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

4.89 out of 5 average rating, 57 reviews

Aerial view of a home with a fenced swimming pool, surrounded by lush green grass. The pool features a clear blue water, and several lounge chairs are positioned around its edge. Steps lead from the house to the outdoor area, enhancing accessibility to the pool.

Home in Ridge

Waterfront Paradise with a Private Pool

Set on three acres of spectacular waterfront property, there’s everything you need to escape – a dock, a fire pit, crab traps, kayaks, bikes and a POOL. Next door: 20 acres of unkempt forest where bald eagles fly. The pool is closed until end of April and is not heated. The home is warm, unpretentious, with a minimalist approach to décor but a stocked kitchen for those who love to cook. Amenities: a HDTV with premium channels, high speed internet, a ping pong table, lawn croquet and more.

4.98 out of 5 average rating, 54 reviews

An outdoor pool is seen under clear blue skies, surrounded by a paved area. Sun loungers are positioned nearby, with trees lining the background. The calm water reflects sunlight, creating a serene atmosphere for relaxation.

Villa in Hague

Sea Glass Paradise

The Seaglass Paradise is an amazing river front property. Pets are welcome! Relax on the white sands with family and friends. Fish right off the private dock, build a fire on the beach at night, and bring your boat ! Boat slips are available at the Marina . Access to the marina pool included in your stay. A Beautiful year round Vacation Home! Coastal 4BR Escape: Families-Friends-Pets Welcome! Fire Pit, Boat Slips & White Sands - Vacation: ON! Family-Fun Seaglass Home Steps from Chesapeake Bay

A cozy enclosed porch features comfortable lounge chairs with soft cushions. The space is illuminated by string lights and showcases a decorative rug, while large windows provide views of the outdoor environment. Green plants add a fresh touch to the inviting atmosphere.

4.94 out of 5 average rating, 36 reviews

Retro Retreat w/ Beaches, Pool + Tennis + Firepit

A quintessential 1970s house, characterized by bold patterns, earthy color schemes, and avocado green appliances. Geometric wallpaper and low-slung furniture dominate the living spaces. Disco-era charm extends to vibrant bedrooms; backyard boasts a lighted firepit area. This nostalgic retreat immerses guests in the groovy aesthetics of the 70s, providing a retro-cool escape. 4 beaches, a pool, and tennis. Close to Westmoreland State Pk, Colonial Beach, art galleries, great restaurants, and more.

5 out of 5 average rating, 5 reviews

A sleek white boat is docked at a marina, showcasing a well-maintained exterior. The boat features multiple windows, and a small upper deck is visible. The calm water surrounds the vessel, reflecting the overcast sky and nearby sailboats, captured in a serene moment.

Boat in Kinsale

Spend the Night on the River

Experience the charming town of Kinsale with a home base in the heart of it all. This boat offers comfortable & spacious accommodations with all the perks of the marina - pool, tennis court, seasonal bar, kayaks - right outside your cabin. Located on the Yeocomico River, The Slips Marina features a recently updated clubhouse where you can hang out, shower, enjoy the roof deck bar & many special events throughout the year. Note the boat does not have a usable bathroom, but clubhouse is nearby.

A lone swan glides across calm water, creating gentle ripples. The bird's white feathers contrast against the soft blue of the lake. Surrounding the swan, large, round stones edge the water's surface, providing a natural border to the serene scene.

5 out of 5 average rating, 14 reviews

Water View Cozy Getaway- beach/Kayak/fishing/pool

Welcome to your ultimate waterfront community getaway! Our charming and cozy house is newly built 4 bedrooms and 4.5 bathrooms and 3 minutes Walking distance to the public beach, making it the perfect retreat for anyone looking to enjoy modern amenities in a serene and tranquil setting. Whether you're looking for a romantic getaway, a family vacation, or a peaceful retreat, our house offers a truly unique and unforgettable experience. We can't wait to welcome you to your home away from home!

4.99 out of 5 average rating, 155 reviews

Beach Please! River cottage w/private beach & dock

Come unwind at "Beach, Please!" Our renovated cottage on the river with a private beach and dock is waiting for you! What's there to do? There's boating, fishing, crabbing, bird watching, tanning, and hammock-napping. Need more? Ok, antique shops, breweries, wineries, live music, crab boils and oyster fests. Still need more? Cornhole, can jam, horseshoes, hiking, and swimming and tennis at the community pool. That's not all, so just trust us - you will LOVE your time in Montross, Virginia!

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.

4.94 out of 5 average rating, 51 reviews

Brigadoon, the BRAND NEW Waterfront Haven

Relax with your whole family at our peaceful home. Discover an oasis of serenity at this stunning 3-bedroom, 2.5-bath retreat boasting panoramic views of the Potomac River from every window. Marvel at breathtaking sunrises and sunsets, from your own private beach, immersing yourself in the tranquility of the landscape. Situated just 2-3 hours from the Washington, DC Metro Area, 2 hours from Charlottesville, and 1 hour from Richmond, this haven offers an easy escape into nature's embrace.

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.

5 out of 5 average rating, 16 reviews

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

Welcome to our waterfront paradise overlooking the Chesapeake Bay! Experience comfort and tranquility at this extraordinary retreat, where breathtaking views and unforgettable memories await you. This serene beachfront property is little over an hour from DC & Northern Virginia, and about 90 minutes from Baltimore. With private pool, fire pit, kayaks, paddle boards, pingpong, weights & workout equipment, it's a perfect place to recharge and make memories with family and friends.

4.92 out of 5 average rating, 207 reviews

The Glebe

This 3br 2ba home with own private beach is nestled off of the Potomac River and boasts serene and expansive views. Sunbathe on the private beach, cool off in the water, go fishing/crabbing from the dock, or just listen to the waves crash. Whatever it is, you’ll find it absolutely relaxing. Be sure to explore local wineries, breweries, shops and enjoy the community pool and tennis court. It's the perfect getaway house for couples/families or anyone looking for a serene weekend.

4.93 out of 5 average rating, 85 reviews

An inground pool is visible, featuring clear blue water gently reflecting sunlight. Lounge chairs are positioned along the pool's edge, with a tree-lined backdrop providing shade. A person swims in the deep end, while another relaxes on the side, enjoying the environment.

Home in Lexington Park

Serenity Bay-Priv Pool-ask about 2-night stays!

Now offering 2-night stays!! Send a message to ask about this! Spacious, relaxing, and scenic bay-view house with canoe/kayak access to the Chesapeake Bay. Six bedrooms and 5 full baths provide plenty of space for family and friends to enjoy time together. Plenty to do with an outdoor pool, an abundantly equipped recreation room, and a dock from which to launch your kayak or canoe. Easy access to plenty of activities in the surrounding area makes for a memorable vacation.

4.97 out of 5 average rating, 38 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

Nestled in a beautiful water community you'll find this modernized cottage. Harbor Cottage is a bright and open A-frame single family home, perfect for a quiet and cozy retreat. Relax on the four-season porch with panoramic views! Get outdoors and enjoy hiking, biking, bird watching or fossil hunting. A short 5 minute walk you'll find a sandy private beach perfect for sunbathing, shell collecting, fishing and stunning sunrises.

A spacious living room features a large sectional sofa complemented by two accent chairs, fostering a relaxed atmosphere. A mounted smart TV is positioned above a contemporary fireplace, with natural light streaming in through large windows. Decorative pieces and plants enhance the comfort of the space.

4.99 out of 5 average rating, 105 reviews

Waterfront Retreat Beach+Pool | Gamerm | Dog+EV OK

Relax ✧ Kayak ✧ Paddleboard ✧ Hike ✧ Fish ✧ Swim ✧ Beach & more at the Riverside Retreat in Montross! ☀️ Welcome to our modern waterfront sanctuary with kayaks + paddleboard 🏊‍♀️ 3 community beaches + pool (open Memorial to Labor Day) 👨‍🍳 Gas griddle for cooking a delicious meal 🔥 Fire pit + Gameroom (ping pong, arcade, & more!) 🐶 Dogs Welcome ⚡️EV Charging Book today or ❤️ us for next time

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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A charming riverfront home is framed by lush greenery and colorful flowerpots. A welcoming pathway leads to the front door, flanked by well-maintained garden beds. The expansive porch invites relaxation, with captivating views of the serene landscape visible in the distance.

4.88 out of 5 average rating, 8 reviews

New Private Beachfront panoramic view every window

KarenRating, 5 stars5 days ago

Michele an excellent hostess, her house is wonderful our family and our children enjoyed it to the fullest, we hope to return soon!!

A wooden dock extends into calm waters, featuring two boats secured at the end. A colorful sail with bright red, yellow, and blue stripes stands upright, contrasting with the clear blue sky. Surrounding greenery creates a serene backdrop.

4.98 out of 5 average rating, 44 reviews

Game-Themed Water Fun! Boats+Pool+Beach+King Bed

JenniferRating, 5 stars3 weeks ago

Easthaven is a gem! We thoroughly enjoyed our time there. Something to do for everyone, indoors and outdoors. Really nice to have the SUP and kayaks available, as well as the crab pots. So many thoughtful touches, probably the most well stocked home we’ve stayed in. Definitely hope to return in the future!

4.96 out of 5 average rating, 69 reviews

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

Heron Harbor

DianaRating, 5 stars34 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!!

5 out of 5 average rating, 6 reviews

The living room features three couches arranged around a glass coffee table, providing ample seating. A television is positioned for viewing, with light streaming through the large windows dressed with curtains. The warm tones of the wooden floors and brick wall create a cozy atmosphere.

Home in Charlotte Hall

Cozy Retreat w/ Pool: MIR & DC

NicoleRating, 5 stars1 month ago

This place was great! Justin was a GREAT host and the home was exactly what we needed while we were in town. The printed instructions on the fridge greatly helped us with the checkout procedures. The house was peaceful and cozy!

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.

4.86 out of 5 average rating, 7 reviews

Newly Renovated River Retreat w/Dock and Pool

JamieRating, 5 stars2 months 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 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.

4.93 out of 5 average rating, 80 reviews

Spacious and private waterfront, sleeps 10

MichaelRating, 5 stars2 months 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.

A living area features a modern television displaying a serene coastal scene. A light wooden cabinet with woven detailing is positioned beneath the screen. A round coffee table with a metallic finish sits in the center, accompanied by a decorative bowl and literature.

5 out of 5 average rating, 3 reviews

Bliss By The Bay Chalet

CamRating, 5 stars9 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.