
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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Vacation rentals for every style
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Popular amenities for St. Mary's County rentals with a pool
House rentals with a pool
Top guest favorite

Home in Abell
5 out of 5 average rating, 7 reviewsNew, Waterfront Home w/ Island on St. Clements Bay

Home in Saint Leonard
5 out of 5 average rating, 4 reviewsPool Oasis Upstairs Suite
Superhost

Home in Lottsburg
4.96 out of 5 average rating, 69 reviewsHeron Harbor
Top guest favorite

Home in Lusby
5 out of 5 average rating, 32 reviewsOsprey Eyrie on the Chesapeake•Pool•Beach•Firepit
Guest favorite

Home in Lusby
4.92 out of 5 average rating, 85 reviewsSpacious and private waterfront, sleeps 10
Top guest favorite

Home in Lusby
5 out of 5 average rating, 12 reviewsBliss By The Bay Chalet
Guest favorite

Home in Montross
4.86 out of 5 average rating, 7 reviewsSlice Of Heaven
Superhost

Home in Saint Leonard
5 out of 5 average rating, 3 reviewsSpacious Private Retreat on the Patuxent River
Other vacation rentals with a pool
Guest favorite

Home in Montross
4.98 out of 5 average rating, 119 reviews10/15-18 OPEN Waterfront | Gameroom+Kayak+Firepit
Superhost

Home in Montross
4.92 out of 5 average rating, 219 reviewsThe Glebe
Superhost

Guest suite in Saint Leonard
4.79 out of 5 average rating, 52 reviewsShewell’s Basement Studio at Long Beach

Home in Saint Leonard
POOL Oasis Basement Suite

Cabin in Drayden
Cabin 1 / Blue Heron Hideaway
Top guest favorite

Cottage in Montross
4.98 out of 5 average rating, 50 reviewsHarbor Cottage
Top guest favorite

Home in Montross
4.98 out of 5 average rating, 169 reviewsBeach Please! River cottage w/private beach & dock
Guest favorite

Home in California
4.96 out of 5 average rating, 26 reviewsWaterfront, pier, hot tub, pool, pizza oven
Destinations to explore
- Rentals with lake access St. Mary's County
- Rentals with a kayak St. Mary's County
- Waterfront rentals St. Mary's County
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- Rentals with a patio St. Mary's County
- Rentals with a fireplace St. Mary's County
- Apartment rentals St. Mary's County
- Rentals with breakfast St. Mary's County
- Beachfront rentals St. Mary's County
- Rentals with a hot tub St. Mary's County
- House rentals St. Mary's County
- Rentals with a fire pit St. Mary's County
- Rentals with a washer and dryer St. Mary's County
- Rentals with beach access St. Mary's County
- Rentals with outdoor seating St. Mary's County
- Pet-friendly rentals St. Mary's County
- Rentals with pools Maryland
- Rentals with pools United States
- Chesapeake Bay
- Haven Beach
- Bethel Beach
- Breezy Point Beach & Campground
- Piney Point Beach
- Ragged Point Beach
- Chesapeake Beach Water Park
- Gerry Boyle Park
- Sandyland Beach
- Rose Haven Memorial Park
- Bayfront Beach
- North Beach Boardwalk/Beach
- St George Island Beach
- Franklin Manor Community Private Park
- Guard Shore
- Brownies Beach
- Oxford Beach
- Langford Sand
- Lane Beach
- Layton's Chance Vineyard and Winery
- Ingleside Vineyards
- General's Ridge Vineyard
- Bordeleau Vineyards & Winery
- Neals Beach