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 New Market
4.94 out of 5 average rating, 115 reviewsHistoric Peace and Plenty Farm: Pool House
Mar 19 – 26
Home in Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
Feb 2 – 9
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
Dec 6 – 13
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Nov 22 – 29
Home in Fairfax
4.96 out of 5 average rating, 146 reviews6BR Modern Home w/HEATED Pool & Screened in Porch
Dec 27 – Jan 3
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
Feb 5 – 12
Home in Shady Side
4.88 out of 5 average rating, 174 reviewsCattail Landing- Photographer's Waterfront Retreat
Oct 2 – 9
Home in Annapolis
4.95 out of 5 average rating, 41 reviewsNaptown Suite
Jun 29 – Jul 6
Condo rentals with a pool
Condo in McLean
4.82 out of 5 average rating, 127 reviews3 Bedroom/King-Master/Free-Parking/POOL (Rare)
Jan 24 – 31
Condo in Oxon Hill
4.88 out of 5 average rating, 132 reviewsModern Apartments available at National Harbor
Jun 20 – 27
Condo in Annapolis
4.97 out of 5 average rating, 70 reviewsSpring into Annapolis-very low cleaning fee
Jan 28 – Feb 4
Condo in Annapolis
5.0 out of 5 average rating, 8 reviewsCharming Annapolis Waterfront Condo
Sep 21 – 28
Condo in Annapolis
4.89 out of 5 average rating, 9 reviewsNewly Renovated 1-Bedroom on Spa Creek
Oct 31 – Nov 7
Condo in Annapolis
4.94 out of 5 average rating, 36 reviewsCozy Annapolis Condo
Dec 1 – 8
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 12 – 19
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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