
Vacation rentals with a pool in Ocean Pines
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Ocean Pines
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Ocean Pines rentals with a pool
House rentals with a pool

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB
Beautiful spot! Great location, close to all the happenings of Ocean City, but peaceful and quiet at the house…perfect set up. Great neighborhood. The house is beautiful, all the beds very comfortable. The back deck is gorgeous, thoroughly enjoyed that space and taking the kayaks out on the canal! It’s worth bringing your own linens and towels, we packed everything into a large tote and it worked out perfectly. Very responsive and friendly host! We had a great time here and plan to return. Highly recommend!

*Catch Me By The Sea*
We had a really lovely stay. We appreciated the thoughtful communication and local recommendations. We especially enjoyed the backyard and beach ammenities. Perfect little spot if you're looking to stay outside of the hassle and bussle of OC and in the quaint village of OP. Would highly recommend this spot for anyone looking for a good value in a sweet little town. 🦀

Amazing 2 Bedroom home close to the beach!
We needed a small place to stay for a few days and this was the perfect place for the two of us; it was cozy, spotless, well equipped for all that we needed and the decor was beachy which was perfect for the area. Jacob was quick and attentive to any question we had - it was so quiet and peaceful outside. It was a perfect getaway for us - we would highly recommend to anyone needing a nice, quiet place in the future. Thank you!!!

OC MD trip bayside, great amenities
Absolutely wonderful hosts!! Very responsive and helpful. There might have been an issue with the lockbox so they called ahead to make sure we could get in! I will definitely be booking with Shawn and Terri again!

Beautiful Spacious 4 Bedroom Home in Ocean Pines
My family and I find this place to feel like home. Very clean the host was very responsive to any questions I had prior to the date of the event. The price was just right for all that we received. The place was private with much to do and the surrounding area. I definitely will be coming here when I visit Home again .This place was big enough for my family of eight to enjoy themselves to the fullest. Thank you again.

Close to OC, Family Friendly, Pool Access
This was my very first time using an airbnb and Beth set the bar high! I honestly don't know if i could ever stay in a plan old hotel room ever again. She was helpful and responsive from the day we made the reservation all the way through and including our checkout. Beth created a welcome package that made acclimating to her home a breeze. Her house was clean, organized and stocked with all the essentials. What was advertised in the photos and description is exactly what was provided. She even had a wide variety of games to play! As far as location, it was just the right distance away from the hustle and bustle of the beach. We were able to go enjoy our day and then return to the quiet and peacefulness of her home to get a good night's sleep. Her home was also convenient to shopping within 15 minutes of driving. Checkout was easy and without a housekeeping cart sitting in the hallway, I didn’t feel rushed. So if you're planning to visit OC, Beth's house is right for you.

Charming Home in a Beach Town Community!
Ocean Pines is the perfect location- 20 minutes from the beach and lots of activities in Ocean City but a nice quiet and peaceful place to come back to to relax and enjoy the night with family. This house was a great size with really nice showers and plenty of space. We got the resident rate to visit the Ocean Pines pools which was very nice.

Entire Home w King Bed in Peaceful OceanPines 🌊🌲
This was our second stay at this beautiful home that was perfect for my family to celebrate Thanksgiving! Fantastic location, 15 min to the beach, restaurants and stores a few minutes away, everything we needed if we forgot anything or didn’t feel like cooking. The beds were super comfortable and the open floor plan was perfect our family to hang out!
Condo rentals with a pool

Sea Colony Premier Family Resort
Great place to stay at Sea Colony. The place was very nice and looked just like the pictures, and the amenities at the resort were excellent. My husband loved the open pickleball play and we both liked the pools and tram. Great location between many beach towns and boardwalks.

Oceanfront Family Oasis: Pool, Beach & Parking!
Great place to stay in Ocean City! clean and wonderful place situated right off the beach secluded and quiet. had lots of beach materials for use. would stay again.

Luxury Bay & Oceanview Condo in the Heart of Dewey
It was truly the perfect location to stay for my son’s wedding which was at the Hyatt Place right next door! An amazing experience all around from the beautiful beach decor, lovely views of the bay & ocean & convenience of walking everywhere in Dewey! The condo was clean, nicely furnished & had a well-equipped kitchen to make us feel right at home. The host was very welcoming & quick to respond to any questions we had. The wedding venue was beautiful and our stay here made the weekend even more special! It will always be one of my favorite memories.

New Updated Direct Oceanfront Condo - Pool & Wifi!
Listing is better than you think it is! Great location (I was nervous about it because we usually stay closer to 120th St) it was very private and peaceful. Big bonus that it is right over the bridge (no extra traffic lights!) The kitchen is fully stocked - we wound up bringing a lot that we didn’t need. The pullout couch is also one of the most comfortable I’ve ever been on. Beautifully decorated and updated. Might book again this season!

Top Rated! Beautful Sunsets! Midtown Bayside Condo
Raphaelle is a great host and our stay was amazing. With great views and an accommodating place, would certainly return!

🌊Oceanfront studio w/ amazing views & amenities🏖
I had a peaceful, relaxing time and enjoyed the ocean view and the sound of the waves. Lisa was extremely communicative and made sure I had everything I needed for a great stay.

BaysideGetaway | 2 Blk to Beach & Boardwalk | Pool
Was an adorable place! It was perfect for the weekend away! It was within walking dostance of the beach and boardwalk. Matthew was amazing with his instructions on how to locate the home. He was very quick to respond and extremely kind. Highly recommend this place!

Direct Ocean Front/Gorgeous Views/Indoor Pool
My husband and I decided to go on a getaway last minute. We found Seth’s place and were able to book the unit for the days we had available. It was great and met all of our expectations. We have been to OC and Fenwick many times and knew this is where we wanted to stay. It did not disappoint and we hope to rent again in the near future.
Quick stats about vacation rentals with a pool in Ocean Pines
Total rentals
140 properties
Nightly prices starting at
G$8,372 GYD before taxes and fees
Total number of reviews
3.4K reviews
Family-friendly rentals
140 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
90 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
- Jolly Roger at the Pier
- Bayside Resort Golf Club
- Poodle Beach
- Delaware Seashore State Park
- Pearl Beach
- Wildwood Dog Park & Beach
- Peninsula Golf & Country Club
- Plantation Lakes Golf and Country Club
- Heritage Shores