Vacation rentals with a pool in Maryland

Find and book unique homes with a pool on Airbnb

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Popular amenities for Maryland rentals with a pool

House rentals with a pool

Top guest favorite
The swimming pool is illuminated at night, casting a soft light on the water's surface. Surrounding trees create a serene backdrop, while a dog walks along the poolside. An orange traffic cone is positioned in the foreground.
Home in Sabillasville
4.93 out of 5 average rating, 121 reviews

Stoney Spring Overlook

TracyRating, 5 stars1 week ago
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!
Superhost
A refreshing saltwater pool is framed by comfortable lounge chairs in vibrant red and blue. A large grassy area is visible beyond the pool, leading to serene waterfront views under a clear blue sky, complemented by a tree providing shade.
Home in Queenstown
4.81 out of 5 average rating, 157 reviews

Bay Breeze Retreat

TobyRating, 5 stars1 month ago
Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.
Top guest favorite
A tranquil view of the private pool framed by potted plants featuring colorful flowers. The pool area extends towards a serene body of water, surrounded by trees. The distant shore is visible, enhancing the natural beauty of the setting.
Home in Lusby
5 out of 5 average rating, 19 reviews

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

AlanRating, 5 stars1 week ago
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!
Guest favorite
An inviting outdoor space features a private pool surrounded by a patio area, with ample lounging options under a shaded umbrella. The indoor movie theater displays a large screen with surrounding comfortable seating, while a vibrant game room showcases a foosball table and neon lighting.
Home in Salisbury
4.9 out of 5 average rating, 62 reviews

Bury Oasis: Pool, Hottub, Movie Theatre, Game Room

ChristineRating, 5 stars3 days ago
We cannot say enough good things about this home. It had everything we could have wished for! Our family of 11 enjoyed every moment and wished we didn’t have to leave. The house was immaculate. The host (Caleb) was so quick to respond to our messages and even popped by to help us figure out the surround sound one evening. We cooked and ate every meal at the house and had all kinds of things to do just minutes from the house (disc golf, golf, pickle ball, a zoo, shopping). We even decided to forego our plans to go to the beach because why would we go when they have their amazing private pool. We were entertained from morning to night with all the games and surround sound movie room. There was NOTHING we didn’t love about this home. Thank you, Glen and Caleb! I would give you 10 stars if I could!
Guest favorite
A serene view of the Chesapeake Bay is captured from the backyard, featuring a pool surrounded by green lawn. Towering trees provide shade, while a patterned stone patio is visible in the foreground, enhancing the outdoor atmosphere.
Home in Chester
4.95 out of 5 average rating, 96 reviews

Waterfront Farmhouse Meets Modern Luxury

EricaRating, 5 stars6 days ago
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!
Superhost
A stately brick building is set amidst lush greenery, featuring a symmetrical façade with large windows and a striking red front door. Well-maintained lawn and trees frame the property, enhancing its welcoming presence.
Home in Port Republic
4.78 out of 5 average rating, 23 reviews

Family Friendly: Hot Tub, Grill, Pool & More!

TakishaRating, 5 stars3 weeks ago
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!!
Superhost
A shimmering in-ground pool is surrounded by a spacious deck featuring lounge chairs. A shaded patio area can be seen nearby, offering seating and an umbrella. Lush greenery provides privacy, while a wooden fence encloses the pool area, blending with the natural surroundings.
Home in Millington
4.86 out of 5 average rating, 66 reviews

The Peaceful Getaway (with private pool & hot tub)

AnnaRating, 5 stars3 days ago
Great stay, comfortable beds, nice TV, loved the pool. Had an excellent time and will rebook next time I'm in the area
Guest favorite
A spacious backyard features a private swimming pool surrounded by a patio. Lounge chairs are positioned for relaxation, with a small shed visible in the corner. A two-story house stands in the background, showcasing multiple windows that allow natural light.
Home in Fort Washington
4.88 out of 5 average rating, 52 reviews

Spacious Retreat w/ Pool, Washington DC Area

DianaRating, 5 stars2 weeks ago
Had the pleasure of staying at Ruben’s with my friends for a girls’ getaway, and wow—did we all love this place! It was spotless, spacious, and had everything we needed for a relaxing trip. The host was incredibly responsive and made everything so easy. We’re already planning to stay here again!

Condo rentals with a pool

Guest favorite
A community pool is visible behind the building, surrounded by a white fence. Lounge chairs are placed around the pool area, and a small structure is nearby, possibly housing pool equipment. The building features multiple windows and an exterior painted in a light gray color.
Condo in Ocean City
4.9 out of 5 average rating, 152 reviews

Beach Paradise 202-Downtown Luxury Condo Bay View

JustinRating, 5 stars3 weeks ago
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.
Guest favorite
A light-filled living area features a soft, neutral-toned sectional sofa facing a wooden coffee table. Floor-to-ceiling windows showcase ocean views, with sunlight reflecting off the water. A flat-screen TV is mounted on a wooden entertainment unit, complementing the room's modern design.
Condo in Ocean City
4.91 out of 5 average rating, 310 reviews

Oceanfront Family Oasis: Pool, Beach & Parking!

JasonRating, 5 stars1 month ago
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.
Top guest favorite
An oceanfront pool is visible in the foreground, featuring a circular design with wooden decking surrounding it. The clear blue water reflects the sunlight, offering a serene view of the ocean and sandy beach in the distance.
Condo in Ocean City
4.99 out of 5 average rating, 221 reviews

Cozy oceanfront condo with stunning ocean views

NickRating, 5 stars5 days ago
We had a great stay! The condo was exactly as described and pictured. Everything was well kept and clean. The location was perfect as there was lots to do but wasn’t overly crowded. We would definitely stay here again.
Superhost
A spacious living area features a comfortable gray sectional sofa adorned with colorful cushions. An inviting lamp sits on a coffee table, while the light beige walls complement the tiled flooring. The open layout connects to the kitchen and dining space in the background.
Condo in Ocean City
4.83 out of 5 average rating, 282 reviews

🏖 *Ocean *Ocean *Ocean* 🏖 Beautiful Condo!!

ErinRating, 5 stars3 days ago
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!!
Guest favorite
The outdoor pool area features a large, sparkling blue pool surrounded by a sunbathing deck. Multiple lounge chairs are placed along the edges, with umbrellas offering shaded spots. Lush greenery and a fence create a tranquil environment, ideal for relaxation.
Condo in Ocean City
4.9 out of 5 average rating, 204 reviews

Prime Condo North OC 2 Blocks to Beach w/ Pool

AngelinaRating, 5 stars1 week ago
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!
Superhost
A sunlit indoor lounge area is surrounded by large windows, offering a view of the indoor pool. Rattan furniture with tropical-patterned cushions is arranged around a low table. Decorative plants enhance the green ambiance, contributing to a relaxing environment.
Condo in Ocean City
4.87 out of 5 average rating, 199 reviews

🌊Oceanfront studio w/ amazing views & amenities🏖

VeronicaRating, 5 stars4 days ago
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! 😊
Guest favorite
An open-concept living and dining area features a wooden dining table set for six, complemented by modern chairs. A comfortable seating arrangement with light-colored couches is situated near large windows, offering views of the surrounding area. A mounted TV and decorative elements enhance the space.
Condo in Ocean City
4.95 out of 5 average rating, 108 reviews

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom

BrittanyRating, 5 stars1 week ago
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!!!!!
Top guest favorite
The spacious pool area is surrounded by shaded umbrellas and lounge chairs. A large group of individuals enjoys the water, with a vibrant blue sky above. Steps lead into the pool, providing easy access for guests. Lush greenery frames the scene, enhancing the sense of relaxation.
Condo in Ocean Pines
4.96 out of 5 average rating, 171 reviews

Getaway in Ocean Pines

LashenaRating, 5 stars3 days ago
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”!!

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