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

Home in Ridge

4.89 out of 5 average rating, 54 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.

Superhost

Home in Dameron

5 out of 5 average rating, 33 reviews

Dameron Farm on the Water - Private Pool

15 Acre Waterfront Farm - Saltwater heated pool (seasonal)! - Private Beach - Contactless Check-In - Pet Friendly - Tesla Charger (with adapters for other EVs) - Free High Speed Wifi - Linens, Soaps and Shampoo Provided. ChesapeakeBayVacations (ig @ChesapeakeBayVacations) for more pics and information... Looking for something more cozy directly on the Bay? Be sure to check out our sister properties, Rodo Beach Cottage and Hays Beach House! Feel the Chesapeake breeze as soon as you arrive on t

Superhost

Home in Montross

4.93 out of 5 average rating, 28 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

Home in Montross

4.99 out of 5 average rating, 143 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!

Guest favorite

Villa in Hague

4.98 out of 5 average rating, 46 reviews

Sea Glass Paradise

The Seaglass Paradise is an amazing river front property close to Chesapeake Bay. Pets are welcome! Relax on the white sands with family and friends. Fish right off your own private dock, build a fire on the beach at night, and bring your boat ! Boat slips are available to rent at the Marina . Access to the marina pool included in your stay and just a short bike ride away. There is an indoor fireplace for those chillyfalll and winter nights. A Beautiful year round Vacation Home!

Guest favorite

Home in Lusby

5 out of 5 average rating, 15 reviews

Osprey Eyrie on the Chesapeake Bay

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.

Guest favorite

Home in Montross

4.94 out of 5 average rating, 189 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.

Guest favorite

Home in Hollywood

4.9 out of 5 average rating, 41 reviews

The Riverhouse

Quiet neighborhood where kids can go bike riding & adults can take a leisurely walk. View the Patuxent River from the front porch. Community pool within walking distance. 2 spacious bedrooms and 2 baths. Plenty of great restaurants, music venues and sightseeing in southern Maryland. Potomac River, Point Lookout State Park, Maryland International Raceway (MIR), Calvert Marine Museum, Solomons Island, close to DC for touring & only 90 minutes to Kings Dominion.

Guest favorite

Home in Montross

5 out of 5 average rating, 79 reviews

Waterfront Escape: Gameroom-Firepit-Dogs & EV OK

Discover Riverside Retreat, your waterfront sanctuary. Begin your morning with a cup of coffee on the back deck overlooking Betty's Pond, spend your afternoon exploring nearby towns and parks & conclude your day by cooking up a delicious meal on the deck, relaxing by the fire pit, or in our game room. High-speed Wi-Fi & a modern amenities ensure your stay is both connected & comfy. <3 us to find us easily next time or see us on IG: @variversideretreat

Guest favorite

Cottage in Montross

4.97 out of 5 average rating, 33 reviews

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.

Guest favorite

Farm stay in Port Republic

5 out of 5 average rating, 104 reviews

Maple Hollow Farm - A Little Piece of Heaven

Enjoy the modern farmhouse charm of this totally remodeled apartment here at Maple Hollow Farm! This space has been totally renovated and includes all new furnishings, appliances, amenities and unique, stylish decor. You will enjoy a spectacular view off the attached deck that typically includes the horses grazing in the pastures and an amazing sunset! It's a fabulous location for your next getaway or even stay-cation!

Guest favorite

Home in Lexington Park

4.92 out of 5 average rating, 77 reviews

Serenity Bay-Relaxing, Spacious House-Private Pool

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.