Vacation rentals with a pool in Calvert County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Calvert 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
Get the amount of space that is right for you
Popular amenities for Calvert County rentals with a pool
House rentals with a pool
Guest favorite
Home in Hollywood
4.86 out of 5 average rating, 29 reviewsRiverhouse
Superhost
Home in Lusby
4.91 out of 5 average rating, 68 reviewsSpacious and private waterfront, sleeps 10
Guest favorite
Home in California
4.93 out of 5 average rating, 14 reviewsWaterfront home with pier near Solomon's Island
Guest favorite
Home in Lusby
5.0 out of 5 average rating, 5 reviewsSerene and Private Waterfront Retreat w Pool
Guest favorite
Home in Owings
5.0 out of 5 average rating, 12 reviewsMills House on Patuxent River
Home in Port Republic
4.8 out of 5 average rating, 5 reviewsFamily Friendly: Hot Tub, Grill, Pool & More!
Guest favorite
Home in Tilghman Island
5.0 out of 5 average rating, 19 reviewsEnjoy a weekly stay discount in July!
Home in Lusby
5.0 out of 5 average rating, 3 reviewsNewly Renovated River Retreat
Condo rentals with a pool
Guest favorite
Condo in Annapolis
4.97 out of 5 average rating, 71 reviewsSpring into Annapolis-very low cleaning fee
Guest favorite
Condo in Annapolis
5.0 out of 5 average rating, 17 reviewsCharming Annapolis Waterfront Condo
Guest favorite
Condo in Annapolis
4.89 out of 5 average rating, 9 reviewsNewly Renovated 1-Bedroom on Spa Creek
Guest favorite
Condo in Colonial Beach
5.0 out of 5 average rating, 25 reviewsRooftop bay and river views
Superhost
Condo in Annapolis
4.5 out of 5 average rating, 4 reviewsWalk to Main St Waterfront condo, pool, parking
Guest favorite
Condo in Annapolis
4.95 out of 5 average rating, 37 reviewsCozy Annapolis Condo
Guest favorite
Condo in Annapolis
4.96 out of 5 average rating, 223 reviewsAnnapolis Waterfront Condo - Unit #: A-203
Guest favorite
Condo in Annapolis
4.88 out of 5 average rating, 58 reviewsGREAT LOCATION ON SPA CREEK
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