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.

Guest favorite
Home in Montross
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!
Mar 6 – 13
$314 per night
5.0 out of 5 average rating, 115 reviews
Superhost
Cottage in Heathsville
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 19 – 26
$338 per night
4.82 out of 5 average rating, 57 reviews
Guest favorite
Home in Montross
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.
Nov 27 – Dec 4
$224 per night
4.93 out of 5 average rating, 160 reviews

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

House rentals with a pool

Guest favorite
Home in Hollywood
Riverhouse
Oct 29 – Nov 5
$100 per night
4.83 out of 5 average rating, 24 reviews
Guest favorite
Home in California
Waterfront home with pier near Solomon's Island
Mar 8 – 15
$191 per night
4.93 out of 5 average rating, 14 reviews
Guest favorite
Home in Hague
Year-Round River Escape with Indoor Pool & Beach
Feb 16 – 23
$987 per night
4.96 out of 5 average rating, 81 reviews
Guest favorite
Home in Montross
Waterfront+Kayak+Gameroom+Arcade+Firepit+EV/Dog OK
Sep 26 – Oct 3
$403 per night
5.0 out of 5 average rating, 41 reviews
Guest favorite
Home in Fishing Creek
Bay Front Villa on Chesapeake
Nov 7 – 14
$882 per night
4.89 out of 5 average rating, 9 reviews
Guest favorite
Home in Montross
River Retreat
Nov 2 – 9
$950 per night
4.96 out of 5 average rating, 55 reviews
Guest favorite
Home in Montross
Waterfront Dock, Hot Tub, Beach, Pool, Kayaks, SUP
Aug 2 – 9
$922 per night
4.96 out of 5 average rating, 69 reviews
Guest favorite
Home in Lusby
Spacious and private waterfront, sleeps 10
Sep 21 – 28
$159 per night
4.91 out of 5 average rating, 65 reviews
Guest favorite
Home in Lottsburg
Heron Harbor
Jan 21 – 28
$563 per night
4.96 out of 5 average rating, 69 reviews
Guest favorite
Home in Lusby
Serene and Private Waterfront Retreat w Pool
Feb 18 – 25
$636 per night
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Taylors Island
The Marina Oasis in Taylors Island
Aug 31 – Sep 7
$173 per night
4.7 out of 5 average rating, 82 reviews
Superhost
Home in Montross
That 70's Hive - Retro Retreat w/ Beaches, Pool +
Feb 9 – 16
$151 per night
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