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

Stoney Spring Overlook
This BnB is in contention for my FAVORITE stay of all time. Family of 6 adults and 1 child had more than enough space, and Jeanne really made our stay effortless. We felt right at home and we didn't have to make that last minute trip to the store you sometimes have to make bc the host skimped on providing toilet paper or dish soap, because she honestly thought of EVERYTHING ❤️ My granddaughter loved the pool and dips in the hot tub after swimsmade the adults happy. The location and view are to die for, and the two pups were ecstatic playing in the large fenced area. We spent a lot of time outside, plenty of furniture, fire pit, just eating dinner on the deck. (Missing NOTHING in the kitchen either!) Our last night we spent sitting and talking on the deck trying to identify the multitude of frog voices from the pond, before we parted ways to our various home states. I am most grateful for memories made and we are definitely considering a repeat! ❤️Thank you!

Bay Breeze Retreat
Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.

Gorgeous, waterfront home - Perfect for Families.
Clare and Chris could not be nicer and easier to work with. My family/friends have been getting together since 1994 and have been to many great Airbnb's and VRBO's. My group could not stop telling me how great of a week we had. The primary features that were import to us which the house scored big are as follows: It has a dock (we arrived via boat), The kitchen is big, laid out for many "Cooks", The kitchen was open to the dining room table, The dining room table is open to the sitting areas, The pool was clean and inviting, The fire pit with seasoned firewood was a big hit for our group, All the beds were comfortable, The bedrooms were large and comfortable, The baths were clean, modern & large and The location to "What to do in Cambridge" is only 7-10 miles away. We made prearrangements: Richardson Maritime Museum to have a guided tour with David Williams on Friday and Spocott Windmill with George Radcliff. Both of these tours were fascinating. Our weekend was 5-Stars.

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit
Our family had such a great time staying at MJ's place last year that we came back again this summer. As before, we all loved the view, pool, firepit, grilling on the deck, and walking down to the neighborhood beach. The house was very clean and the kitchen was well-stocked. All the beds were comfortable, and all bedrooms had well-functioning blinds/shades, which is really helpful when putting younger kids to bed. The lower level bathroom had been renovated since our last stay which was a great bonus. We are looking forward to returning next summer!

South River Beach Front House
I stayed here the week of my wedding and it was absolutely perfect! From waking up each morning to have coffee on the dock with my pups and husband, to the beautiful views from each room in the house, we truly had a lovely time and chose the right Airbnb for such a special week in our lives.

Waterfront Farmhouse Meets Modern Luxury
Beautiful house! Clean, well maintained, and exactly as described. The host was easy to communicate with and very responsive throughout our stay. The space felt comfortable and welcoming, and everything we needed was thoughtfully provided. We had a great experience and would definitely love to come back!

Family Friendly: Hot Tub, Grill, Pool & More!
This was one of the most well equipped houses I have ever stayed in. The hosts were very easy to communicate with and responded quickly to each contact. I highly recommend this place!!

Casa Blanca—where luxury meets tranquility
My stay at this Airbnb was absolutely wonderful! The space was beautifully decorated, clean, and had all the amenities I could have needed. The hosts were incredibly responsive and helpful from booking to check-out, answering all my questions promptly. I highly recommend this Airbnb to anyone looking for a relaxing and memorable getaway. I will definitely be back, in fact, I'm already exploring availability!
Apartment rentals with a pool

Beach Paradise 202-Downtown Luxury Condo Bay View
Bao was prompt at responding to questions. The home was immaculately clean and much more spacious than appeared in the photos. The price was worth what we paid. My family and I were quite comfortable and we appreciated the starter items included with the rental. There were ample cooking utensils and the appliances were clean and in excellent condition. We travelled from out of state and brought a suitcase with our own linen. Not ideal, but this was a much more financially prudent option than paying the linen providers $190.00 for sheets and towels. Overall, we thoroughly enjoyed our stay at Bao’s rental. We were close to restaurants and the beach and had a view of the water. We highly recommend this property.

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.

🏖 *Ocean *Ocean *Ocean* 🏖 Beautiful Condo!!
A mini vacation should be free of headaches and life's hustle, Although, That was not the case at the condo. The place was not cleaned properly, However this is the cleaners not Adam. When something is presented at a certain level, it should be truthful

Prime Condo North OC 2 Blocks to Beach w/ Pool
Richard was extremely responsive and easy to communicate with. He went over and beyond! The place was very clean. It was walkable to a private beach and nearby ice cream, coffee, and restaurants. A quick walk to the bus station for an easy and cheap ride to the boardwalk. Loved the balcony and view of the pool. Easy parking also! Lots of parking available. Everything was very clean and smelled amazing too. Would absolutely recommend this home, we hope to stay here again in the future!

🌊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! 😊

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom
I would 100% recommend Rodrigo’s condo! Such a quick walk to the beach and the amenities were great especially with a toddler. I liked how it wasn’t directly on the boardwalk, it made it feel like an area guided more towards families. The private laundry room was a great bonus too as well as being a corner unit to leave your beach items outside as well. I liked how there were items for children in the condo such as a pack and play and children’s plates etc. we didn’t need these items, but it was nice to see that it was included for those with children that may have forgotten certain items. Rodrigo was a great host as he was very quick to respond and was very helpful as well as just checking in to see that everything went smoothly and if we needed anything. I would definitely book here again for the next time we visit Ocean City, Maryland!!!!!

Getaway in Ocean Pines
Selena was thorough, clear check in/check out instructions, with alot of recommendations included in the home. The condo was very clean & fully stocked with whatever we may need. Very, very peaceful & cozy!! We all slept so well, as if we were home in our own space. Not far from the boardwalk & lots of restaurants nearby. I would definitely recommend & stay again. Thank you Selena for your hospitality & for making your space feel like our “home away from home”!!

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.
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