condo in Ocean City
4.75 out of 5 average rating, 149 reviews

Bayside - Summer Winds Complex - 2 Bedroom, Pool

CatRating, 5 stars4 weeks ago
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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