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 Hollywood

4.85 out of 5 average rating, 26 reviews

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, kayak launch and gated boat launch 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.

Feb 24 – Mar 3

€ 132 per night

Guest favorite

Home in Montross

5.0 out of 5 average rating, 7 reviews

That 70's Hive - Retro Retreat w/ Beaches, Pool +

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.

Mar 21 – 28

€ 210 per night

Guest favorite

Home in Dameron

5.0 out of 5 average rating, 29 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

Jun 23 – 30

€ 1,140 per night

Guest favorite

Villa in Montross

5.0 out of 5 average rating, 21 reviews

Waterfront+DOCK+Beach+Kayak+Pddlebrd+Arcade

Our serene coastal space with expansive river views is just what you need! Sit back and take in the views, fish, crab or watch the waves and wildlife-dolphins, birds, etc. FEATURES - Water views from nearly every room - Beaches at the end of the street - Dock, fire pit, gas grill, outdoor chairs, arcade console table, cornhole, tennis rackets+pickle ball & more - Kayak, paddle boards & 4 life jackets - 4 crab pots & fishing poles - Clubhouse, pool (summer), tennis courts & more -WiFi & desk

Nov 3 – 10

€ 471 per night

Guest favorite

Home in Montross

5.0 out of 5 average rating, 47 reviews

Waterfront+Kayaks+Gameroom+Pool+Firepit+EV/Dog OK

★ Water access + Kayaks ★ Private deck & patio ★ Community Beaches (closest - 0.3 mi, largest - 1 mile) + Pool (~2.5 miles generally opens Memorial Day) ★ Game Room (ping pong/arcade/tv/games) ★ Solo Stove Fire Pit w/seating ★ Hammock ★ Fully Stocked Kitchen ★ Smart TVs ★ EV Outlet ★ Dogs OK (limit 2 w/ fee) Kayak✧Swim✧Hike✧Bird Watch✧Fish✧ Star Gaze✧Antique Shop Book your stay today or ♥ our listing to easily find us next time. For more photos/local info, see our IG: @variversideretreat

Oct 29 – Nov 5

€ 305 per night

Guest favorite

Home in Montross

5.0 out of 5 average rating, 120 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!

Oct 1 – 8

€ 441 per night

Superhost

Cottage in Heathsville

4.83 out of 5 average rating, 58 reviews

Riverfront Retreat with PRIVATE POOL and BEACH!!

Welcome to your riverfront retreat. Only a 2 hour drive from DC/RVA, this riverfront cottage has everything you need to get away. After spending time on your private beach, relax in your own pool, before spending the evening relaxing in the screened in porch or by the firepit. Sunny? Take out the kayaks, stand up paddle boards or cornhole. Rainy? The home is furnished with TVs, chromecasts, high speed internet, board games and puzzles. Follow us on IG @riverfront_retreat for more

Sep 11 – 18

€ 434 per night

Guest favorite

Villa in Hague

4.96 out of 5 average rating, 27 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!

Apr 11 – 18

€ 474 per night

Guest favorite

Home in Montross

4.93 out of 5 average rating, 166 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.

Dec 4 – 11

€ 263 per night

Superhost

Home in Saint Marys City

4.92 out of 5 average rating, 52 reviews

Historic Rosecroft

Magical. That’s the most often used descriptor of Rosecroft by visitors for the past 400 years. Dating back to 1639, 20+ acres including horses and chickens, Rosecroft is the site of a former plantation and home to Maryland’s first Tax Collector, when St. Mary’s City was the capital of Maryland. Steeped in history and natural beauty, you will enjoy sweeping water views and majestic trees, freedom to walk the grounds, and a unique opportunity to stay at a historic place.

May 3 – 10

€ 853 per night

Guest favorite

Cottage in Montross

4.94 out of 5 average rating, 17 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.

Jan 3 – 10

€ 221 per night

Guest favorite

Farm stay in Port Republic

5.0 out of 5 average rating, 93 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!

Dec 26 – Jan 2

€ 220 per night