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

Bright/Cozy 4BR Home w/ Heated POOL Near MGM & DC
Staying at Luam's place was great! The house looks exactly as it is listed. We wish the pool would have been available for use :( but all other amenities and accommodations were exceptional! The house came with a fully stocked kitchen perfect for cooking a great meal. The house was spacious and there was plenty of room for all of my guests. There could be more mirrors in the house as the only mirrors were in the bathrooms and 1 large mirror in the living room and the beds were slightly hard but that did not take away from how amazing the house was. It was 20 minutes from DC in a quiet area. The perfect home away from home. Thanks, Luam for being so responsive and providing easy check-in instructions. We would definitely stay again if in the area.

Mins to Annapolis from Waterfront home Pool, Pier
House owners were extremely responsive and informative. House was well stocked , and a great location and view made the stay even better.

Bay Breeze Retreat
Beautiful house and property, great location, and the host was super responsive. Hope to return sometime soon.

Modern Bay Dream
Rick was very supportive and his communication was superb. Great host with a beautiful cozy home. 5 star all across the board.

Beach Please! River cottage w/private beach & dock
This was our second stay at Beach Please and it was just as delightful as the first! The house was again squeaky clean, thoughtfully decorated and had plenty of room for our multi-generational family to spread out. Grandparents appreciated the first floor master bedroom and kiddos loved the game room, and the crafts and puzzles upstairs. The neighborhood is peaceful and cozy, with beautiful views in every direction. The addition of the acoustic guitar for songs by the firepit was a major plus, as our ten year old is a music lover and almost brought her own. We had a great stay and would recommend this AirBnB to anyone! Grab a week (or two) and don't think twice.

The Little Gypsy BoHome
The place was perfect, clean, homey, comfortable and really unique. Loved the pool, cold plunge, sauna, screen porch. We had everything we needed from fresh flowers and cookies to convenient multiple charging stations by the beds. Loved the outdoor lighting and overall coziness of this place. Quiet and peaceful, sounds of the water lapping the shore, beautiful place to drink morning coffee and watch the sunrise. Also found some great sea glass on the beach!! Love, love, loved staying here :)

Historic Rousby Hall, Waterfront, Patuxent River
What a lovely stay! Incredibly charming home with such hospitable hosts. Our group felt comfortable and relaxed. Picturesque environment.

Spacious Retreat w/ Pool, Washington DC Area
We enjoyed the house and its amenities. The beds were super comfy, perfect combination of firm and soft, with a variety of pillow types to choose from. There was plenty of hot water for 6 showers every morning, and we were all getting ready about the same time. When the dryer squealed and I notified Ruben, he immediately offered to send a repairman with our convenience in mind. He responded quickly to any questions from the very beginning of the reservation throughout our stay. My sister especially liked having a ceiling fan in the master suite. My 92-year-old mother was thrilled with a ground floor bedroom and a half bath right next door. We often gathered around the table in the kitchen area to make our plans, and though we didn't cook much we appreciated that the kitchen was equipped with everything we needed. The quiet neighborhood made us feel safe and let us sleep well.
Condo rentals with a pool

Rooftop bay and river views
House was great with space for everyone whether we gathered for a meal or game wanted to spread out. Super easy walk to the beach and boardwalk. GREAT coffee shop and a few gems of restaurants and shops-we were definitely there in off season and the town was not fully opened - lots of opportunity in the town and lots of places getting opened for the season! Would be a great place for a quick summer getaway

National Harbor 2bdrm condo near DC, Gaylord, MGM
Wonderful experience! The accommodations were just as described, well kept and comfortable, and the location was perfect. Thanks to Janee as well for answering all my questions and making for a seamless process!

The Fountains condo one bedroom 2 level apartment
The host was more than accommodating and the condo Is exactly as pictured . Great stay

Charming Annapolis Waterfront Condo
We really enjoyed our stay! The place was clean, comfy, and had everything we needed. Jared was super responsive and helpful. I highly recommend.

Cozy Annapolis Condo
Host gave an accurate description. Also, gave clear and easy instructions for checking in to condo. Had everything we needed. Comfortable beds! Would highly recommend if you're visiting the Annapolis area.

Lovely 1-bedroom condo w/ 2 parking spots near DC
I definitely loved this home soooo spotless felt right at home. You might hear people walking here and there BUT it’s not an all the time thing, other than that it’s so peaceful. Kitchen is beautiful and has all the spices you kinda need if you wanna cook, bed was sooooooo comfortable and the living room was so inviting. It’s close to food spots banks grocery stores, etc. I’m definitely booking again.

Newly Renovated 1-Bedroom on Spa Creek
To say this place was perfect is an understatement! I didn’t want to leave! The apartment is equipped with everything you need. Some highlights: a location near the water with great views, extremely clean and beautifully decorated, easy parking and walkable to EVERYTHING! Marie is the perfect host - proactive with all the information and reachable with any questions! Even better, the per night cost is about half that of a hotel in town! There is no doubt I will be staying here again on my next Annapolis adventure. :)

Modern Apartments available at National Harbor
I cannot say enough about this property or Kenny. It was an extremely busy for me as it was my daughter’s wedding. Kenny made the check-in, stay, and check out easy for me, which is just what I needed. He checked on us frequently, but not too much. He was very responsive to a few questions that I had. The place was clean, well furnished, and a really fun area to stay in. I highly recommend Kenny and this property!
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- Nationals Park
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