Vacation rentals with a pool in Annapolis
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Annapolis
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Annapolis rentals with a pool
House rentals with a pool
Home in Edgewater
4.95 out of 5 average rating, 122 reviewsHouse in Edgewater Maryland
Home in Cambridge
4.96 out of 5 average rating, 101 reviewsWaterfront, Fabulous Home for Families with Pool!
Home in Harwood
4.94 out of 5 average rating, 118 reviewsLuxury Home, Sleeps 15, Private Pool, Close to DC
Home in Saint Michaels
4.97 out of 5 average rating, 240 reviewsMiles Aweigh
Home in New Market
4.93 out of 5 average rating, 117 reviewsHistoric Peace and Plenty Farm: Pool House
Home in Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
Home in Severn
4.82 out of 5 average rating, 105 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
Home in Fairfax
4.96 out of 5 average rating, 147 reviews6BR Modern Home w/HEATED Pool & Screened in Porch
Condo rentals with a pool
Condo in West Springfield
4.84 out of 5 average rating, 170 reviewsBeautiful 2BR/1BA Renovated Condo near DC
Condo in Oxon Hill
4.88 out of 5 average rating, 132 reviewsModern Apartments available at National Harbor
Condo in McLean
4.82 out of 5 average rating, 131 reviews3 Bedroom/King-Master/Free-Parking/POOL (Rare)
Condo in Annapolis
4.97 out of 5 average rating, 71 reviewsSpring into Annapolis-very low cleaning fee
Condo in Annapolis
4.89 out of 5 average rating, 9 reviewsNewly Renovated 1-Bedroom on Spa Creek
Condo in Annapolis
5.0 out of 5 average rating, 15 reviewsCharming Annapolis Waterfront Condo
Condo in Annapolis
4.95 out of 5 average rating, 37 reviewsCozy Annapolis Condo
Condo in McLean
4.98 out of 5 average rating, 83 reviewsLuxury 1bd in Heart of Tysons
Quick stats about vacation rentals with a pool in Annapolis
Total rentals
40 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.5K reviews
Nightly prices starting at
$40 before taxes and fees
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