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 Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
Feb 5 – 12
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
Jan 29 – Feb 5
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Oct 15 – 22
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
Oct 30 – Nov 6
Home in Shady Side
4.88 out of 5 average rating, 174 reviewsCattail Landing- Photographer's Waterfront Retreat
Jan 3 – 10
Home in Annapolis
4.95 out of 5 average rating, 41 reviewsNaptown Suite
Jul 24 – 31
Home in Edgewater
4.97 out of 5 average rating, 30 reviewsEntire Beach House with Pool and Hot Tub
Oct 31 – Nov 7
Home in Annapolis
4.94 out of 5 average rating, 62 reviewsSouth River Retreat, Annapolis MD
Mar 8 – 15
Condo rentals with a pool
Condo in McLean
4.82 out of 5 average rating, 128 reviews3 Bedroom/King-Master/Free-Parking/POOL (Rare)
Feb 22 – Mar 1
Condo in Oxon Hill
4.88 out of 5 average rating, 132 reviewsModern Apartments available at National Harbor
Jun 22 – 29
Condo in Annapolis
4.97 out of 5 average rating, 70 reviewsSpring into Annapolis-very low cleaning fee
Jan 25 – Feb 1
Condo in Annapolis
5.0 out of 5 average rating, 9 reviewsCharming Annapolis Waterfront Condo
Jan 25 – Feb 1
Condo in Annapolis
4.89 out of 5 average rating, 9 reviewsNewly Renovated 1-Bedroom on Spa Creek
Feb 24 – Mar 3
Condo in Annapolis
4.94 out of 5 average rating, 36 reviewsCozy Annapolis Condo
Dec 4 – 11
Condo in Alexandria
5.0 out of 5 average rating, 7 reviewsQuiet Condo Near Alexandria ~ Ideal for long stays
Condo in Alexandria
4.67 out of 5 average rating, 3 reviewsBeautiful 1 bedroom 1 bath apt in Alexandria VA
Feb 3 – 10
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
R743 ZAR before taxes and fees
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