Vacation rentals with a pool in St. Mary's County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in St. Mary's County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

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

4.87 out of 5 average rating, 61 reviews

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.

Top guest favorite

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.

Home in Montross

4.95 out of 5 average rating, 20 reviews

New Private Beachfront panoramic view every window

This luxurious waterfront home has its own private beach exclusive to this property with unmatched panoramic views from almost every room in the house. Perfect for a quiet family getaway where you are looking to just unplug and enjoy the water! This home has everything you need including a fully stocked kitchen, appliances, washer/dryer machines, a screened in porch, 2 open decks off (sunroom & primary suite). Enjoy an evening hanging with the family in the movie room or catch the best sunsets!

Guest favorite

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.

Home in Montross

4.93 out of 5 average rating, 44 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.

Guest favorite

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.

Home in Montross

4.98 out of 5 average rating, 114 reviews

3N PROMO | Waterfront | Beach+Gamerm+Kayak/Pddlbd

*Ask about our 3N+ promotions* ☀️ Waterfront 🛶 Kayak/Paddleboard 👨‍🍳 Gas griddle ⛱️ 3 Community Beaches 🔥 Fire pit 🐶 Dogs OK 🎯 Gameroom ⚡️EV Outlet Whether you're looking to take a break or connect with nature, the Riverside Retreat in Montross, VA offers a peaceful sanctuary that is perfect for families, small groups, & couples. Relax - Star Gaze - Kayaks - Paddleboard - Hike - Fish - Swim - Beach & more! Book your getaway today or ❤️ us for next time!

Guest favorite

Home in Montross

4.98 out of 5 average rating, 165 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!

Superhost

A view of the modern house showcases its two-story design with a green metal roof. Surrounding the inviting in-ground pool are landscaped gardens and pots with small plants. The outdoor area provides a serene setting, complemented by vibrant greenery in the background.

Home in Saint Leonard

5 out of 5 average rating, 3 reviews

Spacious Private Retreat on the Patuxent River

Perched at the point of 55 wooded acres with water on three sides, this modern complex is the epitome of outdoor living in peace and seclusion. Grill on the tip of the peninsula and soak in the views. Living room/kitchen areas are designed for gatherings, as are the twin 100 ft covered porches, while the dock leads to a stunning private cove. The annex provides a cozy retreat with two bedrooms, bathroom, kitchen/den and deck with water views. Lounge by the pool or take a dip to cool off.

Guest favorite

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.

Home in Montross

4.93 out of 5 average rating, 60 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.

Guest favorite

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

4.95 out of 5 average rating, 19 reviews

Cozy Retreat w/ Pool: MIR & DC

Relax in this spacious 4-bedroom, 1-bath home with a private pool (open May 13th - September 1st) perfect for families or groups. The Maryland International Raceway and Budds Creek Motocross Park are only 7 miles away, making this an ideal spot for race fans...and we have plenty of parking for your race trailers or cars. Washington, D.C. is also just a short drive. With a prime location and plenty of space to unwind, this home offers comfort and convenience for your next getaway.

Top guest favorite

The historic home features a charming exterior with a mix of white clapboard and dark shingles. An inviting porch is framed by green shutters and surrounded by well-maintained landscaping. A gravel driveway leads to the front entrance, enhancing the property’s welcoming appeal.

Home in Lusby

5 out of 5 average rating, 149 reviews

Historic Rousby Hall, Waterfront, Pool, Beach

*Heated pool open to Nov 2* Rousby Hall is a stunning 5-star waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool (May–October) with amazing river views. The estate also hosts weddings and events for up to 100 guests (additional event fee applies).

Superhost

Home in Montross

4.92 out of 5 average rating, 214 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.

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, 107 reviews

Beach Retreat

Relax with the whole family at the Beach Retreat! Enjoy the beautiful Sunrise and Sunsets in the Hot tub overlooking your own private beach! There is plenty to do in the Northern Neck of Virginia! We have Wineries, a Brewery, historical sites, boating, swimming, fires on the beach, bike rides, kayaking, plenty of Summer and Fall Festivals and so many great places to eat on and off the river! The Northern Neck of VA is a hidden gem! Just a 90 minute drive from the DC area

Guest favorite

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

4.93 out of 5 average rating, 91 reviews

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.