Vacation rentals with a pool in St. Mary&#x27;s County

A private salt-water pool is featured, surrounded by lush greenery. The pool's shimmering blue water reflects the sunlight, while a smooth entry step leads into the inviting space. A safety fence encloses the area, ensuring guest privacy.

4.92 out of 5 average rating, 79 reviews

Spacious and private waterfront, sleeps 10

MichaelRating, 5 stars3 weeks ago

The location for this house is beautiful! We loved the private dock and spacious backyard. We stayed in late March so it was a bit cold some days but we still had a great time using the provided Kayaks and sitting on the dock and watching the beautiful surroundings. The location was perfect to have some s'mores nights around the firepit. The hosts were VERY responsive. The few times I had questions they replied within minutes and were very accomodating with our requests. They were very proactive with instructions and generously mentioned a foldable crib for the infant in our group - although we had our own that we used. The kitchen had all of the dinnerware and cookware that we needed for the meals that we made. The living areas were open and inviting. It was perfect for our group. One thing to watch for is the very steep driveway. It took a few times to get used to. We would definitely stay there again when we visit our family in the area.

4.99 out of 5 average rating, 150 reviews

Beach Please! River cottage w/private beach & dock

AudreyRating, 5 stars2 weeks ago

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.

A serene sunset view over the Potomac River is captured, with gentle reflections shimmering on the water's surface. Silhouette of tall grasses frame the image in the foreground, while silhouettes of docks are visible along the shoreline.

4.93 out of 5 average rating, 45 reviews

Brigadoon, the BRAND NEW Waterfront Haven

IvoryRating, 5 stars6 days ago

Our stay at this beach house was absolutely unforgettable! From the moment we arrived, we could tell how much thought and care had gone into making this home a perfect getaway. The mud room was such a thoughtful addition—for our dogs and kids after fun outdoor adventures. The screened porch quickly became our favorite spot to relax, offering a peaceful space to unwind, read, and drink coffee while enjoying the breeze. The direct access to both the private beach and the river was amazing. Whether we were digging into the sand by the waves or exploring the waters, the convenience was unbeatable. The water toys, especially the kayaks, were a big hit with the kids—hours of joyful paddling and laughter made for great memories. The kitchen amenities were phenomenal! It was stocked with everything we needed to cook delicious meals, making dining in as enjoyable as eating out. We couldn’t have asked for a better place for our family vacation! Hands down one of the top places we stayed!

An aerial view of the house showcases a spacious deck with comfortable seating, surrounded by a railing. A dock extends into the water, equipped with a covered boat lift. Lush greenery borders the property, providing a serene backdrop.

4.97 out of 5 average rating, 87 reviews

Waterfront Gem: Dock, Hot Tub, Beach, Pool, Kayaks

NoraRating, 5 stars3 months ago

Andrea was extremely proactive and responsive to our questions, even reaching out ahead of time to make sure we were aware of work being done and arranged for late check-out, a huge help for our group. The local recommendations were really appreciated, and it's such a beautiful location along the water.

The backyard features a private pool surrounded by landscaped gardens and a variety of seating areas. Flowering plants add color to the foreground, while lounge chairs line the poolside. The house and trees are visible in the background, complementing the serene setting.

5 out of 5 average rating, 15 reviews

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

DeniseRating, 5 stars5 months ago

The area and view are beautiful and the home's decor is welcoming. The home was very comfortable for our family group and had a VERY well-stocked kitchen. The master bed was VERY comfortable as were the rest of the beds. My husband and I slept well. We all felt at home. MJ was very responsive when I had questions and communicated about the property in clear, concise language. The host provided many outdoor recreation opportunities, which included paddleboards, kayaks, and life jackets. There was a nice sized pool but we were visiting out of season so we did not use it. The exercise room downstairs has a lot of equipment. We all enjoyed our time together. Our family is asking to come back again next year. Thanks for a great stay!

4.93 out of 5 average rating, 200 reviews

The Glebe

LynnRating, 5 stars1 month ago

Excellent stay at RivahLife! The views were spectacular and the home was exactly as described. Easy to find with lots of stuff for the kids and adults. Looking forward to returning during the warmer months as the fishing, boating, and swimming would be more desirable. Thanks for the high chair and portable crib. Those things really help when traveling with kids.

Superhost

A serene view of a private beach meets the calm waters of the bay under a clear blue sky. Gentle waves lap at the sandy shore, with a wooden dock extending into the water. Soft grasses frame the beach area, contributing to the tranquil atmosphere.

Villa in Montross

4.85 out of 5 average rating, 95 reviews

Beach Retreat

CharlotteRating, 5 stars1 month ago

Beautiful spot and gracious host. This was exactly as described, had all the amenities we could want, and Frank was incredibly clear in instructions, responsive and organized. We spent a lovely week in a gorgeous, soothing location with our pup — fully refreshed after only 4.5 days!

4.97 out of 5 average rating, 37 reviews

An open living space features a modern kitchen with stainless steel appliances and white cabinetry. A wooden dining table with light-colored chairs is positioned centrally, accompanied by a cozy seating area. Large windows provide natural light and a view of the adjoining four-season porch.

Cottage in Montross

Harbor Cottage

KimRating, 5 stars1 month ago

The home and property were peaceful and quiet. We especially loved the spacious, (all weather) sunny enclosed porch. The kitchen and family room were comfy and had everything we needed. We walked the neighborhood with our dogs and the beach was beautiful as well as relaxing. Such a wonderful weekend get away.

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What guests are saying

Waterfront+DOCK+Beach+Kayak+Paddlebd+Arcade

5 out of 5 average rating, 29 reviews8 months ago

Beautiful location on the water with a lovely dock and the ability to do SUP and walk to a small bit of local beach. Quiet neighborhood though neighbors driveway light is too bright. Enclosed porch area with good AC is a great place to sit and watch the world go by. Kitchen has all you need. Bedrooms are fine but would be a bit better with nicer pillows and mattress toppers. This is a remote spot in that there are no restaurants or coffee shops to walk to. Everything is a drive. The community pool and tennis courts have to be driven to - not walkable. While nice to have them, they are a bit run down. Regardless we still used and enjoyed them. Overall I certainly recommend it and the hosts were very accommodating and responsive.

Home in Montross

What guests are saying

The Marina Oasis in Taylors Island

4.7 out of 5 average rating, 82 reviews32 months ago

It was a comfy stay in a beautiful marinia. The house was clean and the beds were soft. It did well for me and my 4 kids who each had their own bed. The landscape of the place and the sunsets were great! It was quite, tranquil with beautiful warm and sunny days. I would go back. Very easy check in and out.A lot to do in the area.

Home in Taylors Island

What guests are saying

Idyllic Montross Vacation Rental Home w/ Views

4.85 out of 5 average rating, 20 reviews6 months ago

We really enjoyed the stay at the River House. We are a repeat customer and the house did not disappoint us. The host is very gracious and everything is just as the website has it listed. We enjoyed the amenities, lots of videos, games and the hottub. There is a short walk to the beach which we visited twice a day. We loved every minute of it! Thank you!

Home in Montross

What guests are saying

Living Water Farm

4.95 out of 5 average rating, 39 reviews1 month ago

Fantastic place. Welcoming. They thought of everything and more. Linens. Coffee. Electric fireplace. Laundry with iron and board. Toiletries. Glorious fragrance. High ceilings for a basement! Can’t say enough nice things about the place inside and out. Coming back as soon as I can.

Apartment in Mechanicsville

What guests are saying

Waterfront, heated pool, views

4.67 out of 5 average rating, 3 reviews3 days ago

We had a fantastic stay at this amazing home! The heated pool was a huge hit with everyone and made the trip extra special. The house was clean, comfortable, and had everything we needed. The lake was really nice! We enjoyed fishing from the dock and having views of the lake from all angels of the house and from the dock. We’re especially grateful to the host for being so accommodating and flexible throughout our stay, it made everything smooth and stress-free. Highly recommend!

Home in Lusby

What guests are saying

Chesapeake waterfront farmhouse w pool nr Solomons

4 out of 5 average rating, 3 reviews9 months ago

This farm house was beautiful and full of character. Didi was very responsive and helpful when we needed it. The instructions for operating the pool were spot on, and the pool was by far the favorite thing about this house for our kids and us. The house was well stocked with everything we needed and more. We were pleasantly surprised that there was a piano in the main living area. My kids were playing consistently. There were so many games, DVD's to watch and a full screen projector that we could stream movies too. Sitting on the porch watching the Osprey nest was another favorite. There were 11 of us and there was plenty of sleeping spaces and bathrooms for all of us. We were there during an extreme heat wave and the house stayed cool and comfortable with the air conditioners. We loved the kayaks and did take them out but since it was jellyfish season we couldn't swim in the river water. We explored the local recommendations that Didi sent to us. We had a wonderful time.

Home in Lusby

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Popular amenities for St. Mary's County rentals with a pool

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Pool

Free parking on premises

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House rentals with a pool

A spacious bedroom features a large wooden bed with a light comforter and decorative pillows. Two leather benches are positioned at the foot of the bed. Natural light fills the room through large windows adorned with wooden shades, and a ceiling fan adds to the comfort.

4.99 out of 5 average rating, 94 reviews

Waterfront+Kayaks l Beach+Pool l Gameroom+Firepit

ShikufaRating, 5 stars2 weeks ago

We had an amazing trip and truly enjoyed every moment of our stay! The house was absolutely perfect clean, cozy, and had everything we needed. From the comfortable beds to the well-stocked kitchen and relaxing outdoor space, it was the perfect home away from home. We appreciated all the thoughtful touches and would definitely love to come back. Highly recommend!

A bright sunroom features large windows offering scenic water views. Four teal armchairs encircle a round wooden table, complemented by a textured area rug. A selection of board games is visible on a nearby shelf, creating an inviting space for relaxation and connection.

4.98 out of 5 average rating, 41 reviews

Game-Themed Waterfront Fun! Dock-Boats-King Suite

NiyaRating, 5 stars3 weeks ago

I stayed here with my three kids for a little getaway, and we had the best time. The place was super clean and spacious, and the modern decor and finishes were clearly chosen with care—it just felt really good to be there. The game rooms were such a fun touch, each with its own theme, and the kids were obsessed! One of our favorite parts was the scavenger hunt—it was such a fun and unexpected surprise, and it gave us a memory we’ll definitely hold onto. The host was incredibly kind, polite, and respectful. Overall, it was just a great experience and a really special trip with my kids.

Superhost

A two-story waterfront home is showcased, featuring a spacious deck and a heated pool. Lush greenery lines the gravel pathway, and well-maintained landscaping surrounds the property. Clear blue skies reflect a serene atmosphere, while the water glimmers nearby, enhancing the tranquil setting.

Home in Lottsburg

4.96 out of 5 average rating, 69 reviews

Heron Harbor

DianaRating, 5 stars32 months ago

All I can say is WOW! We were blown away at the beauty of the home AND the view! Relaxing and peaceful. The pool was to die for and Kathleen was one of the best hosts I’ve ever had in all our air bnb travel!!! Will definitely return AND will check out her other properties in the future. Thank you to Kathleen and her staff/team!!

A spacious exterior view of a wooded home is depicted, showcasing a gravel driveway leading to a welcoming entrance. Large glass doors provide a view into the interior, while lush greenery surrounds the property, enhancing the natural setting.

5 out of 5 average rating, 6 reviews

Newly Renovated River Retreat w/Dock and Pool

JamieRating, 5 stars1 month ago

Such a beautiful home with everything stocked to host a family gathering. This kitchen had everything included so that I could cook homemade pasta and a feast for a large family gathering. And to boot, the endless pool hot tub is an awesome workout! They were also very patient and responsive to our needs. Thank you!!

A tranquil pool area is surrounded by greenery, featuring a blue in-ground pool with clear water. A concrete deck provides space for lounge chairs and an umbrella. A decorative float rests on the water while a shaded seating area is visible in the background.

5 out of 5 average rating, 3 reviews

Bliss By The Bay Chalet

CamRating, 5 stars7 months ago

Dana's house, made me feel right at home. Very peaceful. Not noisey, people were extremely nice. Her pool was also very nice, secluded and private. Very nice to be able to swim in a deep pool. The food recommendations were amazing. Both restaurants that I tried were absolutely delicious and not far at all. The distance from both beaches are not far at all. So nice to be able to just take a beach chair, and sit out by the water. Dana was a wonderful hostess, and her house is definitely a gem. If you want a little getaway/staycation, choose her house. You will not be disappointed.