
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

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!

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!

Captivating A-Frame in beautiful, Ocean Pines
Overall a great stay! The house was beautiful and in an awesome location. Lots of things provided free of charge, such as toiletries, frozen food, cleaning supplies, and others. These appeared to be leftover from previous tenants, but neatly tucked away. I like that they aren't wasteful with perfectly good supplies. One light in the kitchen appeared to have been turned on while we went out once. the rustic, retro style was a huge hit for us and we're very appreciative of the hospitality for the duration of our stay here!

*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. 🦀

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
Wonderful home in a very peaceful area. Beth was very responsive to questions we had and gave detailed instructions on checking in and out. The home is a perfect size, and we really enjoyed the three season room as a quiet area in the mornings.

Private, pet-friendly, w/game room & new kitchen
Maria, the host was wonderful. Each time I sent a message she responded quickly. Had a beautiful week especially for the beach. Would definitely rent again and other properties owned by Maria. Nothing against the host, Airbnb fee should be less and the cleaning fee is to high

Robin Hood Retreat
Bill is a wonderful , polite. ,accurate and a cool host. The house was neat and clean. Bill made sure you have fresh linens for each bedroom. He was easy to get in contact with.Bill makes you feel at home.The house is beautiful and in a peaceful area!( The pictures does not do this house any justice) Bills house is safe and secure. Bill has many properties and I will be booking again. Thanks bill for everything. You are great!!
Condo rentals with a pool

Pondview Villa: Beach Club Gem
5 Star accommodations, like new! The kitchen had all of the tools, gadgets, pots, pans to help feel at home. We stayed off season (last week of April). We were the only people in the building. Note: for off season guests, the pool isn't open yet. The beaches, trails, and restaurants all nearby made it easy to explore and then return to relax in comfort. We sat on the deck, hung out by the pond with comfy chairs and enjoyed the sunsets. Our 1 1/2 year old Weim dog settled in nicely. We were grateful for water and food bowls provided. If you're staying with kiddos or friends, there is a hidden gem- lots of games tucked away in the coffee table. What a nice touch! All of the instructions for the home were simple, easy to follow. Note: This condo is on the 2nd floor. Easy for us, but may be difficult for some.

Wight Bay Unit 245
we had a great stay for Country Calling! highly recommend!

Luxury 2BD Condo, Walk to Beach, Pool&Tennis Court
From the moment we walked in, we were blown away. This condo is gorgeous—beautifully decorated, modern, and clearly designed with adults in mind (no mismatched beachy knick-knacks here!). It strikes that perfect balance of cozy and upscale, with top-of-the-line appliances and thoughtful touches throughout. You can tell a lot of love and care went into creating this space. And the best part? It’s just a block from the beach! We felt instantly at home and didn’t want to leave. If you’re looking for a peaceful, stylish getaway in Ocean City—this is it. Can’t wait to come back!

🏖 *Ocean *Ocean *Ocean* 🏖 Beautiful Condo!!
We had a fantastic stay at Adam’s place. Location was amazing and the description of the unit was exactly on point. Place was clean and comfortable and even had some toys and games for the kiddos! Great communication with the host and we’ll definitely be back!!

Oceanfront Condo: Beach, Pool & Balcony Views!
Spacious and great view! Appreciate the kid-friendly touches like dinnerware, cups.

🌊Oceanfront studio w/ amazing views & amenities🏖
Lisa was an amazing host. My mother and I had a wonderful OCMD experience! Lisa was so kind and kept in touch throughout our visit. Thank you! We will be visiting again! 😊

Gone Coastal *Pool* Bayside with view* Top Floor
The place was amazing, easily fit my family (5) of us. The condo looks exactly like the pictures, very clean, had games in the closet. I would definitely come back here to stay in the furture.

BaysideGetaway | 2 Blk to Beach & Boardwalk | Pool
Nice place, in a good location for the beach and boards.
Quick stats about vacation rentals with a pool in Ocean Pines
Total rentals
140 properties
Nightly prices starting at
ﺩ.ﺇ147 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
- Ocean City Boardwalk
- Poverty Beach
- Dewey Beach Access
- Cape Henlopen State Park
- Jolly Roger Amusement Park
- Willow Creek Winery & Farm
- Northside Park
- Towers Beach
- Bayside Resort Golf Club
- Jolly Roger at the Pier
- Assateague Beach
- Poodle Beach
- Delaware Seashore State Park
- Pearl Beach
- Peninsula Golf & Country Club
- Whiskey Beach
- Wildwood Dog Park & Beach
- Bear Trap Dunes