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 Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
Home in Shady Side
4.88 out of 5 average rating, 174 reviewsCattail Landing- Photographer's Waterfront Retreat
Home in Annapolis
4.95 out of 5 average rating, 41 reviewsNaptown Suite
Home in Edgewater
4.97 out of 5 average rating, 30 reviewsEntire Beach House with Pool and Hot Tub
Home in Annapolis
4.94 out of 5 average rating, 62 reviewsSouth River Retreat, Annapolis MD
Home in Stevensville
4.98 out of 5 average rating, 63 reviewsBeautiful Kent Island Getaway with Pool
Home in Stevensville
5.0 out of 5 average rating, 35 reviewsThe Pool House in Romancoke On The Bay
Home in Edgewater
4.97 out of 5 average rating, 31 reviewsWaterfront | Pool | Hot tub | Beach Access
Condo rentals with a pool
Condo in Annapolis
4.97 out of 5 average rating, 70 reviewsSpring into Annapolis-very low cleaning fee
Condo in Annapolis
5.0 out of 5 average rating, 9 reviewsCharming Annapolis Waterfront Condo
Condo in Annapolis
4.89 out of 5 average rating, 9 reviewsNewly Renovated 1-Bedroom on Spa Creek
Condo in Annapolis
4.94 out of 5 average rating, 36 reviewsCozy Annapolis Condo
Condo in Baltimore
5.0 out of 5 average rating, 5 reviewsArchitect's Home - Historic w/ Contemporary Design
Condo in Annapolis
4.5 out of 5 average rating, 4 reviewsWalk to Main St Waterfront condo, pool, parking
Condo in Annapolis
4.96 out of 5 average rating, 217 reviewsAnnapolis Waterfront Condo - Unit #: A-203
Condo in Annapolis
4.88 out of 5 average rating, 58 reviewsGREAT LOCATION ON SPA CREEK
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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- Rentals with pools United States
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