Vacation rentals with a pool in Queen Anne's County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Queen Anne's County rentals with a pool

House rentals with a pool

Guest favorite
The outdoor scene showcases a fenced-in area with a circular above-ground pool adjacent to a wooden deck. Lush green grass surrounds the pool area, with landscaped flower beds and trees in the background, creating a tranquil and spacious environment.
Home in Rock Hall
4.95 out of 5 average rating, 38 reviews

Rockfish Keeper

Mary JaneRating, 5 stars1 month ago
It was a great stay after a long day roaming around Washington DC and Maryland. The accommodation was clean and nicely decorated with very inspiring words of wisdom providing a cozy and comfortable retreat throughout our stay. Kelly has been very informative and detailed on the instructions to help us on a very smooth check in and check out process. The location was fantastic and quiet neighborhood. Overall, we had a wonderful time and would highly recommend this place to anyone looking for a memorable Airbnb experience!"
Top guest favorite
A clear swimming pool reflects the overcast sky and surrounding buildings. Multiple white lounge chairs are arranged around the pool, accompanied by blue umbrellas offering shade. The pool area is enclosed by a low fence, creating a serene atmosphere for relaxation.
Home in Rock Hall
5 out of 5 average rating, 15 reviews

The Mariner's House

ErinRating, 5 stars1 month ago
Wonderful property with lots of amenities!
Top guest favorite
The exterior of the house features a combination of natural stone and shingle siding. A well-maintained garden with flowering shrubs borders the walkway. A small porch is visible, providing access to the entrance, all under a clear blue sky.
Home in Stevensville
5 out of 5 average rating, 5 reviews

Bay Bliss House

IanRating, 5 stars1 week ago
Beautiful property and well maintained. Unique views and plenty to do when the weather is not so good. Great proximity to Annapolis and the Eastern Shore and plenty of great dining spots on the water.
Guest favorite
A two-story home is seen from the perspective of a patio area, featuring a large saltwater pool in the foreground. Lounge chairs are arranged around the pool, and string lights are hung overhead. A garden area with plants borders the pool, adding greenery to the scene.
Home in Church Hill
4.89 out of 5 average rating, 53 reviews

Private Peaceful Waterfront House w/ Pool, Hot Tub

LenaRating, 5 stars11 months ago
This was our 2nd year at Peaceful Waters. It is indeed just that! Peaceful! Perfect and beautiful location. Everything needed is there to assure a wonderful carefree stay. The place is well stocked, clean and is just as it reads and appears! My group of 16 loved the place AGAIN this year. Hopefully, planning to go back next year. Matthew and Rose are great to work with! ❤️
Superhost
A private pool is centrally located, surrounded by a well-kept grassy yard. Lounge chairs are positioned around the pool, providing relaxation options. The two-story cottage is visible in the background, along with a shaded area and trees that create a serene setting.
Home in Stevensville
4.45 out of 5 average rating, 20 reviews

Private Pool, Bay Views near Kentmorr Bar & Beach

DeniseRating, 5 stars11 months ago
Had a wonderful time with my family
Superhost
The home features a welcoming exterior illuminated by warm outdoor lighting, showcasing large windows and a spacious deck with comfortable seating. A pool and spa, glistening in green hues, are surrounded by lush landscaping, creating a serene evening atmosphere.
Home in Saint Michaels
4.58 out of 5 average rating, 12 reviews

10 Minutes to St. Michaels with a Private Pool

SarahRating, 5 stars1 week ago
This home gave us something we hadn’t experienced before: a vacation with two small children that actually felt like a vacation! From the moment we arrived, we were blown away by how perfectly suited the home is for families with young kids. The pool has a shallow platform area that our toddlers could safely enjoy, and the expansive, beautifully maintained yard gave them plenty of space to run and play freely along with a swing and hammock. Inside, the house is just as exceptional. The layout is thoughtfully designed, with a separate bedroom wing that allowed us to put the kids to bed and then relax in the evenings without worrying about noise. Every detail felt intentional and welcoming, and the water views were absolutely stunning. The home is just a short drive from the charming town of St. Michael’s, which we loved exploring. This trip was such a joy for our entire family, and we’re already talking about when we can come back. Highly, highly recommend!
Top guest favorite
The outdoor pool area features a spacious salt-water pool surrounded by a stone patio. Comfortable seating is arranged on either side, with colorful landscape visible in the background and an umbrella providing shade. The skyline is adorned with hues of sunset across the bay.
Home in Stevensville
5 out of 5 average rating, 17 reviews

Bayside Escape

JohnRating, 5 stars5 days ago
Our family of 3 had an amazing vacation on our 4 day stay. It was so peaceful and relaxing. The place was exceptionally clean and organized with everything needed. Amazing views on the water and pool was great. We had some rainy weather but still managed enough dry time to enjoy the pool and outdoors
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, 65 reviews

The Peaceful Getaway (with private pool & hot tub)

AnnaRating, 5 stars1 day ago
Great stay, comfortable beds, nice TV, loved the pool. Had an excellent time and will rebook next time I'm in the area

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